2-cyclohexen-1-yl-1-phenyl-1H-tetrazole-5-thiol | 95926-76-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-cyclohexen-1-yl-1-phenyl-1H-tetrazole-5-thiol
• 英文别名: 5-(2-Cyclohexen-1-ylthio)-1-phenyl-1H-tetrazol；5-(cyclohex-2-enylthio)-1-phenyl-1H-tetrazole；5-(2-cyclohexenylthio)-1-phenyl-1H-tetrazole；5-(2-Cyclohexenylsulfanyl)-1-phenyltetrazole；5-cyclohex-2-en-1-ylsulfanyl-1-phenyltetrazole
• CAS: 95926-76-4
• 化学式: C₁₃H₁₄N₄S
• 分子量: 258.347
• InChiKey: OCUQYKJLGRASNE-UHFFFAOYSA-N

物化性质

• 沸点：
  440.5±48.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  68.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-cyclohexen-1-yl-1-phenyl-1H-tetrazole-5-thiol 在 二(氰基苯)二氯化钯 作用下， 以 甲苯 为溶剂， 反应 96.0h， 以90%的产率得到1-(2-Cyclohexen-1-yl)-1,4-dihydro-4-phenyl-5H-tetrazol-5-thion
  参考文献：
  名称：

  Quast, Helmut; Nahr, Uwe, Chemische Berichte, 1985, vol. 118, # 2, p. 526 - 540

  摘要：

  DOI：
• 作为产物：
  描述：

  2-环己烯醇 、 1-苯基-5-巯基四氮唑 在 gallium(III) triflate 作用下， 以 二氯甲烷 为溶剂， 以91%的产率得到2-cyclohexen-1-yl-1-phenyl-1H-tetrazole-5-thiol
  参考文献：
  名称：

  Ga(OTf)₃-Catalyzed Direct Substitution of Alcohols with Sulfur Nucleophiles

  摘要：

  It is reported that Ga(OTf)(3) catalyzes the direct displacement of alcohols with sulfur nucleophiles. The products are versatile intermediates that can be utilized in carbon carbon, carbon sulfur bond formation or used in modified Julia olefination reactions. The only byproduct generated is water.

  DOI：

  10.1021/ol102565b

文献信息

• Convenient synthesis of allylic sulfides and application to allylic carbon-carbon bond formation.
  作者：Kanoko TSUBOYAMA、Kazuyoshi TAKEDA、Katsumi TORII、Haruo OGURA

  DOI：10.1248/cpb.38.2357

  日期：——

  Allylic sulfides were synthesized from allylic alcohols 1 using S, S'-bis(1-phenyl-1H-tetrazol-5-yl) dithiocarbonate (2) by means of a single-step reaction. The allylic sulfides were coupled with a Grignard reagent or carbanion in the presence of a catalytic amount of copper(I) bromide or palladium(0).

  阿利基硫化物通过一步反应，由阿利基醇1与S,S'-双(1-苯基-1H-四唑-5-基)二硫代碳酸酯2合成。这些阿利基硫化物在催化量的铜(I)溴化物或钯(0)存在下，与格氏试剂或碳负离子进行偶联反应。
• Single-step preparation of allylic sulfides having 1-phenyltetrazole-5-thio group from allylic alcohols using ,′-BIS(1-phenyl-1-tetrazol-5-YL) dithiocarbonate and reactions involving the allylic sulfides
  作者：Kazuyoshi Takeda、Kanoko Tsuboyama、Katsumi Torii、Maki Murata、Haruo Ogura

  DOI：10.1016/s0040-4039(00)80428-1

  日期：1988.1

  The reaction of allylic alcohols and ,′-bis(1-phenyl-1-tetrazol-5-yl) dithiocarbonate () gave allylic sulfides having 1-phenyltetrazole-5-thio group in a single step. Furthermore, these allylic sulfides could be applied to carbon-carbon bond and carbon-sulfur bond formations by using Grignard reagents or carbanions in the presence of a catalytic amount of copper(I)bromide or palladium (0), respectively

  烯丙醇和的反应，双（1-苯基-1-四唑-5-基）二硫代碳酸酯（），得到具有在一个单一的步骤1苯基四唑基-5-硫代基烯丙基硫化物。此外，在催化量的溴化铜（I）或钯（0）的存在下，分别使用格氏试剂或碳负离子，可以将这些烯丙基硫化物应用于碳-碳键和碳-硫键的形成。
• Direct Synthesis of Thioethers from Carboxylates and Thiols Catalyzed by FeCl₃
  作者：Kunuru Venkatesham、Chitturi Bhujanga Rao、Chanti Babu Dokuburra、Richard A. Bunce、Yenamandra Venkateswarlu

  DOI：10.1021/acs.joc.5b02143

  日期：2015.11.20

  A new and efficient method has been developed for the synthesis of thioethers from carboxylates and thiols. The reaction proceeds via a Fe(III)-catalyzed direct displacement of carboxylates from benzylic or allylic esters by heterocyclic thiols. Short reaction times, good to excellent yields of products, and few side reactions are the significant features of the new protocol.

  已经开发了一种新的有效方法，用于从羧酸盐和硫醇合成硫醚。该反应通过杂环硫醇通过Fe（III）催化的羧酸酯从苄基或烯丙基酯直接置换而进行。新协议的显着特点是反应时间短，产品收率好至极好，副反应少。
• Silver triflate-promoted coupling reactions of benzylic and allylic sulfides with -silylated enolates of ketones and esters, a synthesis of (±)--turmerone
  作者：Kazuyoshi Takeda、Katsumi Torii、Haruo Ogura

  DOI：10.1016/s0040-4039(00)94388-0

  日期：1990.1
• Alkylation of thiols with trichloroacetimidates under neutral conditions
  作者：Brian C. Duffy、Kyle T. Howard、John D. Chisholm

  DOI：10.1016/j.tetlet.2014.12.042

  日期：2015.6

  Trichloroacetimidates are displaced with thiols to form the corresponding sulfides without the need for an added acid or base by simply heating the reactants in refluxing THF. This operationally simple procedure provides the corresponding sulfides in excellent yields with only the formation of the neutral trichloroacetamide as the side product. The imidate may also be formed in situ, allowing for a direct method for the formation of sulfides from alcohols. This reaction provides a general method for the synthesis of a variety of sulfides from inexpensive and readily available alcohol starting materials. (C) 2014 Elsevier Ltd. All rights reserved.