8-Oxo-5-aza-spiro[2.5]octane-5-carboxylic acid benzyl ester,

str2

1H NMR PREDICT OF TITLE COMPD

…………………………………
13C NMR PREDICT

……………….

8-Oxo-5-aza-spiro[2.5]octane-5,7-dicarboxylic acid 5 benzyl ester 7 methyl ester
COMPD 5

SYNTHESIS CONSTRUCTION BY WORLDDRUGTRACKER………EXCLUSIVE

 

सुकून उतना ही देना प्रभू, जितने से जिंदगी चल जाये। औकात बस इतनी देना, कि औरों का भला हो जाये।
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09b37-misc2b027LIONEL MY SON
He was only in first standard in school when I was hit by a deadly one in a million spine stroke called acute transverse mylitis, it made me 90% paralysed and bound to a wheel chair, Now I keep him as my source of inspiration and helping millions, thanks to millions of my readers who keep me going and help me to keep my son happy
सुकून उतना ही देना प्रभू, जितने से
जिंदगी चल जाये।
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कि औरों का भला हो जाये।

 

////////////

7-allyl-6-hydroxy-indan-1-one…Mom will teach you NMR

Figure US08242291-20120814-C00009

Thermal Claisen rearrangement on 6-allyloxy-indan-1-one,  (III) to obtain 7-allyl-6-hydroxy-indan-1-one, (IV):

  • Formula: C12H12O2
  • Molecular Weight: 188.22200
Synonyms:

http://www.google.com/patents/US8242291
EXAMPLE 2

This example refers to reaction b of the process of the invention.
20 kg of the intermediate of formula (III) prepared as described in example 1 are suspended in 50 l of Dowtherm A under nitrogen flow. In an inert atmosphere, it is heated to approximately 200° C. for approximately 5 hours. Upon completion of the reaction (TLC) a clear red-brown solution is obtained, without the formation of black pitch. The reaction mixture is cooled slowly to 25° C. (a partial precipitation is observed). 100 l (5 volumes) of cyclohexane are added and it is cooled to between 0 and 5° C. for one hour. It is filtered by washing with cyclohexane and dried at reduced pressure and T=45° C. for at least 12 hours. 16.8 kg of yellow solid are obtained which is refluxed in 80 l of toluene in the presence of decolouring carbon. The suspension is filtered, washing it with hot toluene. Part of the solvent is distilled at reduced pressure until the beginning of crystallisation. It is cooled at room temperature and then to between 0 and 5° C. for at least one hour.
The filtered solid is washed with cold toluene and dried at reduced pressure at T=45° C. for at least 12 hours. 15.3 kg of intermediate (IV) are obtained in the form of an almost white solid of quality suitable for continuation of the synthesis.
1H-NMR and mass spectroscopic analyses are performed on part of the product thus obtained, purified by chromatography for analytical purposes (silica gel, 7 parts in volume of heptane—3 parts in volume of ethyl acetate), obtaining the following results:
Electron impact mass: [M+]=188
1H-NMR (500 MHz, CDCl3): δ (ppm)
2.72 ppm, t, J=6 Hz, 2H,  AR C=OCH2 CH2 AR
3.03 ppm, t, J=6 Hz, 2H, AR C=OCH2 CH2 AR
4.03 ppm, d, J=6 Hz, 2H, ARCH2CH=CH2
5.13-5.20, Σd, 2H, ARCH2CH=CH2
5.60 ppm, s, 1H, 0H
5.98-6.10 ppm, m, 1H, CH2CH=CH2
7.13 ppm, d, J=8 Hz, 1H, AR
7.25, d, J=8 Hz, 1H. AR
PREDICT
1H NMRCLICK ON PICTURE

6-hydroxy-7-prop-2-enyl-2,3-dihydroinden-1-one NMR spectra analysis, Chemical CAS NO. 320574-77-4 NMR spectral analysis, 6-hydroxy-7-prop-2-enyl-2,3-dihydroinden-1-one H-NMR spectrum13 C NMR

