(3S,4R,1'S)-4-benzoyloxymethyl-3-hydroxy-1-(1'-phenylethyl)pyrrolidin-2-one | 859214-18-9

• 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: (3S,4R,1'S)-4-benzoyloxymethyl-3-hydroxy-1-(1'-phenylethyl)pyrrolidin-2-one
• CAS: 859214-18-9
• 化学式: C₂₀H₂₁NO₄
• 分子量: 339.391
• InChiKey: CXCKFKQHFXXYAM-QGTPRVQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.42
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  66.84
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (3S,4R,1'S)-4-benzoyloxymethyl-3-hydroxy-1-(1'-phenylethyl)pyrrolidin-2-one 在 sodium azide 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 6.0h， 生成 (3R,4S,1'S)-3-azido-4-benzoyloxymethyl-1-(1'-phenylethyl)pyrrolidin-2-one
  参考文献：
  名称：

  Chiral 3-hydroxypyrrolidin-2-ones. Part 2: Stereodivergent synthesis of conformationally restricted analogues of β-homoserine

  摘要：

  Starting from the homochiral 3-1-butyldimethylsilyloxypyrrolidin-2-one 2, a stereodivergent synthetic route was developed leading to both 3,4-trans- and 3,4-cis-3-amino-4-hydroxymethyl pyrrolidin-2-ones, 19 and 28, that are conformationally restricted analogues of beta-homoserine 4. In addition, with a large number of 3,4-disubstituted pyrrolidin-2-ones in hand, a trend was observed for both H-3 chemical shifts and J(3,4) values, allowing the configuration to be assigned to either 3-hydroxy or 3-amino derivatives. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.03.003
• 作为产物：
  描述：

  (3S,4S,1'S)-3-tert-butyldimethylsilyloxy-4-methoxycarbonyl-1-(1'-phenylethyl)pyrrolidin-2-one 在 盐酸 、 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 (3S,4R,1'S)-4-benzoyloxymethyl-3-hydroxy-1-(1'-phenylethyl)pyrrolidin-2-one
  参考文献：
  名称：

  Chiral 3-hydroxypyrrolidin-2-ones. Part 2: Stereodivergent synthesis of conformationally restricted analogues of β-homoserine

  摘要：

  Starting from the homochiral 3-1-butyldimethylsilyloxypyrrolidin-2-one 2, a stereodivergent synthetic route was developed leading to both 3,4-trans- and 3,4-cis-3-amino-4-hydroxymethyl pyrrolidin-2-ones, 19 and 28, that are conformationally restricted analogues of beta-homoserine 4. In addition, with a large number of 3,4-disubstituted pyrrolidin-2-ones in hand, a trend was observed for both H-3 chemical shifts and J(3,4) values, allowing the configuration to be assigned to either 3-hydroxy or 3-amino derivatives. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.03.003