(S)-4-aminobenzyl methyl sulfoxide | 168028-58-8

• 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)-4-aminobenzyl methyl sulfoxide
• 英文别名: 4-[[(S)-methylsulfinyl]methyl]aniline
• CAS: 168028-58-8
• 化学式: C₈H₁₁NOS
• 分子量: 169.247
• InChiKey: ZHPRIDXERKSLCY-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.15
• 重原子数：
  11.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  43.09
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (S)-4-aminobenzyl methyl sulfoxide 在 吡啶 作用下， 生成 (S)-4-acetamidobenzyl methyl sulfoxide
  参考文献：
  名称：

  Biotransformation of organic sulfides. Part 6. Formation of chiral para-substituted benzyl methyl sulfoxides by Helminthosporium species NRRL 4671

  摘要：

  The fungus Helminthosporium species NRRL 4671 has been used for the biotransformation of a series of para-substituted benzyl sulfides with substituent groups consisting of trifluoromethyl, halo, hydroxy, methoxy, acetoxy, nitro, cyano, amino, acetamido, acyl and carboxylic acid units. In all cases, sulfoxide formation occurred in good yield and with predominant (S) chirality at the sulfur position. A minor amount of sulfone product was also obtained from the halo- and methoxy-substituted substrates.

  DOI：

  10.1016/0957-4166(95)00199-y
• 作为产物：
  描述：

  -methyl-sulfid 在 盐酸 、 tin 作用下， 以 乙醇 为溶剂， 反应 48.5h， 生成 (S)-4-aminobenzyl methyl sulfoxide
  参考文献：
  名称：

  Biotransformation of organic sulfides. Part 6. Formation of chiral para-substituted benzyl methyl sulfoxides by Helminthosporium species NRRL 4671

  摘要：

  The fungus Helminthosporium species NRRL 4671 has been used for the biotransformation of a series of para-substituted benzyl sulfides with substituent groups consisting of trifluoromethyl, halo, hydroxy, methoxy, acetoxy, nitro, cyano, amino, acetamido, acyl and carboxylic acid units. In all cases, sulfoxide formation occurred in good yield and with predominant (S) chirality at the sulfur position. A minor amount of sulfone product was also obtained from the halo- and methoxy-substituted substrates.

  DOI：

  10.1016/0957-4166(95)00199-y

文献信息

• Active site model of cyclohexanone monooxygenase. 3. The case of benzyl sulfides bearing polar groups
  作者：Gianluca Ottolina、Piero Pasta、David Varley、Herbert L. Holland

  DOI：10.1016/s0957-4166(96)00450-8

  日期：1996.12

  The stereopreference of cyclohexanone monooxygenase for a series of benzyl methyl sulfides bearing in the p-position groups with different σp values has been rationalized by locating inside the enzyme active site model electron-rich and electron-poor regions.

  环己酮单加氧酶的一系列苄基甲基硫化物在轴承的stereopreference p位上基团与不同的σ p值已经由酶活性位点模型富电子和缺电子的区域内定位合理化。