(S)-4-chlorobenzyl methyl sulfoxide | 168028-53-3

• 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-chlorobenzyl methyl sulfoxide
• 英文别名: p-chlorobenzyl methyl sulfoxide；1-Chloro-4-{[(S)-methanesulfinyl]methyl}benzene；1-chloro-4-[[(S)-methylsulfinyl]methyl]benzene
• CAS: 168028-53-3
• 化学式: C₈H₉ClOS
• 分子量: 188.678
• InChiKey: OYNKDWZZTONUIY-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-氯苄基甲基硫醚 以 乙醇 为溶剂， 反应 48.0h， 以12%的产率得到4-chlorobenzyl methyl sulfone
  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

• Enantioselective inclusion of (R)-phenylglycyl-(R)-phenylglycine with benzyl methyl sulfoxides
  作者：Motohiro Akazome、Atsushi Hirabayashi、Katsuyuki Ogura

  DOI：10.1016/j.tet.2004.10.032

  日期：2004.12

  (RR-1), recognized p-halobenzyl methyl sulfoxides with high R-enantioselectivity (86–99% ee) to form inclusion compounds. The single-crystal X-ray analyses showed that RR-1 molecules are arranged in parallel and zigzags via hydrogen bonding to construct a pleated sheet. The guest molecules that form hydrogen bond with +NH3 of RR-1 are accommodated in the channel cavity between the layers. In contrast to

  结晶的二肽（R）-苯基甘氨酰-（R）-苯基甘氨酸（RR - 1）识别具有高R-对映选择性（86-99％ee）的对卤代苄基甲基亚砜，形成包合物。X射线单晶分析表明，RR - 1分子平行排列，并通过氢键呈锯齿形，构成褶皱片。客体分子形式氢键+ NH 3的RR - 1被容纳在各层之间的通道腔中。与其中形成矩形空腔的母体苄基甲基亚砜的包合物晶体相反，包括对-卤代苄基甲基亚砜的空腔变成菱形。我们还检查了这些包合物中的客体交换，发现当主体结构发生变化时便发生客体交换。
• Biotransformation of organic sulfides. Part 6. Formation of chiral para-substituted benzyl methyl sulfoxides by Helminthosporium species NRRL 4671
  作者：Herbert L. Holland、Frances M. Brown、Brett G. Larsen

  DOI：10.1016/0957-4166(95)00199-y

  日期：1995.7

  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.