(1S)-3-氧代-环戊烷乙酸 | 2630-37-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (1S)-3-氧代-环戊烷乙酸
• 英文名称: 3-(hydroxycarbonylmethyl)cyclopentan-1-one
• 英文别名: (S)-2-(3-Oxocyclopentyl)acetic acid；2-[(1S)-3-oxocyclopentyl]acetic acid
• CAS: 2630-37-7
• 化学式: C₇H₁₀O₃
• 分子量: 142.155
• InChiKey: NNTQQGRYWUZPQQ-YFKPBYRVSA-N

物化性质

• 沸点：
  316.5±15.0 °C(Predicted)
• 密度：
  1.210±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲醇 、 (1S)-3-氧代-环戊烷乙酸 在 盐酸 作用下， 生成 (S)-(-)-methyl 3-oxocyclopentylacetate
  参考文献：
  名称：

  Absolute configuration of endo-cis-bicyclo[3.3.0]oct-7-en-2-ol and specific rotation of 3-oxocyclopentaneacetic acid

  摘要：

  DOI：

  10.1021/jo01317a034
• 作为产物：
  描述：

  (1R,2S,3R)-3-Hydroxy-2-(methoxycarbonyl)cyclopentanessigsaeure-methylester 在 chromium(VI) oxide 、 盐酸 、 硫酸 作用下， 以 丙酮 为溶剂， 生成 (1S)-3-氧代-环戊烷乙酸
  参考文献：
  名称：

  Absolute configuration of endo-cis-bicyclo[3.3.0]oct-7-en-2-ol and specific rotation of 3-oxocyclopentaneacetic acid

  摘要：

  DOI：

  10.1021/jo01317a034

文献信息

• Enantioselective conjugate additions of silylketene acetals to 2-carboxycyclopentenones promoted by chiral Ti complexes
  作者：Anna Bernardi、Katia Karamfilova、Silvia Sanguinetti、Carlo Scolastico

  DOI：10.1016/s0040-4020(97)00825-9

  日期：1997.9

  The conjugate addition of silylketeneacetals to 2-carbalkoxycyclopentenones 1 promoted by TADDOL . TiCl2 complexes was studied. The reactions are highly syn selective. The enantioselectivity depends on the size of the substrate ester group, with the methyl ester 1b being more enantioselective than the ethyl ester 1a. E.c. up to 47% are achieved. The absolute configuration of the major product was established by chemical correlation to the known (+)-isodchydroiridodiol. The reaction of representative doubly activated alkenes was studied: good results were obtained with cyclopentenones and gamma-butenolides. (C) 1997 Published by Elsevier Science Ltd.
• Catalytic enantioselective [2+2]-cycloaddition reaction of 2-methoxycarbonyl-2-cyclopenten-1-one by chiral copper catalyst
  作者：Yosuke Takenaka、Hisanaka Ito、Mineki Hasegawa、Kazuo Iguchi

  DOI：10.1016/j.tet.2006.01.050

  日期：2006.4

  A new catalytic system for enantioselective [2+2]-cycloaddition reaction of 2-methoxycarbonyl-2-cyclopenten-1-one with thioacetylene derivatives is described. The use of a catalytic amount (20-30 mol%) of copper(II) salt with chiral bis-pyridine ligand was found to be effective in promoting the [2 + 2]-cycloaddition reaction, furnishing the corresponding bicyclic compound in good yield and good enantioselectivity. (c) 2006 Elsevier Ltd. All rights reserved.
• An Asymmetric Enzyme-Catalyzed Retro-Claisen Reaction for the Desymmetrization of Cyclicβ-Diketones
  作者：Gideon Grogan、Jürgen Graf、Aileen Jones、Simon Parsons、Nicholas J. Turner、Sabine L. Flitsch

  DOI：10.1002/1521-3773(20010316)40:6<1111::aid-anie11110>3.0.co;2-2

  日期：2001.3.16
• HUA D. H.; VENKATARAMAN S.; COULTER M. J.; SINAI-ZINGDE G., J. ORG. CHEM., 52,(1987) N 5, 719-728
  作者：HUA D. H.、 VENKATARAMAN S.、 COULTER M. J.、 SINAI-ZINGDE G.

  DOI：——

  日期：——
• Absolute configuration of endo-cis-bicyclo[3.3.0]oct-7-en-2-ol and specific rotation of 3-oxocyclopentaneacetic acid
  作者：Hiroko Kuritani、Yoshiko Takaoka、Keiji Shingu

  DOI：10.1021/jo01317a034

  日期：1979.2