(2R,5R,6S,7R)-6-hydroxy-7-methyl-2-phenyl-3-oxa-1-azabicyclo[3.3.0]octan-8-one | 276696-80-1

• 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,5R,6S,7R)-6-hydroxy-7-methyl-2-phenyl-3-oxa-1-azabicyclo[3.3.0]octan-8-one
• 英文别名: (3R,6R,7S,7aR)-7-hydroxy-6-methyl-3-phenyl-3,6,7,7a-tetrahydro-1H-pyrrolo[1,2-c][1,3]oxazol-5-one
• CAS: 276696-80-1
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: KMFVVYIVWOVILU-GMTLJSCSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,5R,6S,7R)-6-hydroxy-7-methyl-2-phenyl-3-oxa-1-azabicyclo[3.3.0]octan-8-one 在 dimethyl sulfide borane 作用下， 生成 (2R,3S,4S)-1-benzyl-3-hydroxy-2-hydroxymethyl-4-methylpyrrolidine
  参考文献：
  名称：

  (2R,3S,4S)-3-Hydroxy-4-methyl-1-[(1S)-1-phenylethyl]pyrrolidine-2-methanol

  摘要：

  The crystal structure determination of the title compound, C14H21NO2, established the absolute configuration of the N-phenylethyl chain. The pyrrolidine ring adopts an envelope conformation. The 3-hydroxy and 2-hydroxymethyl groups are in pseudo-axial positions, while the the N-(l-phenylethyl) and 4-methyl groups are pseudo-equatorial.

  DOI：

  10.1107/s0108270194015027
• 作为产物：
  描述：

  bicyclic (2R,5R,6R)-6-hydroxy-2-phenyl-3-oxa-1-azabicyclo<3.3.0>octan-8-one 在 六甲基磷酰三胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 (2R,5R,6S,7R)-6-hydroxy-7-methyl-2-phenyl-3-oxa-1-azabicyclo[3.3.0]octan-8-one
  参考文献：
  名称：

  Diastereoselective Synthesis of (2S,3S,4S)-3-Hydroxy-4-methylproline, a Common Constituent of Several Antifungal Cyclopeptides

  摘要：

  (2S,3S,4S)-3-羟基-4-甲基脯氨酸2是从(S)-吡咯谷氨醇衍生而来的不饱和γ-内酰胺4和5合成的。从5开始，氢化过程中4-exo-甲基中间体的haplophilic效应提高了合成的对映选择性，收率为19%。© 2000 Elsevier Science Ltd. 保留所有权利。

  DOI：

  10.1016/s0040-4020(00)00117-4

文献信息

• Diastereoselective Synthesis of (2S,3S,4S)-3-Hydroxy-4-methylproline, a Common Constituent of Several Antifungal Cyclopeptides
  作者：Nicole Langlois、Felaniaina Rakotondradany

  DOI：10.1016/s0040-4020(00)00117-4

  日期：2000.4

  (2S,3S,4S)-3-Hydroxy-4-methylproline 2 was synthesized from unsaturated gamma-lactams 4 and 5 derived from (S)-pyroglutaminol. Starting from 5, haplophilic effect in the hydrogenation of a 4-exo-methylenic intermediate improved the diastereoselectivity of the synthesis, which was achieved in 19% yield. (C) 2000 Elsevier Science Ltd. All rights reserved.

  (2S,3S,4S)-3-羟基-4-甲基脯氨酸2是从(S)-吡咯谷氨醇衍生而来的不饱和γ-内酰胺4和5合成的。从5开始，氢化过程中4-exo-甲基中间体的haplophilic效应提高了合成的对映选择性，收率为19%。© 2000 Elsevier Science Ltd. 保留所有权利。
• (2R,3S,4S)-3-Hydroxy-4-methyl-1-[(1S)-1-phenylethyl]pyrrolidine-2-methanol
  作者：A. Chiaroni、C. Riche、L. Nicole

  DOI：10.1107/s0108270194015027

  日期：1995.9.15

  The crystal structure determination of the title compound, C14H21NO2, established the absolute configuration of the N-phenylethyl chain. The pyrrolidine ring adopts an envelope conformation. The 3-hydroxy and 2-hydroxymethyl groups are in pseudo-axial positions, while the the N-(l-phenylethyl) and 4-methyl groups are pseudo-equatorial.