(S)-2-(4-phenoxyphenylsulfonylmethyl)oxirane | 868389-09-7

• 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)-2-(4-phenoxyphenylsulfonylmethyl)oxirane
• 英文别名: (2S)-2-[(4-phenoxyphenyl)sulfonylmethyl]oxirane
• CAS: 868389-09-7
• 化学式: C₁₅H₁₄O₄S
• 分子量: 290.34
• InChiKey: VOOWDBLHARNLGM-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  64.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-(4-phenoxyphenylsulfonylmethyl)oxirane 在 硫脲 作用下， 以 甲醇 为溶剂， 以84%的产率得到(R)-2-(4-phenoxyphenylsulfonylmethyl)thiirane
  参考文献：
  名称：

  Synthesis of Chiral 2-(4-Phenoxyphenylsulfonylmethyl)thiiranes as Selective Gelatinase Inhibitors

  摘要：

  Compound 1, 2-(4-phenoxyphenyisulfonylmethyl)thiirane, is a selective inhibitor of gelatinases, which is showing high promise in studies of animal models for cancer metastasis and stroke. The (R)-1 and (S)-1 enantiomers; of compound 1 were each synthesized in this study and were shown to be equally active in inhibition of gelatinases.

  DOI：

  10.1021/ol0517269
• 作为产物：
  描述：

  (R)-1-chloro-3-(4-phenoxyphenylsulfanyl)propan-2-ol 在 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 1.17h， 生成 (S)-2-(4-phenoxyphenylsulfonylmethyl)oxirane
  参考文献：
  名称：

  Synthesis of Chiral 2-(4-Phenoxyphenylsulfonylmethyl)thiiranes as Selective Gelatinase Inhibitors

  摘要：

  Compound 1, 2-(4-phenoxyphenyisulfonylmethyl)thiirane, is a selective inhibitor of gelatinases, which is showing high promise in studies of animal models for cancer metastasis and stroke. The (R)-1 and (S)-1 enantiomers; of compound 1 were each synthesized in this study and were shown to be equally active in inhibition of gelatinases.

  DOI：

  10.1021/ol0517269

文献信息

• Synthesis of Chiral 2-(4-Phenoxyphenylsulfonylmethyl)thiiranes as Selective Gelatinase Inhibitors
  作者：Mijoon Lee、M. Margarida Bernardo、Samy O. Meroueh、Stephen Brown、Rafael Fridman、Shahriar Mobashery

  DOI：10.1021/ol0517269

  日期：2005.9.1

  Compound 1, 2-(4-phenoxyphenyisulfonylmethyl)thiirane, is a selective inhibitor of gelatinases, which is showing high promise in studies of animal models for cancer metastasis and stroke. The (R)-1 and (S)-1 enantiomers; of compound 1 were each synthesized in this study and were shown to be equally active in inhibition of gelatinases.