S-benzyl quinoline-2-carbothioate | 1215309-99-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: S-benzyl quinoline-2-carbothioate
• CAS: 1215309-99-1
• 化学式: C₁₇H₁₃NOS
• 分子量: 279.362
• InChiKey: CYCCCJKZGUNXHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  55.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  在 三乙烯二胺 、 水 作用下， 生成 S-benzyl quinoline-2-carbothioate
  参考文献：
  名称：

  Solvent-Free Conversion of Thioamides to Thioesters

  摘要：

  [image omitted] Diverse thioesters were efficiently prepared via the solvent-free reaction of thioamide derivatives with alkyl halides in the presence of catalytic amounts of 1,4-diazabicyclo[2.2.2]octane (DABCO) in small quantities of water and in good to excellent yields.

  DOI：

  10.1080/00397911.2010.503001

文献信息

• Ynamide-Mediated Thioester Synthesis
  作者：Xuewei Wang、Yongli Zhao、Jinhua Yang、Yanxi Li、Ying Luo、Mengyao Xu、Junfeng Zhao

  DOI：10.1021/acs.joc.1c01949

  日期：2021.12.17

  A novel ynamide-mediated thioester synthesis strategy was developed. Importantly, no detectable racemization was observed for the thioesterifications of carboxylic acids containing an α-chiral center, enabling it to be useful for the synthesis of peptide thioester, which is the key component of native chemical ligation. It is worth mentioning that amino acid side chain functional groups such as -OH

  开发了一种新的 ynamide 介导的硫酯合成策略。重要的是，对于含有 α-手性中心的羧酸的硫酯化，没有观察到可检测到的外消旋化，这使其可用于合成肽硫酯，这是天然化学连接的关键成分。值得一提的是，-OH和吲哚-NH等氨基酸侧链官能团与反应条件相容，无需对其进行保护。此外，这种方法也适用于硒代酯。
• Highly efficient synthesis of thioesters in water
  作者：Hassan Zali Boeini、Maryam Eshghi Kashan

  DOI：10.1039/b916852d

  日期：——

  Thioesters were efficiently prepared via the direct reaction of tertiary thioamides and alkyl halides in water, and in the presence of catalytic amounts of NaI, hexadecyltrimethylammonium bromide (HTAB), and 1,4-diazabicyclo[2.2.2]octane (DABCO). Hence, thioamides smoothly undergo an S-alkylation with alkyl halides in aqueous media following by hydrolysis to afford the corresponding thioesters in very good to excellent yields.

  在 NaI、十六烷基三甲基溴化铵（HTAB）和 1,4-二氮杂双环[2.2.2]辛烷（DABCO）的催化下，通过叔硫酰胺和烷基卤化物在水中的直接反应，可以高效地制备硫代酯。因此，硫代酰胺在水介质中可以顺利地与烷基卤化物发生 S-烷基化反应，然后通过水解得到相应的硫代酯，收率非常好甚至非常高。