(4S)-2-bromo-4-hydroxy-4-methyl-3-[(2S)-1-oxo-1-pyrrolidin-1-ylpropan-2-yl]oxycyclohexa-2,5-dien-1-one | 1240408-32-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (4S)-2-bromo-4-hydroxy-4-methyl-3-[(2S)-1-oxo-1-pyrrolidin-1-ylpropan-2-yl]oxycyclohexa-2,5-dien-1-one
• CAS: 1240408-32-5
• 化学式: C₁₄H₁₈BrNO₄
• 分子量: 344.205
• InChiKey: BLNSPBUAFOURBS-XPTSAGLGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  四氢吡咯 、 C₁₀H₉BrO₄ 在 三甲基铝 、 水 、 rochelle salt 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 6.0h， 以68%的产率得到(4S)-2-bromo-4-hydroxy-4-methyl-3-[(2S)-1-oxo-1-pyrrolidin-1-ylpropan-2-yl]oxycyclohexa-2,5-dien-1-one
  参考文献：
  名称：

  Dearomatization applications of I(III) reagents and some unusual reactivity amongst resorcinol derived cyclohexadienones

  摘要：

  The oxidative dearomatization of resorcinol derivatives, which are outfitted with a lactic acid derived chiral tether, and mitigated by hypervalent iodine derivatives of PhIO, affords stable chiral cyclohexadienones as useful building blocks for the construction of many highly functionalized chiral six and seven-membered ring systems. Herein, we report a multitude of remarkable and unexpected diastereoselective transformations stemming from these cyclohexadienone adducts. Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2010.05.041

文献信息

• Dearomatization applications of I(III) reagents and some unusual reactivity amongst resorcinol derived cyclohexadienones
  作者：Todd A. Wenderski、Christophe Hoarau、Lupe Mejorado、Thomas R.R. Pettus

  DOI：10.1016/j.tet.2010.05.041

  日期：2010.7

  The oxidative dearomatization of resorcinol derivatives, which are outfitted with a lactic acid derived chiral tether, and mitigated by hypervalent iodine derivatives of PhIO, affords stable chiral cyclohexadienones as useful building blocks for the construction of many highly functionalized chiral six and seven-membered ring systems. Herein, we report a multitude of remarkable and unexpected diastereoselective transformations stemming from these cyclohexadienone adducts. Published by Elsevier Ltd.