(R)-methyl 3-(phenylthio)butanoate | 119873-30-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (R)-methyl 3-(phenylthio)butanoate
• 英文别名: (R)-methyl 3-phenylthiobutanoate；methyl (3R)-3-phenylsulfanylbutanoate
• CAS: 119873-30-2
• 化学式: C₁₁H₁₄O₂S
• 分子量: 210.297
• InChiKey: HGIOPWJVKFOFPO-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  methyl (3R)-3-(2-aminophenyl)sulfanylbutanoate 在 硫酸 、 次磷酸 、 sodium nitrite 作用下， 以 水 为溶剂， 以35%的产率得到(R)-methyl 3-(phenylthio)butanoate
  参考文献：
  名称：

  Oxazepines and thiazepines. XIX Synthesis of optically active 2,3-dihydro-1,5-benzothiazepin-4(5H)-ones

  摘要：

  DOI：

  10.1007/bf00810103

文献信息

• Organocatalytic Asymmetric Sulfa-Michael Addition of Thiols to α,β-Unsaturated Hexafluoroisopropyl Esters: Expeditious Access to (<i>R</i>)-Thiazesim
  作者：Xin Fang、Jun Li、Chun-Jiang Wang

  DOI：10.1021/ol4015305

  日期：2013.7.5

  A highly efficient organocatalytic asymmetric SMA reaction of hexafluoroisopropyl alpha,beta-unsaturated esters has been developed. Introducing electron-withdrawing hexafluoroisopropyl ester is crucial to enhancing the electrophilicity of unsaturated esters as SMA acceptors. The catalytic system performs well over a broad scope of alpha,beta-unsaturated esters and diversified thiols and provides facile access to (R)-thiazesim in a one-pot protocol.
• Steric Tuning of Reactivity and Enantioselectivity in Addition of Thiophenol to Enoates Catalyzed by an External Chiral Ligand
  作者：Katsumi Nishimura、Masashi Ono、Yasuo Nagaoka、Kiyoshi Tomioka

  DOI：10.1021/ja9729950

  日期：1997.12.1
• Structural requirements of a chiral ligand for the catalytic asymmetric addition of thiophenol to α,β-unsaturated esters
  作者：Kiyoshi Tomioka、Manabu Okuda、Katsumi Nishimura、Shino Manabe、Motomu Kanai、Yasuo Nagaoka、Kenji Koga

  DOI：10.1016/s0040-4039(98)00080-x

  日期：1998.4

  The tridentate amino ether ligands 1 and 14 were developed through systematic structural modification of the bidentate diether ligand 2. The reaction of thiophenol with methyl crotonate was catalyzed by 14 and lithium thiophenolate to afford (S)-methyl 3-phenylthiobutanoate in 75% ee and 95% yield. (C) 1998 Elsevier Science Ltd. All rights reserved.
• PUZICHA, GISBERT;LEVAI, ALBERT;SZILAGYI, LASZLO, MONATSH. CHEM., 119,(1988) N-9, C. 933-944
  作者：PUZICHA, GISBERT、LEVAI, ALBERT、SZILAGYI, LASZLO

  DOI：——

  日期：——