1-chloro-3-(4-chlorophenylsulfanyl)propan-2-one | 946528-39-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-chloro-3-(4-chlorophenylsulfanyl)propan-2-one
• 英文别名: 1-chloro-3-[(4-chlorophenyl)sulfanyl]acetone；1-Chloro-3-(4-chlorophenyl)sulfanylpropan-2-one
• CAS: 946528-39-8
• 化学式: C₉H₈Cl₂OS
• 分子量: 235.134
• InChiKey: GLAMHWGMGLSTLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-chloro-3-(4-chlorophenylsulfanyl)propan-2-one 在 Saccharomyces cerevisiae yeast 作用下， 以 乙醇 、 水 为溶剂， 反应 26.0h， 生成 (S)-(+)-2-((4-chlorophenylsulfanyl)methyl)thiirane
  参考文献：
  名称：

  Asymmetric reduction of α-thiocyanatoketones by Saccharomyces cerevisiae and Mortierella isabellina—a new route to optically active thiiranes

  摘要：

  A simple method for the preparation of optically active 1-aryloxy- and 1-arylsulphanyl-3-thiocyanatopropan-2-oles from racemic 1-chloro-3-aryloxy- and 1-chloro-3-arylsulphanyl-2-propanols via 1-aryloxy- and 1-arylsulphanyl-3-thiocyanatopropan-2-ones has been developed. The enantiomerically enriched beta-hydroxythiocyanates were obtained by a microbiological reduction of the thiocyanatoketones with Saccharomyces cerevisiae or Mortierella isabellina and subsequently converted into optically active thiiranes on treatment with a lithium hydroxide solution. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.04.023
• 作为产物：
  描述：

  1,3-二氯丙酮 、 4-氯苯硫酚 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 17.0h， 以61%的产率得到1-chloro-3-(4-chlorophenylsulfanyl)propan-2-one
  参考文献：
  名称：

  Asymmetric reduction of α-thiocyanatoketones by Saccharomyces cerevisiae and Mortierella isabellina—a new route to optically active thiiranes

  摘要：

  A simple method for the preparation of optically active 1-aryloxy- and 1-arylsulphanyl-3-thiocyanatopropan-2-oles from racemic 1-chloro-3-aryloxy- and 1-chloro-3-arylsulphanyl-2-propanols via 1-aryloxy- and 1-arylsulphanyl-3-thiocyanatopropan-2-ones has been developed. The enantiomerically enriched beta-hydroxythiocyanates were obtained by a microbiological reduction of the thiocyanatoketones with Saccharomyces cerevisiae or Mortierella isabellina and subsequently converted into optically active thiiranes on treatment with a lithium hydroxide solution. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.04.023

文献信息

• Nitroketene dithioacetal chemistry: Synthesis of 2-alkylthio-3-nitrothiophenes from nitroketene dithioacetate and chloromethyl ketones
  作者：H. Surya Prakash Rao、K. Vasantham

  DOI：10.1021/jo9008639

  日期：2009.9.4

  An effective synthesis of highly functionalized 3-nitrothiophenes was achieved from the reaction of simple, inexpensive, and readily available dipotassium 2-nitro-1,1-ethylyenedithiolate with α-chloromethyl ketones in toluene catalyzed by tetrabutylammonium bromide (TBAB). Thiophene formation is highly sensitive and selective for chlorine, present as a leaving group in α-chloromethyl ketones.

  通过简单，廉价且易于获得的2-硝基-1,1-乙基二硫代二钾二钾与α-氯甲基酮在四丁基溴化铵（TBAB）催化下的甲苯反应，可以有效合成高度官能化的3-硝基噻吩。噻吩的形成对氯非常敏感并且对氯具有选择性，氯作为α-氯甲基酮中的离去基团存在。
• Asymmetric reduction of α-thiocyanatoketones by Saccharomyces cerevisiae and Mortierella isabellina—a new route to optically active thiiranes
  作者：Edyta Łukowska、Jan Plenkiewicz

  DOI：10.1016/j.tetasy.2007.04.023

  日期：2007.6

  A simple method for the preparation of optically active 1-aryloxy- and 1-arylsulphanyl-3-thiocyanatopropan-2-oles from racemic 1-chloro-3-aryloxy- and 1-chloro-3-arylsulphanyl-2-propanols via 1-aryloxy- and 1-arylsulphanyl-3-thiocyanatopropan-2-ones has been developed. The enantiomerically enriched beta-hydroxythiocyanates were obtained by a microbiological reduction of the thiocyanatoketones with Saccharomyces cerevisiae or Mortierella isabellina and subsequently converted into optically active thiiranes on treatment with a lithium hydroxide solution. (C) 2007 Elsevier Ltd. All rights reserved.