2,2-dichloro-3,3,3-trifluoro-1-phenylpropyl methanesulfonate | 107686-45-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,2-dichloro-3,3,3-trifluoro-1-phenylpropyl methanesulfonate
• 英文别名: (2,2-Dichloro-3,3,3-trifluoro-1-phenylpropyl) methanesulfonate
• CAS: 107686-45-3
• 化学式: C₁₀H₉Cl₂F₃O₃S
• 分子量: 337.147
• InChiKey: CXGYUJPQVLDSSH-UHFFFAOYSA-N

物化性质

• 沸点：
  362.4±42.0 °C(Predicted)
• 密度：
  1.514±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,2-dichloro-3,3,3-trifluoro-1-phenylpropyl methanesulfonate 在 四甲基氯化铵 作用下， 以 甲醇 为溶剂， 以51%的产率得到(3,3,3-三氟丙基)苯
  参考文献：
  名称：

  Electroreductive coupling of halofluoro compounds with aldehydes

  摘要：

  Electroreductive intermolecular coupling of halofluoro compounds such as 1,1,1-trichloro-2,2,2-trifluoroethane, methyl chlorodifluoroacetate, and perfluoroalkyl halides with aldehydes took place effectively in the presence of chlorotrimethylsilane and one of the coupling products, 2,2-dichloro-3,3,3-trifluoro-1-phenyl-1-propanol, was selectively convertible to a variety of compounds with using the electroreduction as a key reaction.

  DOI：

  10.1016/0040-4039(91)80223-s
• 作为产物：
  描述：

  苯甲醛 在 三甲基氯硅烷 、 四乙基对甲苯磺酸铵 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 2,2-dichloro-3,3,3-trifluoro-1-phenylpropyl methanesulfonate
  参考文献：
  名称：

  Electroreductive coupling of halofluoro compounds with aldehydes

  摘要：

  Electroreductive intermolecular coupling of halofluoro compounds such as 1,1,1-trichloro-2,2,2-trifluoroethane, methyl chlorodifluoroacetate, and perfluoroalkyl halides with aldehydes took place effectively in the presence of chlorotrimethylsilane and one of the coupling products, 2,2-dichloro-3,3,3-trifluoro-1-phenyl-1-propanol, was selectively convertible to a variety of compounds with using the electroreduction as a key reaction.

  DOI：

  10.1016/0040-4039(91)80223-s

文献信息

• Practical, Stereocontrolled Synthesis of Polyfluorinated Artificial Pyrethroids
  作者：Makoto Fujita、Kiyosi Kondo、Tamejiro Hiyama

  DOI：10.1246/bcsj.60.4385

  日期：1987.12

  Practical and stereocontrolled approaches to polyfluorinated synthetic pyrethroids based on aldehyde addition of CF3CCl2ZnCl are described. The zinc reagent was allowed to react with 3-formyl-2,2-dimethylcyclopropanecarboxylates (6) to give the corresponding adducts. These were acetylated and then reduced again with zinc to afford (1R*, 3S*)-3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylates (12). The (1R*, 3R*)-isomer was derived from 2,2-dichloro-1,1,1-trifluoro-5-methyl-4-hexen-3-ol by diazoacetylation, Cu(II)-catalyzed intramolecular carbene addition, and finally by the zinc reduction. An alternative access to 12 and its halogen homologues of the (Z)-pyrethroids involves addition of 1-halo-2,2-difluoroethenyl group across the CHO group of 6 and subsequent regio- and stereoselective halogenation.

  本文介绍了基于 CF3CCl2ZnCl 的醛加成法制备多氟合成拟除虫菊酯的实用立体控制方法。锌试剂可与 3-甲酰基-2,2-二甲基环丙烷羧酸盐 (6) 反应，生成相应的加合物。这些加合物经乙酰化后再次用锌还原，得到 (1R*，3S*)-3-(2-氯-3,3,3-三氟-1-丙烯基)-2,2-二甲基环丙烷羧酸盐 (12)。(1R*, 3R*)异构体是由 2,2-二氯-1,1,1-三氟-5-甲基-4-己烯-3-醇通过重氮乙酰化、Cu(II)催化的分子内碳烯加成，最后通过锌还原得到的。获得 12 及其 (Z)- 吡咯烷卤素同系物的另一种方法是在 6 的 CHO 基上添加 1-卤代-2,2-二氟乙烯基，然后进行区域和立体选择性卤化。
• Practical and stereocontrolled syntheses of both (1R★,3S★)- and (1R★,3R★)-3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylates
  作者：Makoto Fujita、Tamejiro Hiyama、Kiyosi Kondo

  DOI：10.1016/s0040-4039(00)84469-x

  日期：1986.1
• FUJITA, MAKOTO;KONDO, KIYOSI;HIYAMA, TAMEJIRO, BULL. CHEM. SOC. JAP., 60,(1987) N 12, 4385-4394
  作者：FUJITA, MAKOTO、KONDO, KIYOSI、HIYAMA, TAMEJIRO

  DOI：——

  日期：——
• Electroreductive coupling of halofluoro compounds with aldehydes
  作者：Tatsuya Shono、Naoki Kise、Hideaki Oka

  DOI：10.1016/0040-4039(91)80223-s

  日期：1991.11

  Electroreductive intermolecular coupling of halofluoro compounds such as 1,1,1-trichloro-2,2,2-trifluoroethane, methyl chlorodifluoroacetate, and perfluoroalkyl halides with aldehydes took place effectively in the presence of chlorotrimethylsilane and one of the coupling products, 2,2-dichloro-3,3,3-trifluoro-1-phenyl-1-propanol, was selectively convertible to a variety of compounds with using the electroreduction as a key reaction.