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1H-Indene-2-carboxylic acid, 2,3-dihydro-1-oxo-, 1-methylethyl ester
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BASIC PARAMETERS
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CAS: 375349-04-5
MF: C13H14O3
MW: 218.24846
Synonyms: 1H-Indene-2-carboxylic acid, 2,3-dihydro-1-oxo-, 1-methylethyl ester
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ZhenJiang Xu
The Shanghai Institute of Organic Chemistry
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Yulai Hu
Northwest Normal University
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DanFeng Huang
Northwest Normal University
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Ying Fu
Northwest Normal University
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ZhanXian Gao
Dalian University of Technology
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Qingwei Meng
Dalian University of Technology
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Enantioselective α-chlorination of β-oxo esters catalyzed by chiral diterpenoid alkaloid derivatives
Co-reporter:
Zhi Li, Fan Yang, Qingwei Meng, Zhanxian Gao
pp:
1215-1220
Publication Date(Web):
15 September 2014
DOI:
10.1016/j.tetasy.2014.07.004
Easily accessible diterpenoid alkaloid derivatives have been used as organocatalysts in the enantioselective α-chlorination of β-oxo esters. The treatment of β-oxo esters with N-chlorophthalimide (NCP) as a chlorine source under mild reaction conditions afforded the corresponding α-chlorinated β-oxo esters in excellent yields (up to 98%) and with moderate enantioselectivities (up to 68% ee) in 30 min.
LappaconitineC32H44N2O8Source of chirality: natural occurrenceAbsolute configuration: (1S,4S,5S,7S,8S,9S,10S,11S,13R,14S,16S,17S)[α]D20 = +29.25 (c 0.40, MeOH)
VincamineC21H26N2O3Source of chirality: natural occurrenceAbsolute configuration: (3S,14S,16S)[α]D20 = +11.5 (c 0.51, CH2Cl2)
VinpocetineC21H24N2O2Source of chirality: natural occurrenceAbsolute configuration: (3S,16S)[α]D20 = +130.3 (c 0.50, CH2Cl2)
CytisineC11H14N2OSource of chirality: natural occurrenceAbsolute configuration: (1R,5S)[α]D20 = −111.9 (c 0.51, MeOH)
GalantamineC17H21NO3Source of chirality: natural occurrenceAbsolute configuration: (4αS,6R,8αS)[α]D20 = −117.0 (c 0.49, MeOH)
SinomenineC19H23NO4Source of chirality: natural occurrenceAbsolute configuration: (9S,13R,14S)[α]D20 = −87.2 (c 0.52, MeOH)
N-DeethyllappaconitineC30H40N2O8Source of chirality: lappaconitineAbsolute configuration: (1S,4S,5S,7S,8S,9S,10S,11S,13R,14S,16S,17S)[α]D20 = +42.7 (c 0.52, MeOH)
N-Methyl-N-deethyllappaconitineC31H42N2O8Source of chirality: lappaconitineAbsolute configuration: (1S,4S,5S,7S,8S,9S,10S,11S,13R,14S,16S,17S)[α]D20 = +27.2 (c 0.50, MeOH)
N-Benzyl-N-deethyllappaconitineC37H46N2O8Source of chirality: lappaconitineAbsolute configuration: (1S,4S,5S,7S,8S,9S,10S,11S,13R,14S,16S,17S)[α]D20 = +14.95 (c 0.50, MeOH)
LappaconineC23H37NO6Source of chirality: lappaconitineAbsolute configuration: (1S,4S,5S,7S,8S,9S,10S,11R,13R,14S,16S,17S)[α]D20 = +15.45 (c 0.51, MeOH)
4-BenzyloxylappaconineC30H43NO6Source of chirality: lappaconineAbsolute configuration: (1S,4S,5S,7S,8S,9S,10S,11S,13R,14S,16S,17S)[α]D20 = +2.3 (c 0.49, MeOH)
8,9-(Methylenedioxy)lappaconineC24H37NO6Source of chirality: lappaconineAbsolute configuration: (1S,4S,5S,7S,8S,9S,10S,11R,13R,14S,16S,17S)[α]D20 = +13.6 (c 0.50, CHCl3)
Jingping Qu
Dalian University of Technology
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Yunpeng LU
Nanyang Technological University
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Baomin Wang
Dalian University of Technology
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Da-Ming Du
Beijing Institute of Technology
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LappaconitineC32H44N2O8Source of chirality: natural occurrenceAbsolute configuration: (1S,4S,5S,7S,8S,9S,10S,11S,13R,14S,16S,17S)[α]D20 = +29.25 (c 0.40, MeOH)
VincamineC21H26N2O3Source of chirality: natural occurrenceAbsolute configuration: (3S,14S,16S)[α]D20 = +11.5 (c 0.51, CH2Cl2)
VinpocetineC21H24N2O2Source of chirality: natural occurrenceAbsolute configuration: (3S,16S)[α]D20 = +130.3 (c 0.50, CH2Cl2)
CytisineC11H14N2OSource of chirality: natural occurrenceAbsolute configuration: (1R,5S)[α]D20 = −111.9 (c 0.51, MeOH)
GalantamineC17H21NO3Source of chirality: natural occurrenceAbsolute configuration: (4αS,6R,8αS)[α]D20 = −117.0 (c 0.49, MeOH)
SinomenineC19H23NO4Source of chirality: natural occurrenceAbsolute configuration: (9S,13R,14S)[α]D20 = −87.2 (c 0.52, MeOH)
N-DeethyllappaconitineC30H40N2O8Source of chirality: lappaconitineAbsolute configuration: (1S,4S,5S,7S,8S,9S,10S,11S,13R,14S,16S,17S)[α]D20 = +42.7 (c 0.52, MeOH)
N-Methyl-N-deethyllappaconitineC31H42N2O8Source of chirality: lappaconitineAbsolute configuration: (1S,4S,5S,7S,8S,9S,10S,11S,13R,14S,16S,17S)[α]D20 = +27.2 (c 0.50, MeOH)
N-Benzyl-N-deethyllappaconitineC37H46N2O8Source of chirality: lappaconitineAbsolute configuration: (1S,4S,5S,7S,8S,9S,10S,11S,13R,14S,16S,17S)[α]D20 = +14.95 (c 0.50, MeOH)
LappaconineC23H37NO6Source of chirality: lappaconitineAbsolute configuration: (1S,4S,5S,7S,8S,9S,10S,11R,13R,14S,16S,17S)[α]D20 = +15.45 (c 0.51, MeOH)
4-BenzyloxylappaconineC30H43NO6Source of chirality: lappaconineAbsolute configuration: (1S,4S,5S,7S,8S,9S,10S,11S,13R,14S,16S,17S)[α]D20 = +2.3 (c 0.49, MeOH)
8,9-(Methylenedioxy)lappaconineC24H37NO6Source of chirality: lappaconineAbsolute configuration: (1S,4S,5S,7S,8S,9S,10S,11R,13R,14S,16S,17S)[α]D20 = +13.6 (c 0.50, CHCl3)