(1S,2S,5R)-2-[(2-isopropyl-5-methylcyclohexyl)sulfanyl]-1,3-benzothiazole

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1S,2S,5R)-2-[(2-isopropyl-5-methylcyclohexyl)sulfanyl]-1,3-benzothiazole
• 英文别名: 2-((1S,2S,5R)-2-isopropyl-5-methylcyclohexylthio)benzo[d]thiazole；2-[(1S,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]sulfanyl-1,3-benzothiazole
• 化学式: C₁₇H₂₃NS₂
• 分子量: 305.508
• InChiKey: XFYVFDNOOZFOCF-WWGRRREGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  66.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (1Alpha,2Alpha,5β)-(+-)-5-甲基 在 甲醇 、 di-(p-nitrobenzyl) azodicarboxylate 、 copper diacetate 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 为溶剂， 反应 8.2h， 生成 (1S,2S,5R)-2-[(2-isopropyl-5-methylcyclohexyl)sulfanyl]-1,3-benzothiazole
  参考文献：
  名称：

  二对硝基苄基偶氮二羧酸酯（DNAD）：Mitsunobu反应的另一种偶氮试剂

  摘要：

  分两步制备呈亮黄色固体的二对硝基苄基偶氮二羧酸酯，产率为83.6％，可以用作Mitsunobu反应中的偶氮试剂。当使用手性仲醇时，在Mitsunobu条件下发生足够的构型醇转化。由DNAD产生的肼在某些溶剂（如THF和CH 2 Cl 2）中可半溶，因此仅通过过滤即可将其轻松从反应混合物中分离出来。然后可以将回收的肼化合物重新暴露于氧化剂以产生DNAD。由于DNAD在环境温度下比DIAD更稳定并且易于分离，因此它是Mitsunobu反应的良好替代偶氮试剂。

  DOI：

  10.1016/j.tet.2010.12.036

文献信息

• Dicyclopentyl azodicarboxylate (DCpAD): A new alternative azo-reagent for the Mitsunobu reaction
  作者：Jian Hai Yang、Li Yan Dai、Xiao Zhong Wang、Ying Qi Chen

  DOI：10.1016/j.cclet.2011.03.017

  日期：2011.9

  Dicyclopentyl azodicarboxylate is introduced as a new azo-reagent which can be conveniently prepared in two steps and be used in the Mitsunobu reaction. Though there are no distinct difference of reactivity between DCpAD and DEAD, the former is a more preferable azo-reagent for its stability.

  引入偶氮二羧酸二环戊酯作为一种新型的偶氮试剂，可以方便地分两步制备并用于Mitsunobu反应。尽管DCpAD和DEAD之间没有明显的反应性差异，但是前者由于其稳定性是更优选的偶氮试剂。
• Conversion of Alcohols to Alkyl Aryl Sulfides by a New Type of Oxidation–Reduction Condensation Using Phenyl Diphenylphosphinite
  作者：Kiichi Kuroda、Yuji Maruyama、Yujiro Hayashi、Teruaki Mukaiyama

  DOI：10.1246/bcsj.82.381

  日期：2009.3.15

  Preparation of alkyl aryl sulfides from alcohols and arenethiols such as 2-sulfanyl-1,3-benzothiazole (BtzSH) is described by a new type of oxidation–reduction condensation using phenyl diphenylpho...

  从醇和芳烃硫醇如 2-硫烷基-1,3-苯并噻唑 (BtzSH) 制备烷基芳基硫化物是通过使用苯基二苯基膦的一种新型氧化还原缩合反应来描述的。
• A New Method for the Preparation of Alkyl Aryl Sulfides from Alcohols via Alkoxydiphenylphosphines by Oxidation–Reduction Condensation
  作者：Teruaki Mukaiyama、Kazuhiro Ikegai

  DOI：10.1246/cl.2004.1522

  日期：2004.11

  A new method for the preparation of alkyl aryl sulfides from alcohols via alkoxydiphenylphosphines by oxidation-reduction condensation was established. Various primary, secondary, and tertiary alcohols were successfully converted into the corresponding sulfides in moderate to high yields.

  建立了烷氧基二苯基膦氧化还原缩合醇合成烷基芳基硫化物的新方法。各种伯醇、仲醇和叔醇以中等至高产率成功转化为相应的硫化物。
• Stereospecific Synthesis of Alkyl Aryl Sulfides from Alcohols and 2-Sulfanylbenzothiazole Using Aryl Diphenylphosphinite and Azide Compounds by a New Type of Oxidation–Reduction Condensation
  作者：Kiichi Kuroda、Yuji Maruyama、Yujiro Hayashi、Teruaki Mukaiyama

  DOI：10.1246/cl.2008.836

  日期：2008.8.5

  The preparation of alkyl aryl sulfides from alcohols and 2-sulfanylbenzothiazole using phenyl diphenylphosphinite and azide compounds by a new type of oxidation–reduction condensation is described....

  描述了使用苯基二苯基次膦酸盐和叠氮化合物通过新型氧化还原缩合反应从醇和 2-硫烷基苯并噻唑制备烷基芳基硫化物。
• A New Type of Oxidation-Reduction Condensation by the Combined Use of Phenyl Diphenylphosphinite and Oxidant
  作者：Teruaki Mukaiyama、Kiichi Kuroda、Yuji Maruyama

  DOI：10.3987/rev-09-sr(s)1

  日期：——

  A new type of oxidation-reduction condensation of alcohols with sulfur, nitrogen, and oxygen nucleophiles by the combined use of phenyl diphenylphosphinite (PhOPPh2) and oxidants such as azides or diethyl azodicarboxylate (DEAD) are described. In these reactions, chiral secondary and tertiary alcohols are converted into the corresponding chiral sulfides, azides, esters and ethers under mild and neutral conditions with almost complete inversion of stereochemical configuration.