CLICK ON PICTURE

6-hydroxy-7-prop-2-enyl-2,3-dihydroinden-1-one NMR spectra analysis, Chemical CAS NO. 320574-77-4 NMR spectral analysis, 6-hydroxy-7-prop-2-enyl-2,3-dihydroinden-1-one C-NMR spectrum
6-hydroxy-7-prop-2-enyl-2,3-dihydroinden-1-one

COSY PREDICT

HMBC PREDICT

…………….
COCK SAYS MOM CAN TEACH YOU NMR

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Your Aunt can teach you Organic Opectroscopy

Organic spectroscopy should be brushed up and you get confidence

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Organic chemists from Industry and academics to interact on Spectroscopy techniques for Organic compounds ie NMR, MASS, IR, UV Etc. email me ……….. amcrasto@gmail.com

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Oleanolic acid spectral data and interpretation

 http://orgspectroscopyint.blogspot.in/2014/08/oleanolic-acid-spectral-data-and.html
Chemical structure for Oleanolic AcidOleanolic acidOleanolic acid
(4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid

Oleanic acid, Caryophyllin, Astrantiagenin C, Giganteumgenin C, Virgaureagenin B, 3beta-Hydroxyolean-12-en-28-oic acid, OLEANOLIC_ACID
Molecular Formula: C30H48O3
Molecular Weight: 456.70032

http://orgspectroscopyint.blogspot.in/2014/08/oleanolic-acid-spectral-data-and.html

Ursolic acid [(3b)-3-Hydroxyurs-12-en-28-oic acid] rarely occurs without its isomer oleanolic acid [(3b)-3-Hydroxyolean-12-en-28-oic acid] They may occur in their free acid form, as shown in Figure 1, or as aglycones for triterpenoid saponins which are comprised of a triterpenoid aglycone linked to one or more sugar moieties. Ursolic and oleanolic acids are similar in pharmacological activity

A pentacyclic triterpene that occurs widely in many PLANTS as the free acid or the aglycone for many SAPONINS. It is biosynthesized from lupane. It can rearrange to the isomer, ursolic acid, or be oxidized to taraxasterol and amyrin.

MS
EIMS m/z (rel. int.) 456 [M]+ (5), 412 (3), 248 (100), 203 (50), 167 (25), 44 (51)

IR KBR
(KBr) 3500, 2950, 2850, 1715; 1H-NMR (250 MHz, pyridine-d5) δ: 5.49 (1H, s, H-12), 3.47 (1H, t, J = 8.0 Hz, H-3), 3.30 (1H, m, H-18), 1.12 (3H, s, CH3-27), 0.96 (3H, s, CH3-30), 0.91 (3H, s, CH3-25), 0.89 (3H, s, CH3-23), 0.87 (3H, s, CH3-24), 0.75 (3H, s, CH3-26)

http://orgspectroscopyint.blogspot.in/2014/08/oleanolic-acid-spectral-data-and.html

1H NMR

(250 MHz, pyridine-d5)δ: 5.49 (1H, s, H-12), 3.47 (1H, t, J = 8.0 Hz, H-3), 3.30 (1H, m, H-18), 1.12 (3H, s, CH3-27), 0.96 (3H, s, CH3-30), 0.91 (3H, s, CH3-25), 0.89 (3H, s, CH3-23), 0.87 (3H, s, CH3-24), 0.75 (3H, s, CH3-26)

13 C NMR

(63 MHz, pyridine-d5) δ: 180.2 (C-28), 144.8 (C-13), 122.5 (C-12), 78.0 (C-3), 55.7 (C-5), 48.0 (C-9), 46.6 (C-8, 17), 42.1 (C-14), 39.7 (C-4), 39.4 (C-1), 37.3 (C-10), 33.2 (C-7), 32.9 (C-29), 32.4 (C-21), 30.9 (C-20), 28.7 (C-23), 27.2 (C-2), 26.9 (C-15), 26.1 (C-30), 23.7 (C-11), 23.6 (C-16), 18.7 (C-6), 17.4 (C-26), 16.5 (C-24), 15.5 (C-25)

http://orgspectroscopyint.blogspot.in/2014/08/oleanolic-acid-spectral-data-and.html

http://www.google.com/patents/US20120237629

FIG. 4 shows the 1H NMR spectrum of oleanolic acid;
FIG. 5 shows the 13C NMR spectrum of oleanolic acid;
FIG. 6 shows the 13C DEPT NMR spectrum of oleanolic acid;
FIG. 7 shows the 113C HSQC NMR spectrum of oleanolic acid;
see below

http://orgspectroscopyint.blogspot.in/2014/08/oleanolic-acid-spectral-data-and.html

