[1,3]Dioxolan-2-yl-methanethiol | 5694-66-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧戊环
• 英文名称: [1,3]Dioxolan-2-yl-methanethiol
• 英文别名: (1,3-Dioxolan-2-yl)methanethiol；1,3-dioxolan-2-ylmethanethiol
• CAS: 5694-66-6
• 化学式: C₄H₈O₂S
• 分子量: 120.172
• InChiKey: GDBIKZDQPJKQBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  19.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-碘苯甲醚 、 [1,3]Dioxolan-2-yl-methanethiol 在 吡啶 、 2-丁烯酸乙酯 、 nickel dichloride 、 锌 作用下， 以 甲醇 为溶剂， 以74%的产率得到2-[(4-methoxyphenyl)thio]methyl-1,3-dioxolane
  参考文献：
  名称：

  Nickel-Mediated Inter- and Intramolecular C–S Coupling of Thiols and Thioacetates with Aryl Iodides at Room Temperature

  摘要：

  A Ni(0)-catalyzed intermolecular cross-coupling of various functionalized thiols and aryl Iodides has been developed and successfully extended to less explored intramolecular versions, where thioacetates could also be utilized as the strategic surrogate. Air-stable precatalysts, very mild conditions, and an easy protocol allow rapid access to medicinally useful aryl thioethers, as demonstrated in the facile synthesis of (+/-)-chuangxinmycin as a key step.

  DOI：

  10.1021/ol303366u
• 作为产物：
  描述：

  Thioacetic acid S-[1,3]dioxolan-2-ylmethyl ester 在 sodium hydroxide 作用下， 以 丙酮 为溶剂， 生成 [1,3]Dioxolan-2-yl-methanethiol
  参考文献：
  名称：

  A general and mild synthesis of thioesters and thiols from halides

  摘要：

  The conversion of a wide variety of halides to thioesters by reaction with potassium thiocetate under mild conditions is described, and the generality of the method is demonstrated. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02545-3

文献信息

• Nickel-Catalyzed C–S Reductive Cross-Coupling of Alkyl Halides with Arylthiosilanes toward Alkyl Aryl Thioethers
  作者：Yu-Zhong Yang、Yang Li、Gui-Fen Lv、De-Liang He、Jin-Heng Li

  DOI：10.1021/acs.orglett.2c01954

  日期：2022.7.22

  A nickel-catalyzed C–S reductive cross-coupling of alkyl halides with arylthiosilanes for producing alkyl aryl thioethers is developed. This reaction is initiated by umpolung transformations of arylthiosilanes followed by C–S reductive cross-coupling with alkyl halides to manage an electrophilic alkyl group onto the electrophilic sulfur atom and then construct a C(sp3)–S bond, and features exquisite

  开发了一种镍催化的烷基卤化物与芳基硫硅烷的 C-S 还原交叉偶联，用于生产烷基芳基硫醚。该反应由芳基硫硅烷的 umpolung 转变引发，然后与卤代烷发生 C-S 还原交叉偶联，将亲电烷基控制在亲电硫原子上，然后构建 C(sp 3 )-S 键，具有出色的化学选择性，对多种官能团具有优异的耐受性，并广泛应用于生物相关分子的后期修饰。
• DEINHAMMER, WOLFGANG
  作者：DEINHAMMER, WOLFGANG

  DOI：——

  日期：——