2-(三氯甲基)-1,3-二噻戊环 | 5616-59-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二硫杂环戊烷
• 中文名称: 2-(三氯甲基)-1,3-二噻戊环
• 英文名称: 2-(trichloromethyl)-1,3-dithiolane
• 英文别名: 2-(trichlormethyl)-1,3-dithiolan
• CAS: 5616-59-1
• 化学式: C₄H₅Cl₃S₂
• 分子量: 223.575
• InChiKey: PIRSHZAISZDDCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(三氯甲基)-1,3-二噻戊环 在 双氧水 、 vanadia 作用下， 以 叔丁醇 为溶剂， 反应 1.0h， 以87%的产率得到2-(trichloromethyl)-1,3-dithiolane S-oxide
  参考文献：
  名称：

  One-Pot Synthesis of 4,5-Unsubstituted 1,3-Dithioles and 2-Alkylidene-1,3-dithioles from 1,3-DithiolaneS-Oxides

  摘要：

  报告中介绍了通过碘三甲基硅烷和二异丙基乙胺（许尼格碱）对相应的 1,3-二硫环戊烷 S-氧化物进行形式脱水，从而高效合成标题化合物的方法。

  DOI：

  10.1055/s-1990-26849
• 作为产物：
  描述：

  1,2-乙二硫醇 、 三氯乙醛 在 三氟化硼乙醚 作用下， 以 氯仿 为溶剂， 反应 48.0h， 以85%的产率得到2-(三氯甲基)-1,3-二噻戊环
  参考文献：
  名称：

  A variable mechanism for the nucleophilic vinylic substitutions in a series of gem-dihalogenated alkenes by a bidentate sulfur nucleophile: an experimental and AM1 theoretical study

  摘要：

  The nucleophilic substitutions of a series of gem-dihalogenated alkenes 3,5,7,8, and 9 (RS)2C=CX2 (X = Cl, F) with 1,2-benzenedithiolate b have been studied. Depending on the structures of the R groups (alkyl, saturated and unsaturated cycloalkyls, aromatic ring), the course of the reactions and the structures of the yielded products are modified. In the frame of the addition-elimination-type mechanism for these nucleophilic substitutions, the energy contents of the anionic intermediates, resulting from the additions of the nucleophile b to the unsaturated centers, is calculated at the AM1 method level. For the compounds 5, 7, 8, and 9, the calculated energies nicely corroborate the experimental results. For 3, anionic intermediates are no longer found by calculation, and a synchronous single-step substitution is strongly suggested.

  DOI：

  10.1021/jo00069a035

文献信息

• Schaumann, Ernst; Scheiblich, Stefan; Wriede, Ulrich, Chemische Berichte, 1988, vol. 121, p. 1165 - 1176
  作者：Schaumann, Ernst、Scheiblich, Stefan、Wriede, Ulrich、Adiwidjaja, Gunadi

  DOI：——

  日期：——
• Generation of thioketenes via cycloreversion of 1,3-dithiolane-derived sulfur ylides
  作者：Ernst Schaumann、Stefan Scheiblich

  DOI：10.1016/s0040-4039(00)95012-3

  日期：1985.1
• SCHAUMANN, ERNST;SCHEIBLICH, STEFAN;WRIEDE, ULRICH;ADIWIDJAJA, GUNADI, CHEM. BER., 121,(1988) N 6, 1165-1175
  作者：SCHAUMANN, ERNST、SCHEIBLICH, STEFAN、WRIEDE, ULRICH、ADIWIDJAJA, GUNADI

  DOI：——

  日期：——
• A variable mechanism for the nucleophilic vinylic substitutions in a series of gem-dihalogenated alkenes by a bidentate sulfur nucleophile: an experimental and AM1 theoretical study
  作者：Yves Gimbert、Alec Moradpour、Georges Dive、Dominique Dehareng、Khaled Lahlil

  DOI：10.1021/jo00069a035

  日期：1993.8

  The nucleophilic substitutions of a series of gem-dihalogenated alkenes 3,5,7,8, and 9 (RS)2C=CX2 (X = Cl, F) with 1,2-benzenedithiolate b have been studied. Depending on the structures of the R groups (alkyl, saturated and unsaturated cycloalkyls, aromatic ring), the course of the reactions and the structures of the yielded products are modified. In the frame of the addition-elimination-type mechanism for these nucleophilic substitutions, the energy contents of the anionic intermediates, resulting from the additions of the nucleophile b to the unsaturated centers, is calculated at the AM1 method level. For the compounds 5, 7, 8, and 9, the calculated energies nicely corroborate the experimental results. For 3, anionic intermediates are no longer found by calculation, and a synchronous single-step substitution is strongly suggested.
• One-Pot Synthesis of 4,5-Unsubstituted 1,3-Dithioles and 2-Alkylidene-1,3-dithioles from 1,3-Dithiolane<i>S</i>-Oxides
  作者：Ernst Schaumann、Susanne Winter-Extra、Knut Kummert、Stefan Scheiblich

  DOI：10.1055/s-1990-26849

  日期：——

  An efficient synthesis of the title compounds via formal dehydration of the corresponding 1,3-dithiolane S-oxides with iodotrimethylsilane and diisopropylethylamine (Hünig's base) is reported.

  报告中介绍了通过碘三甲基硅烷和二异丙基乙胺（许尼格碱）对相应的 1,3-二硫环戊烷 S-氧化物进行形式脱水，从而高效合成标题化合物的方法。