(S)-4-{[(1-propyl-1H-imidazol-5-yl)methyl]sulfinyl}phenylammonium (2S,3S)-2,3-bis-[(4-methylbenzoyl)oxy]-butenoate

• 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-{[(1-propyl-1H-imidazol-5-yl)methyl]sulfinyl}phenylammonium (2S,3S)-2,3-bis-[(4-methylbenzoyl)oxy]-butenoate
• 英文别名: (S)-4-(((1-propyl-1H-imidazol-5-yl)methyl)sulfinyl)aniline di-p-toluoyl-D-tartrate；(2S,3S)-2,3-bis[(4-methylbenzoyl)oxy]butanedioic acid;4-[(S)-(3-propylimidazol-4-yl)methylsulfinyl]aniline
• 化学式: C₁₃H₁₇N₃OS*C₂₀H₁₈O₈
• 分子量: 649.722
• InChiKey: ANZGIZFSZLWEIR-JWCUXBRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.41
• 重原子数：
  46
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  207
• 氢给体数：
  3
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (S)-4-{[(1-propyl-1H-imidazol-5-yl)methyl]sulfinyl}phenylammonium (2S,3S)-2,3-bis-[(4-methylbenzoyl)oxy]-butenoate 在 盐酸 、 potassium carbonate 作用下， 以 水 、 乙酸乙酯 为溶剂， 生成 4-[(S)-(1-丙基-1H-咪唑-5-基)甲亚磺酰基]苯胺
  参考文献：
  名称：

  EP1593680

  摘要：

  公开号：
• 作为产物：
  描述：

  4-氨基苯硫酚 在 双氧水 、 三乙胺 作用下， 以 水 、 异丙醇 、 甲苯 为溶剂， 反应 504001.0h， 生成 (S)-4-{[(1-propyl-1H-imidazol-5-yl)methyl]sulfinyl}phenylammonium (2S,3S)-2,3-bis-[(4-methylbenzoyl)oxy]-butenoate
  参考文献：
  名称：

  Unusual asymmetric oxidation of sulfide; the diastereoselective oxidation of prochiral sulfide-chiral acid salt with hydrogen peroxide without metal

  摘要：

  The sulfide 4 was treated with chiral acid in a mixture of toluene and methyl iso-butylketone to precipitate the salt, which reacted with 30% H2O2 for 3 weeks at rt. The resulting crystals were collected followed by recrystallization to give the salt of enantiometrically pure sulfoxide and chiral acid 7 in 72% yield and 98.1% de, which was led to chiral sulfoxide S-3 after neutralization. Sulfoxide S-3 was led to S-1a as the candidate for an orally active HIV-1 therapeutic agent. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.03.036

文献信息

• EP1593681
  申请人：——

  公开号：——

  公开（公告）日：——
• EP1593680
  申请人：——

  公开号：——

  公开（公告）日：——
• Unusual asymmetric oxidation of sulfide; the diastereoselective oxidation of prochiral sulfide-chiral acid salt with hydrogen peroxide without metal
  作者：Tomomi Ikemoto、Atsuko Nishiguchi、Tatsuya Ito、Hiroyuki Tawada

  DOI：10.1016/j.tet.2005.03.036

  日期：2005.5

  The sulfide 4 was treated with chiral acid in a mixture of toluene and methyl iso-butylketone to precipitate the salt, which reacted with 30% H2O2 for 3 weeks at rt. The resulting crystals were collected followed by recrystallization to give the salt of enantiometrically pure sulfoxide and chiral acid 7 in 72% yield and 98.1% de, which was led to chiral sulfoxide S-3 after neutralization. Sulfoxide S-3 was led to S-1a as the candidate for an orally active HIV-1 therapeutic agent. (c) 2005 Elsevier Ltd. All rights reserved.