(Z)-hex-3-ene-1,6-dithiol | 901772-75-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醇
• 英文名称: (Z)-hex-3-ene-1,6-dithiol
• 英文别名: hex-3-ene-1,6-dithiol
• CAS: 901772-75-6
• 化学式: C₆H₁₂S₂
• 分子量: 148.293
• InChiKey: VNBMVCXNRYRELR-UPHRSURJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  8
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-hex-3-ene-1,6-dithiol 在 氧气 、 cesium fluoride 作用下， 以 乙腈 为溶剂， 以65%的产率得到(Z)-3,4,7,8-tetrahydro-1,2-dithiocine
  参考文献：
  名称：

  Synthesis and properties of disulfide-bond containing eight-membered rings

  摘要：

  The cyclocystine ring structure (CRS, 3), which results from a disulfide-bond between adjacent cysteine residues, is a rare motif in protein structures and is functionally important to those few proteins that posses it. This letter will focus on the construction of CRS mimics and the determination of their respective redox potentials. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.04.023
• 作为产物：
  描述：

  (Z)-hex-3-ene-1,6-diol 在 potassium carbonate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 甲醇 、 乙醚 为溶剂， 生成 (Z)-hex-3-ene-1,6-dithiol
  参考文献：
  名称：

  Synthesis and properties of disulfide-bond containing eight-membered rings

  摘要：

  The cyclocystine ring structure (CRS, 3), which results from a disulfide-bond between adjacent cysteine residues, is a rare motif in protein structures and is functionally important to those few proteins that posses it. This letter will focus on the construction of CRS mimics and the determination of their respective redox potentials. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.04.023

文献信息

• Thia-Prins Bicyclization Approach for the Stereoselective Synthesis of Dithia- and Azathia-Bicycles
  作者：B. V. Subba Reddy、A. Venkateswarlu、Prashant Borkar、J. S. Yadav、M. Kanakaraju、A. C. Kunwar、B. Sridhar

  DOI：10.1021/jo400680w

  日期：2013.6.21

  A novel thia-Prins bicyclization approach has been developed for the first time for the synthesis of hexahydro-2H-thieno[3,2-c]thiopyran derivatives from the coupling of homoallylic mercaptans such as hex-3-ene-1,6-dithiol with various aldehydes using 10 mol % InBr3 in dichloromethane with high selectivity. In addition, the coupling of (E)-N-(6-mercaptohex-3-enyl)-4-methylbenzenesulfonamide with aldedydes

  首次开发了一种新颖的thia-Prins双环化方法，用于通过均质硫醇（如hex-3-ene-1,6）的偶合反应合成六氢-2 H-噻吩并[3,2- c ]硫代吡喃衍生物。在二氯甲烷中使用10 mol％InBr 3具有高选择性的-二硫醇与各种醛。另外，（E）-N-（6-巯基己基-3-烯基）-4-甲基苯磺酰胺与醛类的偶联以良好的产率提供了相应的N-甲苯磺酰基氢硫代吡喃并[4，3- b ]吡咯衍生物。这反应是立体选择性得到反式从-融合产品Ë -homoallyllic硫醇和Z-均烯丙基硫醇的顺式融合产物。
• Synthesis, redox properties, and conformational analysis of vicinal disulfide ring mimics
  作者：Erik L. Ruggles、P. Bruce Deker、Robert J. Hondal

  DOI：10.1016/j.tet.2008.11.085

  日期：2009.2

  A vicinal disulfide ring (VDR) results from disulfide-bond formation between two adjacent cysteine residues. This eight-membered ring is a rare motif in protein structures and is functionally important to those few proteins that posses it. This article focuses on the construction of strained and unstrained VDR mimics, discernment of the preferred conformation of these mimics, and the determination of their respective disulfide redox potentials. (C) 2008 Elsevier Ltd. All rights reserved.