2-chloro-4-methyl-pent-2-enoic acid methyl ester | 123488-97-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-chloro-4-methyl-pent-2-enoic acid methyl ester
• 英文别名: (Z)-methyl 2-chloro-4-methylpent-2-enoate；methyl (Z)-2-chloro-4-methylpent-2-enoate
• CAS: 123488-97-1
• 化学式: C₇H₁₁ClO₂
• 分子量: 162.616
• InChiKey: IPQKICNPACXGOZ-XQRVVYSFSA-N

物化性质

• 沸点：
  189.3±13.0 °C(Predicted)
• 密度：
  1.064±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-chloro-4-methyl-pent-2-enoic acid methyl ester 以 水 为溶剂， 反应 77.0h， 以19%的产率得到(S)-methyl 2-chloro-4-methylpentanoate
  参考文献：
  名称：

  Asymmetric reduction of the prochiral carbon-carbon double bond of methyl 2-chloro-2-alkenoates by use of fermenting bakers' yeast

  摘要：

  DOI：

  10.1021/jo00282a007
• 作为产物：
  描述：

  methyl 2,2-dichloro-3-hydroxy-4-methylpentanoate 在 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以73%的产率得到2-chloro-4-methyl-pent-2-enoic acid methyl ester
  参考文献：
  名称：

  Synthesis of ( Z )-α-chloro-α,β-unsaturated esters with complete stereoselectivity promoted by samarium diiodide

  摘要：

  Stereoselective beta-elimination in alpha,alpha-dichloro-beta-hydroxyesters 2 was achieved by using samarium diiodide, yielding (Z)-alpha-chloro-alpha, beta-unsaturated esters 1. The starting compounds 2 were easily prepared by reaction of the lithium enolate of ethyl dichloroacetate with different aldehydes at -78 degreesC. A mechanism to explain this process is proposed. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.04.101

文献信息

• Enantioselective CC bond reduction of unsaturated α-chloro esters by old yellow enzymes
  作者：Elisabetta Brenna、Giovanni Fronza、Claudio Fuganti、Daniela Monti、Fabio Parmeggiani

  DOI：10.1016/j.molcatb.2011.07.008

  日期：2011.7

  The reduction of the C=Cdouble bond of some unsaturated alpha-chloro esters was investigated by means of cloned and overexpressed enoate reductases. The results were compared with those obtained by employing baker's yeast whole cells. The anti stereochemistry of hydrogen additions was confirmed by deuterium labeling experiments. (C) 2011 Elsevier B.V. All rights reserved.
• UTAKA, MASANORI;KONISHI, SATOSHI;MIZUOKA, AMI;OHKUBO, TOSHIYASU;SAKAI, TA+, J. ORG. CHEM., 54,(1989) N1, C. 4989-4992
  作者：UTAKA, MASANORI、KONISHI, SATOSHI、MIZUOKA, AMI、OHKUBO, TOSHIYASU、SAKAI, TA+

  DOI：——

  日期：——