(S)-2-Hydroxy-1-((S)-2-methoxymethyl-pyrrolidin-1-yl)-2-phenyl-ethanone | 102061-03-0

• 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-Hydroxy-1-((S)-2-methoxymethyl-pyrrolidin-1-yl)-2-phenyl-ethanone
• 英文别名: (R)-2-Hydroxy-1-((S)-2-methoxymethyl-pyrrolidin-1-yl)-2-phenyl-ethanone；2-methoxymethylpyrrolidinyl mandelamide
• CAS: 102061-03-0；102061-05-2
• 化学式: C₁₄H₁₉NO₃
• 分子量: 249.31
• InChiKey: MSVWJWYSAJWWHF-UEWDXFNNSA-N

物化性质

• 沸点：
  419.0±35.0 °C(Predicted)
• 密度：
  1.165±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.36
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.77
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (S)-N-苯甲酰甲酰基-2-(甲氧基甲基)吡咯烷 在 samarium diiodide 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以92%的产率得到(S)-2-Hydroxy-1-((S)-2-methoxymethyl-pyrrolidin-1-yl)-2-phenyl-ethanone
  参考文献：
  名称：

  Diastereoselective reduction and carboncarbon bond formation of α-keto esters/amides with SmI2

  摘要：

  The stereoselective reduction of alpha -keto esters/alpha -keto amides, which have various chiral auxiliaries using SmI2, is examined. 2(S)-Methoxymethylpyrrolidine, 1,1,2(S)- and 1,1,2(R)-triphenylethanediol were found to be suitable chiral auxiliaries that produced the corresponding alpha -hydroxy ester and amide in good diastereoselectivity with satisfactory yields. Allylation, the Reformatsky-type reaction, and the ketyl-alkene coupling reaction with the 1,1,2(R)-triphenylethanediol and 2(S)-methoxymethylpyrrolidine, derivative of the alpha -keto ester/amide proceeded smoothly with high diastereoselectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00676-1

文献信息

• Asymmetric synthesis of α-hydroxy carboxylic acids: direct oxidation of chiral amide enolates using 2-sulfonyloxaziridines
  作者：Franklin A. Davis、Lal C. Vishwakarma

  DOI：10.1016/s0040-4039(00)89185-6

  日期：1985.1

  The direct oxidation of chiral amide enolates to optically active mandelic acid using 2-sulfonyloxaziridine is described. The diastereoselectivity is counterion dependent.

  描述了使用2-磺酰基氧杂氮丙啶将手性酰胺烯酸酯直接氧化成旋光扁桃酸。非对映选择性取决于抗衡离子。