2-(3-bromobut-3-enyl)-4-methylenethietane | 1041308-02-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二硫杂环戊烷
• 英文名称: 2-(3-bromobut-3-enyl)-4-methylenethietane
• 英文别名: 2-(3-Bromobut-3-enyl)-4-methylidenethietane
• CAS: 1041308-02-4
• 化学式: C₈H₁₁BrS
• 分子量: 219.145
• InChiKey: ZSRKMYBKQOTJOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2,7-Dibromoocta-1,7-diene-4-thiol 在 copper(l) iodide 、 potassium phosphate monohydrate 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以68%的产率得到2-(3-bromobut-3-enyl)-4-methylenethietane
  参考文献：
  名称：

  “Ligand-Free” CuI-Catalyzed Highly Efficient Intramolecular S-Vinylation of Thiols with Vinyl Chlorides and Bromides

  摘要：

  With CuI as the catalyst and K3PO4 center dot 3H(2)O as the base, highly efficient intramolecular S-vinylation of thiols with vinyl chlorides or bromides was successfully implemented without the help of an additional ligand. Moreover, the competition experiments revealed that the 4-exo cyclization is fundamentally preferred over other modes (5-exo, 6-exo, and 6-endo) of cyclization.

  DOI：

  10.1021/jo802235e

文献信息

• Nucleophilic substitution at an sp2 carbon of vinyl halides with an intramolecular thiolate moiety: synthesis of 2-alkylidenethietanes
  作者：Mao-Yi Lei、Koji Fukamizu、Yong-Jun Xiao、Wei-Min Liu、Scott Twiddy、Shunsuke Chiba、Kaori Ando、Koichi Narasaka

  DOI：10.1016/j.tetlet.2008.04.127

  日期：2008.6

  Various 2-alkylidenethietanes were synthesized by intramolecular nucleophilic substitution reactions at an sp2 carbon of vinyl halides with thiolate moieties. The reaction pathway of the substitution reactions was confirmed as a very rare SNVπ mechanism by theoretical and experimental studies.

  通过分子内的亲核取代反应，在卤代乙烯的sp 2碳上具有硫醇盐部分，合成了各种2-烷基亚乙基庚烷。的取代反应的反应路径被确认为一种非常罕见的小号Ñ通过理论和实验研究Vπ机制。
• Nucleophilic substitution reaction at an sp2 carbon of vinyl halides with an intramolecular thiol moiety: synthesis of thio-heterocycles
  作者：Mao-Yi Lei、Yong-Jun Xiao、Wei-Min Liu、Koji Fukamizu、Shunsuke Chiba、Kaori Ando、Koichi Narasaka

  DOI：10.1016/j.tet.2009.06.078

  日期：2009.8

  This article presents a full account of intramolecular vinylic substitution reactions of bromoalkenes having an acetylthio moiety, which give sulfur-containing heterocycles such as dihydrothiophene, tetrahydrothiopyran, and 2-alkylidenethietane derivatives. The reaction pathways of the substitution reactions were investigated by theoretical and experimental studies.

  本文全面介绍了具有乙酰硫基部分的溴代烯烃的分子内乙烯基取代反应，该反应可生成含硫杂环，如二氢噻吩，四氢噻喃和2-烷基亚乙基庚烷衍生物。通过理论和实验研究了取代反应的反应途径。