3-chloropropyl isopropyl sulfide | 111437-31-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-chloropropyl isopropyl sulfide
• 英文别名: 1-chloro-3-isopropylthiopropane；1-Chloro-3-[(propan-2-yl)sulfanyl]propane；1-chloro-3-propan-2-ylsulfanylpropane
• CAS: 111437-31-1
• 化学式: C₆H₁₃ClS
• 分子量: 152.688
• InChiKey: QFSNHNGOOIYVQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  8
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-chloropropyl isopropyl sulfide 在 2,6-二叔丁基吡啶 、 tert-butylammonium hexafluorophosphate(V) 作用下， 以 水 、 乙腈 为溶剂， 反应 12.0h， 以80%的产率得到1-chloro-3-i-propylsulfonylpropane
  参考文献：
  名称：

  Aced, Ahmed; Anklam, Elke; Asmus, Klaus-Dieter, Phosphorus, Sulfur and Silicon and the Related Elements, 1990, vol. 48, # 1-4, p. 53 - 62

  摘要：

  DOI：
• 作为产物：
  描述：

  异丙硫醇 、 1-溴-3-氯丙烷 在 sodium hydroxide 作用下， 以 水 为溶剂， 以64%的产率得到3-chloropropyl isopropyl sulfide
  参考文献：
  名称：

  Organic sulfur mechanisms. 36. Cyclopropanesulfonyl chloride: its mechanisms of hydrolysis and reactions with tertiary amines in organic media

  摘要：

  Cyclopropanesulfonyl chloride (1) has been synthesized and its reactions examined to see if the three-membered ring leads to unusual reactions in either 1 or the corresponding sulfene, cyclopropanethione S,S-dioxide (2). pH-rate profiles, primary kinetic isotope effects (KIE's), and pH-product ratio experiments are in full agreement with mechanisms of hydrolysis of 1 like those of a simple alkanesulfonyl chlorides (J. Am. Chem. Soc. 1992,114,1743-1749), specifically, (a) below pH 7.2 by S(N)2-S reaction with water and (b) above pH 7.3, elimination by hydroxide to form the sulfene (2) which is trapped by (i) water below pH 12.0 and (ii) hydroxide above pH 12.0. The products of the reaction of cyclopropanesulfonyl-1-d chloride (9) with triethylamine and 2-propanol in dichloromethane indicate that most of the reaction goes via 2; the analogous reaction with trimethylamine apparently proceeds by a direct formation of the sulfonylammonium chloride (14) which then yields the alpha-deuterated N,N-dimethyl sulfonamide (12, R = Me). The evident sulfene formation processes in the reaction of triethylamine with ethanesulfonyl, 2-propanesulfonyl, and cyclopropanesulfonyl chlorides show very low primary KIE's (<1.5), pointing to highly product-like transition states. Reaction of 1 with an enamine (1-pyrrolidino-2-methylpropene, 20) in the presence of a base in either water or dichloromethane gave cyclopropanesulfonpyrrolidide (23) and an aldehyde adduct (24), but no four-membered cycloadduct (21).

  DOI：

  10.1021/jo00057a027

文献信息

• Aced, Ahmed; Anklam, Elke; Asmus, Klaus-Dieter, Phosphorus, Sulfur and Silicon and the Related Elements, 1990, vol. 48, # 1-4, p. 53 - 62
  作者：Aced, Ahmed、Anklam, Elke、Asmus, Klaus-Dieter、Pohl, Klaus、Glass, Richard S.、et al.

  DOI：——

  日期：——
• Improved general method of ortho alkylation of phenols using alkyl isopropyl sulfide, sulfuryl chloride, and triethylamine. An expedient synthesis of representative oxygen heterocycles and (2R,4'R,8'R)-.alpha.-tocopherol
  作者：Seiichi Inoue、Hiroshi Ikeda、Shuichi Sato、Kiyohiro Horie、Tomomi Ota、Osamu Miyamoto、Kikumasa Sato

  DOI：10.1021/jo00233a047

  日期：1987.11
• INOUE, SEIICHI;IKEDA, HIROSHI;SATO, SHUICHI SATO, J. ORG. CHEM., 52,(1987) N 24, 5495-5497
  作者：INOUE, SEIICHI、IKEDA, HIROSHI、SATO, SHUICHI SATO

  DOI：——

  日期：——
• Organic sulfur mechanisms. 36. Cyclopropanesulfonyl chloride: its mechanisms of hydrolysis and reactions with tertiary amines in organic media
  作者：James F. King、Joe Y. L. Lam、Gabriele Ferrazzi

  DOI：10.1021/jo00057a027

  日期：1993.2

  Cyclopropanesulfonyl chloride (1) has been synthesized and its reactions examined to see if the three-membered ring leads to unusual reactions in either 1 or the corresponding sulfene, cyclopropanethione S,S-dioxide (2). pH-rate profiles, primary kinetic isotope effects (KIE's), and pH-product ratio experiments are in full agreement with mechanisms of hydrolysis of 1 like those of a simple alkanesulfonyl chlorides (J. Am. Chem. Soc. 1992,114,1743-1749), specifically, (a) below pH 7.2 by S(N)2-S reaction with water and (b) above pH 7.3, elimination by hydroxide to form the sulfene (2) which is trapped by (i) water below pH 12.0 and (ii) hydroxide above pH 12.0. The products of the reaction of cyclopropanesulfonyl-1-d chloride (9) with triethylamine and 2-propanol in dichloromethane indicate that most of the reaction goes via 2; the analogous reaction with trimethylamine apparently proceeds by a direct formation of the sulfonylammonium chloride (14) which then yields the alpha-deuterated N,N-dimethyl sulfonamide (12, R = Me). The evident sulfene formation processes in the reaction of triethylamine with ethanesulfonyl, 2-propanesulfonyl, and cyclopropanesulfonyl chlorides show very low primary KIE's (<1.5), pointing to highly product-like transition states. Reaction of 1 with an enamine (1-pyrrolidino-2-methylpropene, 20) in the presence of a base in either water or dichloromethane gave cyclopropanesulfonpyrrolidide (23) and an aldehyde adduct (24), but no four-membered cycloadduct (21).