α-(trimethylsilyl)benzylthiol | 38225-20-6

• 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: α-(trimethylsilyl)benzylthiol
• 英文别名: α-trimethylsilylbenzylthiol；α-Mercapto-α-trimethylsilyltoluol；Trimethylsilylbenzylmercaptan；Phenyl(trimethylsilyl)methanethiol
• CAS: 38225-20-6
• 化学式: C₁₀H₁₆SSi
• 分子量: 196.389
• InChiKey: JYHLOQOGMLYWOI-UHFFFAOYSA-N

物化性质

• 沸点：
  232.5±28.0 °C(Predicted)
• 密度：
  0.954±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.53
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  α-(trimethylsilyl)benzylthiol 在 N-溴代丁二酰亚胺(NBS) 、 sodium hydride 作用下， 以 四氢呋喃 、 四氯化碳 为溶剂， 生成 [Bromo(phenyl){[(trimethylsilyl)methyl]sulfanyl}methyl](trimethyl)silane
  参考文献：
  名称：

  Terao, Yoshiyasu; Aono, Masahiro; Imai, Nobuyuki, Chemical and pharmaceutical bulletin, 1987, vol. 35, # 5, p. 1734 - 1740

  摘要：

  DOI：
• 作为产物：
  描述：

  三甲基氯硅烷 、 lithium phenylmethanethiolate 生成 α-(trimethylsilyl)benzylthiol
  参考文献：
  名称：

  Seebach,D.; Geiss,K.-H., Angewandte Chemie, 1974, vol. 86, p. 202 - 203

  摘要：

  DOI：

文献信息

• A novel synthesis of silyl enol ethers from α-silylbenzylthiols and carboxylic acid derivatives via CC bond formation; thermal rearrangement of S-α-silylbenzyl thioesters
  作者：Mitsuo Komatsu、Choi Jinil、Eiichiro Imai、Yoji Oderaotoshi、Satoshi Minakata

  DOI：10.1016/s0040-4039(01)02029-9

  日期：2001.12

  A new procedure for the synthesis of silyl enol ethers from S-α-silylbenzyl thioesters without need for either bases or catalysts via CC bond formation is described. Solutions of S-α-silylbenzyl thioesters were simply heated at 180°C for 24 h in a sealed tube to give silyl enol ethers in good yields with high stereoselectivity. Cyclization of the dipoles generated by thermal rearrangement of the silyl

  描述了由S -α-甲硅烷基苄基硫代酯合成甲硅烷基烯醇醚的新方法，该过程不需要通过C viaC键形成的碱或催化剂。解小号-α-silylbenzyl硫酯是在一个密封管中在180℃下简单地加热24小时，得到甲硅烷基烯醇醚以良好的收率高立体选择性。通过甲硅烷基基团的热重排和消除硫产生的偶极的环化提供了甲硅烷基烯醇醚。
• Geiss,K.-H. et al., Chemische Berichte, 1977, vol. 110, p. 1833 - 1851
  作者：Geiss,K.-H. et al.

  DOI：——

  日期：——
• Generation of thioaldehydes via fluoride induced elimination of α-silyldisulfides
  作者：Grant A. Krafft、Peter T. Meinke

  DOI：10.1016/s0040-4039(00)98348-5

  日期：1985.1
• 1,4-Silatropy of <i>S</i>-α-Silylbenzyl Thioesters:  A Convenient Route to Silyl Enol and Dienol Ethers Accompanied by C−C Bond Formation via Thiocarbonyl Ylides
  作者：Jinil Choi、Eiichiro Imai、Masatoshi Mihara、Yoji Oderaotoshi、Satoshi Minakata、Mitsuo Komatsu

  DOI：10.1021/jo026211z

  日期：2003.8.1

  A novel convenient method for the generation of thiocarbonyl ylides from readily accessible starting materials and the first synthetic application of in situ generated ylides in the synthesis of silyl enol and dienol ethers, accompanied by C-C bond formation, is described. Under completely neutral conditions without any catalyst or additive, thermal reactions of S-alpha-silylbenzyl thioesters in sealed tubes at 180 degreesC provided silyl enol and dienol ethers in good to excellent yields with high stereoselectivities. This procedure consists of a multistep reaction in a one-pot process, i.e., 1,4-silatropy of S-alpha-silylbenzyl thioesters to give thiocarbonyl ylides, 1,3-electrocyclization of the ylides to give thiiranes, and the extrusion of sulfur from thiiranes to give silyl enol and dienol ethers.
• TERAO, YOSHIYASU;AONO, MASAHIRO;IMAI, NOBUYUKI;ACHIWA, KAZUO, CHEM. AND PHARM. BULL., 35,(1987) N 5, 1734-1740
  作者：TERAO, YOSHIYASU、AONO, MASAHIRO、IMAI, NOBUYUKI、ACHIWA, KAZUO

  DOI：——

  日期：——