S-Naphthalen-2-yl cyclohexanecarbothioate | 155784-66-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: S-Naphthalen-2-yl cyclohexanecarbothioate
• CAS: 155784-66-0
• 化学式: C₁₇H₁₈OS
• 分子量: 270.395
• InChiKey: WKWVDMDJGGYSAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  S-Naphthalen-2-yl cyclohexanecarbothioate 在 1,4-环己二烯 作用下， 以 苯 为溶剂， 反应 116.0h， 生成 环己烷基甲醛
  参考文献：
  名称：

  Generation of Acyl Radicals From 2-Naphthyl Thioesters

  摘要：

  A series of S-2-naphthyl thioesters were synthesized from the corresponding carboxylic acids or acid chlorides. Irradiation of these thioesters in the presence of a hydrogen source (i.e., 1,4-cyclohexadiene) generated the corresponding aldehydes. In this fashion, primary, secondary, tertiary, and aryl carboxylic acids were converted to the aldehydes in high yields. Intramolecular radical cyclization reactions support the hypothesis that the reaction proceeds via the formation of acyl radicals. The formation of aldehydes was not perturbed by possible Norrish Type II reactions.

  DOI：

  10.1021/jo00088a053
• 作为产物：
  描述：

  环己甲酸 在 吡啶 、 氯化亚砜 作用下， 以 苯 为溶剂， 反应 4.5h， 生成 S-Naphthalen-2-yl cyclohexanecarbothioate
  参考文献：
  名称：

  Generation of Acyl Radicals From 2-Naphthyl Thioesters

  摘要：

  A series of S-2-naphthyl thioesters were synthesized from the corresponding carboxylic acids or acid chlorides. Irradiation of these thioesters in the presence of a hydrogen source (i.e., 1,4-cyclohexadiene) generated the corresponding aldehydes. In this fashion, primary, secondary, tertiary, and aryl carboxylic acids were converted to the aldehydes in high yields. Intramolecular radical cyclization reactions support the hypothesis that the reaction proceeds via the formation of acyl radicals. The formation of aldehydes was not perturbed by possible Norrish Type II reactions.

  DOI：

  10.1021/jo00088a053

文献信息

• Beyond Amide Bond Formation: TCFH as a Reagent for Esterification
  作者：Nathaniel R. Luis、Kasey K. Chung、Matthew R. Hickey、Ziqing Lin、Gregory L. Beutner、David A. Vosburg

  DOI：10.1021/acs.orglett.3c01611

  日期：2024.4.12

  In this Communication, an investigation of the combination of N,N,N′,N′-tetramethylchloroformamidinium hexafluorophosphate (TCFH) and N-methylimidazole (NMI) for the synthesis of esters and thioesters is described. This work revealed the unique challenges of the reactions of less nucleophilic alcohols and more reactive thiols with the N-acyl imidazolium intermediate and led to the identification of

  在本通讯中，描述了N , N , N ', N '-四甲基氯甲脒六氟磷酸盐 (TCFH) 和N-甲基咪唑 (NMI) 组合用于合成酯和硫酯的研究。这项工作揭示了亲核性较低的醇和反应性较高的硫醇与N-酰基咪唑鎓中间体反应的独特挑战，并确定了为一系列醇和硫醇提供高产率和选择性的一般有利条件。
• Penn John H., Liu Fang, J. Org. Chem, 59 (1994) N 9, S 2608-2612
  作者：Penn John H., Liu Fang

  DOI：——

  日期：——
• Generation of Acyl Radicals From 2-Naphthyl Thioesters
  作者：John H. Penn、Fang Liu

  DOI：10.1021/jo00088a053

  日期：1994.5

  A series of S-2-naphthyl thioesters were synthesized from the corresponding carboxylic acids or acid chlorides. Irradiation of these thioesters in the presence of a hydrogen source (i.e., 1,4-cyclohexadiene) generated the corresponding aldehydes. In this fashion, primary, secondary, tertiary, and aryl carboxylic acids were converted to the aldehydes in high yields. Intramolecular radical cyclization reactions support the hypothesis that the reaction proceeds via the formation of acyl radicals. The formation of aldehydes was not perturbed by possible Norrish Type II reactions.