EXAMPLE 2 Extraction and Isolation of Oleanolic Acid (9) and Maslinic Acid (10) from Cloves

Syzygium aromaticum dried buds or whole cloves were obtained commercially. The cloves (1.5 kg, whole) of Syzygium aromaticum were sequentially and exhaustively extracted with hexane and ethyl acetate to give, after solvent removal in vacuo, a hexane extract (68.8 g, 4.9%) and an ethyl acetate extract (34.1 g, 2.3%). A portion of the ethyl acetate extract (10.0 g), was subjected to chromatographic separation on silica gel (60-120 mesh) column (40×5.0 cm). Elution with hexane/ethyl acetate solvent mixtures (8:2→6:4) afforded pure oleanolic acid (9) (4.7 g, 1.06%), a mixture of oleanolic acid (9) and maslinic acid (10) (0.5 g), and pure maslinic acid (10) (0.25 g). The structures of oleanolic acid (9) and maslinic acid (10) (as 2,3-diacetoxyoleanolic acid) were confirmed by spectroscopic data analysis (1D and 2D 1H NMR and 13C NMR experiments) (FIGS. 4-7 and FIGS. 8-10, respectively).
ANTHONY MELVIN CRASTO

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Oleanolic acid spectral data and interpretation

Oleanolic acid spectral data and interpretation

Chemical structure for Oleanolic Acid

Oleanolic acid

Oleanolic acid
(4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid

see full interpretation, 1H NMR, 13C NMR at

Ethyl acetoacetate 乙酰乙酸乙酯 teaches you Organic spectroscopy… brush up?????

read at

http://orgspectroscopyint.blogspot.in/2014/04/ethyl-acetoacetate-teaches-you-organic.html

Ethyl acetoacetate
Ethyl 3-oxobutanoate
Acetoacetic acid ethyl ester
Ethyl acetylacetate
3-Oxobutanoic acid ethyl ester


Ethyl acetoacetate is produced industrially by treatment of diketene with ethanol.
The preparation of ethyl acetoacetate is a classic laboratory procedure.[2] It is prepared via the Claisen condensation of ethyl acetate. Two moles of ethyl acetate condense to form one mole each of ethyl acetoacetate and ethanol.

Preparation of ethyl acetoacetate.







Structure: structure

IUPAC Name: ethyl 3-oxobutanoate (ethyl acetoacetate)

Analysis: C6H10O3: MW = 130.14

The molecule contains an oxygen, and from the analysis, contains two double bonds, carbonyls or rings.
The mass spectrum displays a molecular ion and the base peak represents the formation of the acylium ion, indicating the presence of a methyl adjacent to a carbonyl. The presence of an m-45 peak strongly suggests the presence of an ethoxy group.
The 13C spectrum contains six peaks, indicating that all carbons are unique. The quartets at  14 and 24 represent relatively simple methyl groups; the triplets at  59 and 47 represent a CH2 groups bonded to mildly electronegative groups; the singlets at  207 and 172 are in the carbonyl region, and most likely a ketone or aldehyde ( 207) and an ester ( 172).
The proton NMR shows evidence for an ethyl group and isolated CH2 and CH3 groups. The methylene of the ethyl group must be next to an electronegative atom (most likely oxygen) suggesting an -OCH2CH3 group. The isolated CH2 must also be flanked by mildly electronegative groups, and the isolated CH3 is in the region often observed for methyls adjacent to carbonyls.
The IR is consistent with a simple saturated hydrocarbon, possibly containing two carbonyls (based on the side peak at  1670 cm1). The minor peak at 3400 cm1 is too small to be an -OH.
The simplest structure which is consistent with all of these data would be a dicarbonyl compound containing an ethoxy residue and a methyl ketone (based on the presence of the acylium ion in the MS).

http://orgspectroscopyint.blogspot.in/2014/04/ethyl-acetoacetate-teaches-you-organic.html
………………….

