S-[(Z)-1-phenylprop-1-enyl] N-methyl-N-phenylcarbamothioate | 1430333-12-2

• 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: S-[(Z)-1-phenylprop-1-enyl] N-methyl-N-phenylcarbamothioate
• CAS: 1430333-12-2
• 化学式: C₁₇H₁₇NOS
• 分子量: 283.394
• InChiKey: FTAFKIWOJJNWRN-XFQLMFQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  S-(1-phenylallyl)-1H-imidazole-1-carbothioate 在 sodium hydride 、 三氟甲烷磺酸甲酯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.5h， 生成 S-[(Z)-1-phenylprop-1-enyl] N-methyl-N-phenylcarbamothioate 、
  参考文献：
  名称：

  Carbolithiation of S-Alkenyl-N-aryl Thiocarbamates: Carbanion Arylation in a Connective Route to Tertiary Thiols

  摘要：

  S-Alkenyl-N-arylthiocarbamates are formed from allylic alcohols by sigmatropic rearrangement and isomerization or C=C bond cleavage. They undergo carbolithiation with a range of organolithium reagents, generating benzyllithium intermediates in a stereospecific manner which may undergo N to C aryl migration to yield thiocarbamates with tertiary substituents. A simple base-promoted alcoholysis reveals a series of hindered tertiary thiols with branched carbon skeletons.

  DOI：

  10.1021/ol400570r

文献信息

• Carbolithiation of <i>S</i>-Alkenyl-<i>N</i>-aryl Thiocarbamates: Carbanion Arylation in a Connective Route to Tertiary Thiols
  作者：Daniele Castagnolo、Daniel J. Foley、Hatice Berber、Renzo Luisi、Jonathan Clayden

  DOI：10.1021/ol400570r

  日期：2013.5.3

  S-Alkenyl-N-arylthiocarbamates are formed from allylic alcohols by sigmatropic rearrangement and isomerization or C=C bond cleavage. They undergo carbolithiation with a range of organolithium reagents, generating benzyllithium intermediates in a stereospecific manner which may undergo N to C aryl migration to yield thiocarbamates with tertiary substituents. A simple base-promoted alcoholysis reveals a series of hindered tertiary thiols with branched carbon skeletons.