5-deuterio-3-phenylisothiazole | 10514-30-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-deuterio-3-phenylisothiazole
• 英文别名: 5-deutero-3-phenylisothiazole；5-Deuterio-3-phenylisothiazol；3-Phenyl-5-deuterioisothiazol；5-deuterio-3-phenyl-1,2-thiazole
• CAS: 10514-30-4
• 化学式: C₉H₇NS
• 分子量: 162.219
• InChiKey: QTRJTMPLVIRDHO-WHRKIXHSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.81
• 重原子数：
  11.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.89
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  5-deuterio-3-phenylisothiazole 以 苯 为溶剂， 生成 2-deutero-4-phenylthiazole
  参考文献：
  名称：

  3-和5-苯基异噻唑的光化学。竞争的光转座途径。

  摘要：

  5-苯基异噻唑通过光环闭合-杂原子迁移途径和N（2）-C（3）互换反应途径经历光变位。通过向反应介质中添加三乙胺（TEA）并通过增加溶剂的极性来增强后一种途径。除了光转移之外，5-苯基异噻唑还经历光裂解成2-氰基-1-苯基乙硫醇，该2-氰基-1-苯基乙硫醇通过与苄基溴反应而被捕获，从而产生2-氰基-1-苯基乙-1-基苄基硫醚。3-苯基异噻唑也通过两个反应途径进行光转位，但是产物的分布不受添加TEA或改变溶剂极性的影响。

  DOI：

  10.1021/jo991785y
• 作为产物：
  描述：

  3-phenylisothiazole 在 sodium 作用下， 以 氘代甲醇-d 为溶剂， 反应 120.0h， 以88%的产率得到5-deuterio-3-phenylisothiazole
  参考文献：
  名称：

  3-和5-苯基异噻唑的光化学。竞争的光转座途径。

  摘要：

  5-苯基异噻唑通过光环闭合-杂原子迁移途径和N（2）-C（3）互换反应途径经历光变位。通过向反应介质中添加三乙胺（TEA）并通过增加溶剂的极性来增强后一种途径。除了光转移之外，5-苯基异噻唑还经历光裂解成2-氰基-1-苯基乙硫醇，该2-氰基-1-苯基乙硫醇通过与苄基溴反应而被捕获，从而产生2-氰基-1-苯基乙-1-基苄基硫醚。3-苯基异噻唑也通过两个反应途径进行光转位，但是产物的分布不受添加TEA或改变溶剂极性的影响。

  DOI：

  10.1021/jo991785y

文献信息

• Phototransposition Chemistry of Phenylisothiazoles and Phenylthiazoles. 1. Interconversions in Benzene Solution
  作者：James W. Pavlik、Pakamas Tongcharoensirikul、Nigel P. Bird、A. Colin Day、John A. Barltrop

  DOI：10.1021/ja00085a008

  日期：1994.3

  Phenylthiazoles 1-3 and phenylisothiazoles 4-6 undergo phototransposition in benzene solvent mainly by P5, P6, and P7 permutation pathways. Phenylisothiazoles 5 and 6 also transpose via a P4 permutation process to yield phenylthiazoles 2 and 3 in less than 1% yield. In benzene saturated with D2O, 2-phenylthiazole(1) and 5-phenylisothiazole (6) each phototranspose to yield 4-deuterio-3-phenylisothiazole (4-D-4) and 4-phenylthiazole (2) without deuterium incorporation. Irradiation of 4-phenylthiazole (2) under these conditions results in rapid photodeuteration to yield 2-deuterio-4-phenylthiazole (2-D-2), which subsequently phototransposes to 5-deuterio-3-phenylisothiazole (5-D-3). These experimental results can be rationalized by a mechanism involving initial electrocyclic ring closure and sigmatropic shift of sulfur around the four sides of the azetine ring. Rearomatization of each bicyclic intermediate thus allows sulfur to insert into each position in the carbon-nitrogen sequence. As a consequence, these compounds divide into a tetrad in which isomers 1, 2, 4, and 6 interconvert mainly via Ps, P6, and P7 pathways and a dyad of two compounds in which 3 phototransposes to 5 via P5 and P7 pathways. Within the tetrad, BC-6, the bicyclic intermediate derived from 5-phenylisothiazoles (6), is postulated to undergo deuteration with simultaneous sigmatropic shift of sulfur when the reaction is carried out in benzene-D2O. This mechanistic view provides one coherent interpretation for the observed phototransposition and photodeuteration reactions.
• Photochemistry of 3- and 5-Phenylisothiazoles. Competing Phototransposition Pathways
  作者：James W. Pavlik、Pakamas Tongcharoensirikul

  DOI：10.1021/jo991785y

  日期：2000.6.1

  5-Phenylisothiazole undergoes phototransposition via the electrocyclic ring closure-heteroatom migration pathway and by the N(2)-C(3) interchange reaction pathway. The latter route is enhanced by the addition of triethylamine (TEA) to the reaction medium and by increasing the polarity of the solvent. In addition to phototransposition, 5-phenylisothiazole also undergoes photocleavage to 2-cyano-1-phenylethenethiol

  5-苯基异噻唑通过光环闭合-杂原子迁移途径和N（2）-C（3）互换反应途径经历光变位。通过向反应介质中添加三乙胺（TEA）并通过增加溶剂的极性来增强后一种途径。除了光转移之外，5-苯基异噻唑还经历光裂解成2-氰基-1-苯基乙硫醇，该2-氰基-1-苯基乙硫醇通过与苄基溴反应而被捕获，从而产生2-氰基-1-苯基乙-1-基苄基硫醚。3-苯基异噻唑也通过两个反应途径进行光转位，但是产物的分布不受添加TEA或改变溶剂极性的影响。