methyl (Z)-2,4,4-trichloro-2-butenoate | 111254-13-8

• 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: methyl (Z)-2,4,4-trichloro-2-butenoate
• 英文别名: (Z)-methyl 2,4,4-trichlorobut-2-enoate；methyl (Z)-2,4,4-trichlorobut-2-enoate
• CAS: 111254-13-8
• 化学式: C₅H₅Cl₃O₂
• 分子量: 203.452
• InChiKey: WIXCRAUYVWLCJL-IHWYPQMZSA-N

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：
  0.4
• 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：

  methyl (Z)-2,4,4-trichloro-2-butenoate 在 葡萄糖 、 recombinant GDH 、 recombinant old yellow enzyme 1 、 烟酰胺腺嘌呤双核苷酸磷酸盐 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 methyl 2,4,4-trichlorobutanoate
  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
• 作为产物：
  描述：

  甲醇 、 在 硫酸 作用下， 生成 methyl (Z)-2,4,4-trichloro-2-butenoate
  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

• A facile synthesis of optically pure L-armentomycin and its D-isomer.Highly enantioselective reduction of the CC double bond of methyl (E)- and (Z)-2,4,4-trichloro-2-butenoate by using baker's yeast
  作者：Masanori Utaka、Satoshi Konishi、Toshiyasu Okubo、Sadao Tsuboi、Akira Takeda

  DOI：10.1016/s0040-4039(00)95950-1

  日期：——

  Optically pure L-armentomycin [(S)-2-amino-4,4-dichlorobutanoic acid] and its D-isomer [(R)-2-amino-4,4-dichlorobutanoic acid] were prepared by using methyl (E)- and (Z)-2,4,4-trichloro-2-butenoate as key intermediate, which were reduced with baker's yeast to (R)- and (S)-2,4,4-trichlorobutanoate in 84~92 and 97~98% ee, respectively, in 60~65% yields.

  使用甲基（E）制备光学纯的L-阿曼霉素[（S）-2-氨基-4,4-二氯丁酸]及其D-异构体[（R）-2-氨基-4,4-二氯丁酸]。-和（Z）-2,4,4-三氯-2-丁烯酸酯为关键中间体，在84〜92和97中用面包酵母还原为（R）-和（S）-2,4,4-三氯丁酸酯ee分别为〜98％ee，产率为60〜65％。
• 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
• 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：——