(S)-methyl 2-chloro-4-methylpentanoate | 114438-68-5

• 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: (S)-methyl 2-chloro-4-methylpentanoate
• 英文别名: α-Chlor-isocapronsaeuremethylester；methyl (2S)-2-chloro-4-methylpentanoate
• CAS: 114438-68-5；55905-16-3；114438-67-4；114438-83-4
• 化学式: C₇H₁₃ClO₂
• 分子量: 164.632
• InChiKey: YYGYFVZQCDLIFY-LURJTMIESA-N

物化性质

• 沸点：
  40 °C(Press: 5 Torr)
• 密度：
  1.030±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：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  (S)-methyl 2-chloro-4-methylpentanoate 在 C₂₄H₃₂FeN₆⁽²⁺⁾*2F₆Sb^(1-) 、 双氧水 、 溶剂黄146 作用下， 以 氘代乙腈 、 水 为溶剂， 反应 16.2h， 以13%的产率得到(3S)-3-chloro-5,5-dimethyloxolan-2-one
  参考文献：
  名称：

  Directed Metal (Oxo) Aliphatic C–H Hydroxylations: Overriding Substrate Bias

  摘要：

  The first general strategy for a directing effect on metal (oxo)-promoted C-H hydroxylations is described. Carboxylic acid moieties on the substrate overcome unfavorable electronic, steric, and stereoelectronic biases in C-H hydroxylations catalyzed by the non-heme iron complex Fe(PDP). In a demonstration of the power of this directing effect, C-H oxidation is diverted away from an electronically favored C-1 H abstraction/rearrangement pathway in the paclitaxel framework to enable installation of C-2 oxidation in the naturally occurring oxidation state and stereoconfiguration.

  DOI：

  10.1021/ja301685r
• 作为产物：
  描述：

  ethyl (Z)-2-chloro-4-methylpent-2-enoate 在 硫酸 作用下， 以 乙醚 、 水 、 丙酮 为溶剂， 生成 (S)-methyl 2-chloro-4-methylpentanoate
  参考文献：
  名称：

  Enantioselective CC bond reduction of unsaturated α-chloro esters by old yellow enzymes

  摘要：

  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.

  DOI：

  10.1016/j.molcatb.2011.07.008

文献信息

• New assignments for circular dichroism bands of carboxylic acid derivatives
  作者：T. Połoński

  DOI：10.1016/0040-4020(75)80044-5

  日期：——

  The CD of some carboxylic acid esters has been investigated in various solvents. Two bands were found in the 200–250 nm range for all esters and also for lactone 9. The band at 230 nm depends on the nucleophilicity of the heteroatom attached to the asymmetric centre, and vanishes in acidic media. On the basis of these observations and of the solvent effect, the 230 nm band has been assigned to the

  已经在各种溶剂中研究了某些羧酸酯的CD。所有酯以及内酯9均在200–250 nm范围内发现两个谱带。230 nm处的谱带取决于连接到不对称中心的杂原子的亲核性，并在酸性介质中消失。根据这些观察结果和溶剂效应，将230 nm谱带分配给电子从杂原子的非键合轨道到羧基的π*反键合轨道的CT跃迁，以及210 nm波段到n→π*羧酸盐跃迁。
• METHOD FOR PRODUCING CARBOXYLIC ACID AND ALCOHOL BY HYDROLYSIS OF ESTER
  申请人：National University Corporation Nagoya University

  公开号：EP2799422B1

  公开（公告）日：2018-02-14
• Asymmetric reduction of the prochiral carbon-carbon double bond of methyl 2-chloro-2-alkenoates by use of fermenting bakers' yeast
  作者：Masanori Utaka、Satoshi Konishi、Ami Mizuoka、Toshiyasu Ohkubo、Takashi Sakai、Sadao Tsuboi、Akira Takeda

  DOI：10.1021/jo00282a007

  日期：1989.10
• Selective Bromination of α-Chloro and α-Bromo Carboxylic Acid Derivatives
  作者：Joanne P. Shaw、Eng Wui Tan

  DOI：10.1021/jo960311l

  日期：1996.1.1
• 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：——