1H NMR
NMR Spectrum
The proton NMR has a quartet coupled to a triplet, indicative of an ethyl group. The CH2 must be adjacent to an electron withdrawing group since it is shifted to  4.1. The two singlets at  2.2 and 3.2 suggest isolated CH2 and CH3 groups and the CH2 must be adjacent to one or more electronegative groups.

 

http://orgspectroscopyint.blogspot.in/2014/04/ethyl-acetoacetate-teaches-you-organic.html



http://orgspectroscopyint.blogspot.in/2014/04/ethyl-acetoacetate-teaches-you-organic.html
……………………………………………………….
13C NMR
13C NMR Assignments: C-13 assignments
13C NMR Data: q-13.6; q-24.2; t-59.2; t-46.6; s-172.0; s-207.1
The 13C spectrum contains six peaks, indicating that all carbons are unique. The quartets at  14 and 24 represent relatively simple methyl groups; the triplets at  59 and 47 represent a CH2 groups bonded to mildly electronegative groups; the singlets at  207 and 172 are in the carbonyl region, and most likely a ketone or aldehyde ( 207) and an ester ( 172).

spectrum for Ethyl acetoacetate

ethyl acetoacetate CH3COCH2COOCH2CH3

…………………………..

MASS SPECTROSCOPY
Mass Spectrum


Mass Spectrum Fragments: C-13 assignments
The mass spectrum consists of a molecular ion at 130, an m-15 peak at 115, which is consistent with loss of a CH3 group, an m-43 peak (loss of acylium), an m-45 peak (loss of CH3CH2O-), and a base peak at m-43(m/e = 43) which suggests the formation of an acylium ion (CH3-CO). The spectrum is consistent with a molecule which can lose methyl or ethoxy radicals, or can undergo fragmentation to form the acylium radical cation.

………………………….

IR

3400-3200 cm1: no OH peak (too small) 3100 cm1: no significant peak, suggesting no unsaturated CH 2900 cm1: strong peak suggesting saturated CH 2200 cm1: no unsymmetrical triple bonds 1710 cm1: strong carbonyl with a second peak at 1670 cm1, suggesting a the possibility of two carbonyls 1600 cm1: no significant peaks, suggesting no carbon-carbon double bonds

http://orgspectroscopyint.blogspot.in/2014/04/ethyl-acetoacetate-teaches-you-organic.html

2D [1H,1H]-TOCSY

spectrum for Ethyl acetoacetate

spectrum for Ethyl acetoacetate1D DEPT135





spectrum for Ethyl acetoacetate2D [1H,13C]-HSQC



spectrum for Ethyl acetoacetate2D [1H,13C]-HMBC





spectrum for Ethyl acetoacetate2D [1H,1H]-COSY


spectrum for Ethyl acetoacetate2D [1H,13C]-HMQC

 

http://orgspectroscopyint.blogspot.in/2014/04/ethyl-acetoacetate-teaches-you-organic.html

2D NMR SPECTRA INTERPRETATIONS–How To Read COSY Spectra

Two-dimensional nuclear magnetic resonance spectroscopy (2D NMR) is a set of nuclear magnetic resonance spectroscopy(NMR) methods which give data plotted in a space defined by two frequency axes rather than one. Types of 2D NMR includecorrelation spectroscopy (COSY), J-spectroscopyexchange spectroscopy (EXSY), and Nuclear Overhauser effect spectroscopy (NOESY). Two-dimensional NMR spectra provide more information about a molecule than one-dimensional NMR spectra and are especially useful in determining the structure of a molecule, particularly for molecules that are too complicated to work with using one-dimensional NMR.

The first two-dimensional experiment, COSY, was proposed by Jean Jeener, a professor at the Université Libre de Bruxelles, in 1971. This experiment was later implemented by Walter P. Aue, Enrico Bartholdi and Richard R. Ernst, who published their work in 1976.

LEARN MORE AT

http://faculty.sdmiramar.edu/fgarces/LabMatters/Instruments/NMR/Spectra_Interp/Reading2D_Spectrum.htm

 

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