(R,E)-3-(5-methylhex-2-enoyl)-4-phenyl-1,3-oxazolidine-2-one | 261896-46-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (R,E)-3-(5-methylhex-2-enoyl)-4-phenyl-1,3-oxazolidine-2-one
• 英文别名: 3-[(E)-3-isobutylpropenoyl]-4-(R)-phenyl-2-oxazolidinone；(4R)-3-[(E)-5-methylhex-2-enoyl]-4-phenyl-1,3-oxazolidin-2-one
• CAS: 261896-46-2
• 化学式: C₁₆H₁₉NO₃
• 分子量: 273.332
• InChiKey: IBWQYTSHAFLOTF-XYYIANASSA-N

物化性质

• 沸点：
  378.9±45.0 °C(predicted)
• 密度：
  1.142±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R,E)-3-(5-methylhex-2-enoyl)-4-phenyl-1,3-oxazolidine-2-one 在 lithium hydroxide 、 双氧水 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 1.0h， 生成 1-benzyl-4-(S)-isobutylpyrrolidine-3-(S)-carboxylic acid
  参考文献：
  名称：

  Synthesis of 4-alkyl-pyrrolidine-3-carboxylic acid stereoisomers

  摘要：

  All four possible stereoisomers of the 3-carboxyl-4-isopropyl-pyrrolidine (4) were prepared and their stereochemistry was assigned unambiguously. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00549-x
• 作为产物：
  描述：

  (2E)-5-甲基-2-己烯酸 在 草酰氯 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 2.0h， 生成 (R,E)-3-(5-methylhex-2-enoyl)-4-phenyl-1,3-oxazolidine-2-one
  参考文献：
  名称：

  Synthesis of 4-alkyl-pyrrolidine-3-carboxylic acid stereoisomers

  摘要：

  All four possible stereoisomers of the 3-carboxyl-4-isopropyl-pyrrolidine (4) were prepared and their stereochemistry was assigned unambiguously. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00549-x

文献信息

• Diasteroselective conjugate addition of diethylaluminum cyanide to a conjugated <i>N</i>-enoyl system: an alternative synthesis of (<i>S</i>)-pregabalin
  作者：Erika Tovar-Gudiño、Rosmarbel Morales-Nava、Mario Fernández-Zertuche

  DOI：10.1139/cjc-2013-0397

  日期：2014.1

  We have explored in this work the conjugate addition of diethylaluminum cyanide (Nagata’s reagent) to an N-enoyl system bearing the (R)-4-phenyl-2-oxazolidinone chiral auxiliary. Since this method provided a practical synthesis of γ-amino acids, we report the conjugate addition of diethylaluminum cyanide as the key step in the synthesis of (S)-pregabalin 1 in a five-step sequence of reactions from commercially available starting materials.

  在这项工作中，我们探讨了二乙基铝氰化物（Nagata试剂）对带有（R）-4-苯基-2-噁唑烷酮手性辅助基的N-烯酰系统的共轭加成。由于这种方法提供了γ-氨基酸的实用合成方法，因此我们报告了二乙基铝氰化物的共轭加成作为从商业起始材料进行的五步反应序列中合成（S）-pregabalin 1的关键步骤。
• BRANCHED ALKYL PYRROLIDINE-3-CARBOXYLIC ACIDS
  申请人：Warner-Lambert Company LLC

  公开号：EP1112253B1

  公开（公告）日：2004-10-20
• US6245801B1
  申请人：——

  公开号：US6245801B1

  公开（公告）日：2001-06-12
• [EN] BRANCHED ALKYL PYRROLIDINE-3-CARBOXYLIC ACIDS<br/>[FR] ACIDES PYRROLIDINE-3-CARBOXYLIQUES D'ALKYLE RAMIFIE
  申请人：WARNER LAMBERT CO

  公开号：WO2000015611A1

  公开（公告）日：2000-03-23

  Branched alkyl pyrrolidines of formula (I) are disclosed and are useful as agents in the treatment of epilepsy, faintness attacks, hypokinesia, cranial disorders, neurodegenerative disorders, depression, anxiety, panic, pain, and neuropathological disorders. Processes for the preparation and intermediates useful in the preparation are also disclosed.
• Synthesis of 4-alkyl-pyrrolidine-3-carboxylic acid stereoisomers
  作者：Rong Ling、I.Victor Ekhato、J.Ronald Rubin、David J Wustrow

  DOI：10.1016/s0040-4020(01)00549-x

  日期：2001.7

  All four possible stereoisomers of the 3-carboxyl-4-isopropyl-pyrrolidine (4) were prepared and their stereochemistry was assigned unambiguously. (C) 2001 Elsevier Science Ltd. All rights reserved.