(R)-3-[(R)-2-methylhex-5-en-3-yl]-4-phenyloxazolidin-2-one | 434307-00-3

• 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)-3-[(R)-2-methylhex-5-en-3-yl]-4-phenyloxazolidin-2-one
• 英文别名: (4R)-3-[(3R)-2-methylhex-5-en-3-yl]-4-phenyl-1,3-oxazolidin-2-one
• CAS: 434307-00-3
• 化学式: C₁₆H₂₁NO₂
• 分子量: 259.348
• InChiKey: VMGVANBNNWLTCI-CABCVRRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-3-[(R)-2-methylhex-5-en-3-yl]-4-phenyloxazolidin-2-one 在 正丁基锂 、 二氯二茂锆 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 (3R,5R)-1-[(R)-2-hydroxy-1-phenylethyl]-5-isopropyl-3-methylpyrrolidin-2-one 、 (3S,5R)-1-[(R)-2-hydroxy-1-phenylethyl]-5-isopropyl-3-methylpyrrolidin-2-one
  参考文献：
  名称：

  Asymmetric synthesis of di- and trisubstituted pyrrolidinones via zirconium-mediated intramolecular coupling of N-3-alkenyl carbamates

  摘要：

  N-3-Alkenyl carbamates, which are readily available in enantiomerically pure form, undergo a stereoselective intramolecular coupling under the effect of a Cp2ZrCl2/2n-BuLi reagent. The influence of the carbamate structure on the stereoselectivity was tested. The reaction gives an easy access to various di-and trisubstituted enantiopure pyrrolidinones. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.01.026
• 作为产物：
  描述：

  (R)-2-[2-Methyl-prop-(E)-ylideneamino]-2-phenyl-ethanol 在 吡啶 、 4-二甲氨基吡啶 、 cerium(III) chloride 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 (R)-3-[(R)-2-methylhex-5-en-3-yl]-4-phenyloxazolidin-2-one
  参考文献：
  名称：

  Asymmetric synthesis of di- and trisubstituted pyrrolidinones via zirconium-mediated intramolecular coupling of N-3-alkenyl carbamates

  摘要：

  N-3-Alkenyl carbamates, which are readily available in enantiomerically pure form, undergo a stereoselective intramolecular coupling under the effect of a Cp2ZrCl2/2n-BuLi reagent. The influence of the carbamate structure on the stereoselectivity was tested. The reaction gives an easy access to various di-and trisubstituted enantiopure pyrrolidinones. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.01.026

文献信息

• Asymmetric synthesis of di- and trisubstituted pyrrolidinones via zirconium-mediated intramolecular coupling of N-3-alkenyl carbamates
  作者：Clément Denhez、Jean-Luc Vasse、Dominique Harakat、Jan Szymoniak

  DOI：10.1016/j.tetasy.2007.01.026

  日期：2007.2

  N-3-Alkenyl carbamates, which are readily available in enantiomerically pure form, undergo a stereoselective intramolecular coupling under the effect of a Cp2ZrCl2/2n-BuLi reagent. The influence of the carbamate structure on the stereoselectivity was tested. The reaction gives an easy access to various di-and trisubstituted enantiopure pyrrolidinones. (c) 2007 Elsevier Ltd. All rights reserved.