S-methyl azepane-1-carbothioate | 3134-64-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环庚烷
• 英文名称: S-methyl azepane-1-carbothioate
• 英文别名: azepane-1-carbothioic acid S-methyl ester；(Azepana1ayl)(methylsulfanyl)methanone
• CAS: 3134-64-3
• 化学式: C₈H₁₅NOS
• 分子量: 173.279
• InChiKey: OGCIYYDDRZYHNF-UHFFFAOYSA-N

物化性质

• 沸点：
  129.5-130.5 °C(Press: 10 Torr)
• 密度：
  1.079±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  45.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  环己亚胺 、 一氧化碳 、 碘甲烷 在 sulfur 作用下， 以 二甲基亚砜 为溶剂， 20.0 ℃ 、101.32 kPa 条件下， 反应 6.0h， 以88%的产率得到S-methyl azepane-1-carbothioate
  参考文献：
  名称：

  Solvent-assisted thiocarboxylation of amines and alcohols with carbon monoxide and sulfur under mild conditions

  摘要：

  DMSO or DMF as a solvent strongly accelerated the thiocarboxylation of amines and alcohols with carbon monoxide and sulfur. Under mild conditions (1 atm, 20 degrees C), this thiocarboxylation of amines assisted by DMSO with carbon monoxide and sulfur has been developed into a practical and convenient synthetic method for S-alkyl thiocarbamates in good to excellent yields, including EPTC, thiobencarb, orbercarb, and molinate (herbicides). DMF also showed the similar solvent effect. NMP slightly decreased the effect for the thiocarboxylation of amines, and the yield of S-alkyl thiocarbamate was lowered in DMAc. Surprisingly, no formation of S-alkyl thiocarbamate was observed at the use of the other solvents, such as THF, hexane, toluene, AcOEt, MeCN, MeOH, and H2O. The present solvent-assisted thiocarboxylation with carbon monoxide and sulfur could be also applied to a new synthesis of S-alkyl O-alkyl carbonothioates from alcohols under mild conditions (1 atm, 20 degrees C) in DMF using DBU (1,8-diazabicyclo[5.4.0]undec-7-ene). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.06.114

文献信息

• Solvent-assisted thiocarboxylation of amines and alcohols with carbon monoxide and sulfur under mild conditions
  作者：Takumi Mizuno、Toshiyuki Iwai、Yoshio Ishino

  DOI：10.1016/j.tet.2005.06.114

  日期：2005.9

  DMSO or DMF as a solvent strongly accelerated the thiocarboxylation of amines and alcohols with carbon monoxide and sulfur. Under mild conditions (1 atm, 20 degrees C), this thiocarboxylation of amines assisted by DMSO with carbon monoxide and sulfur has been developed into a practical and convenient synthetic method for S-alkyl thiocarbamates in good to excellent yields, including EPTC, thiobencarb, orbercarb, and molinate (herbicides). DMF also showed the similar solvent effect. NMP slightly decreased the effect for the thiocarboxylation of amines, and the yield of S-alkyl thiocarbamate was lowered in DMAc. Surprisingly, no formation of S-alkyl thiocarbamate was observed at the use of the other solvents, such as THF, hexane, toluene, AcOEt, MeCN, MeOH, and H2O. The present solvent-assisted thiocarboxylation with carbon monoxide and sulfur could be also applied to a new synthesis of S-alkyl O-alkyl carbonothioates from alcohols under mild conditions (1 atm, 20 degrees C) in DMF using DBU (1,8-diazabicyclo[5.4.0]undec-7-ene). (c) 2005 Elsevier Ltd. All rights reserved.