(2R,3S,4S)-2-fluoro-3-tosylmethyl-2-trifluoromethyl-4-pentanolide | 183903-78-8

• 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: (2R,3S,4S)-2-fluoro-3-tosylmethyl-2-trifluoromethyl-4-pentanolide
• 英文别名: (3R,4S,5S)-3-fluoro-5-methyl-4-[(4-methylphenyl)sulfonylmethyl]-3-(trifluoromethyl)oxolan-2-one
• CAS: 183903-78-8
• 化学式: C₁₄H₁₄F₄O₄S
• 分子量: 354.322
• InChiKey: YSICUQJGYZMSFI-XHVZSJERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S)-2-fluoro-3-tosylmethyl-2-trifluoromethyl-4-pentanolide 在 2-羟基吡啶 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 23.0h， 生成 (+/-)-(2S,3R,4S)-2-benzylamino-2-trifluoromethyl-3-tosylmethyl-4-pentanolide
  参考文献：
  名称：

  Novel Synthesis of α-Trifluoromethylated α-Amino Acid Derivatives from γ-Hydroxy-α-fluoro-α-trifluoromethyl Carboxamides

  摘要：

  On treatment with an organoaluminum reagent such as trimethylaluminum or DIBAL-H, gamma-hydroxy-alpha-fluoro-alpha-trifluoromethyl carboxamides (1) give a single diastereomer of alpha-amino-alpha-trifluoromethyl-gamma-lactones (2), which are a ring-closed form of gamma-hydroxy-alpha-trifluoromethyl-alpha-amino acids. This intriguing reaction results from intramolecular replacement of the fluorine atom on the alpha-carbon atom with the nitrogen atom of the amide group, which occurs in an S(N)2 manner.

  DOI：

  10.1021/ol047683y
• 作为产物：
  描述：

  rac-(E)-3-hydroxy-1-tosyl-1-butene 在 乙酸乙烯酯 、 Lipase PS 作用下， 以 氯仿 、 苯 为溶剂， 反应 7.0h， 生成 (2R,3S,4S)-2-fluoro-3-tosylmethyl-2-trifluoromethyl-4-pentanolide
  参考文献：
  名称：

  Novel Synthesis of α-Trifluoromethylated α-Amino Acid Derivatives from γ-Hydroxy-α-fluoro-α-trifluoromethyl Carboxamides

  摘要：

  On treatment with an organoaluminum reagent such as trimethylaluminum or DIBAL-H, gamma-hydroxy-alpha-fluoro-alpha-trifluoromethyl carboxamides (1) give a single diastereomer of alpha-amino-alpha-trifluoromethyl-gamma-lactones (2), which are a ring-closed form of gamma-hydroxy-alpha-trifluoromethyl-alpha-amino acids. This intriguing reaction results from intramolecular replacement of the fluorine atom on the alpha-carbon atom with the nitrogen atom of the amide group, which occurs in an S(N)2 manner.

  DOI：

  10.1021/ol047683y

文献信息

• Stereoselective formation of α-fluoro-α-trifluoromethyl-γ-lactones starting from γ-hydroxy-α,β-unsaturated sulfones and a hexafluoropropene-diethylamine adduct (PPDA)
  作者：Katsuyuki Ogura、Ken-ichi Ogu、Takashi Ayabe、Jun-ichi Sonehara、Motohiro Akazome

  DOI：10.1016/s0040-4039(97)01120-9

  日期：1997.7

  (E)-3-Hydroxy-1-alkenyl p-tolyl sulfones (1) reacted with a hexafluoropropen-diethylamine adduct (PPDA) to afford alpha-fluoro-alpha-(trifluoromethyl)-beta-[(p-tolylsulfonyl)methyl]-gamma-lactones (2). This reaction is so stereoselective that only one diastereomer of 2 is detected in the reaction mixture. A plausible mechanism for this intriguing reaction is discussed. (C) 1997 Elsevier Science Ltd.

  (E)-3-羟基-1-烯丙基二甲苯 sulfonyl 化物 (1) 与六氟丙二胺加成物 (PPDA) 反应，生成 alpha-氟基-α-( trifluoromethyl ) -beta-[(p-甲基苯 sulfonyl )甲基]-gamma-环状物 (2)。本反应如此立体选择性，反应体系中只能检测到产物 2 的一种对映异构。对于这一引人注目的反应，提出了一个合理的机制。 (C) 1997 Elsevier Science Ltd.
• Novel Synthesis of α-Trifluoromethylated α-Amino Acid Derivatives from γ-Hydroxy-α-fluoro-α-trifluoromethyl Carboxamides
  作者：Kenichi Ogu、Shoji Matsumoto、Motohiro Akazome、Katsuyuki Ogura

  DOI：10.1021/ol047683y

  日期：2005.2.1

  On treatment with an organoaluminum reagent such as trimethylaluminum or DIBAL-H, gamma-hydroxy-alpha-fluoro-alpha-trifluoromethyl carboxamides (1) give a single diastereomer of alpha-amino-alpha-trifluoromethyl-gamma-lactones (2), which are a ring-closed form of gamma-hydroxy-alpha-trifluoromethyl-alpha-amino acids. This intriguing reaction results from intramolecular replacement of the fluorine atom on the alpha-carbon atom with the nitrogen atom of the amide group, which occurs in an S(N)2 manner.