(1R,2R,3R,4R,6R)-1-(benzyloxycarbonylamino)-2-hydroxy-3-iodobicyclo[2.2.2]octane-6-carboxylic acid | 1092566-99-8

• 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: (1R,2R,3R,4R,6R)-1-(benzyloxycarbonylamino)-2-hydroxy-3-iodobicyclo[2.2.2]octane-6-carboxylic acid
• 英文别名: (1R,2R,4R,5R,6R)-6-hydroxy-5-iodo-1-(phenylmethoxycarbonylamino)bicyclo[2.2.2]octane-2-carboxylic acid
• CAS: 1092566-99-8
• 化学式: C₁₇H₂₀INO₅
• 分子量: 445.254
• InChiKey: OFGOTICDPSOXQH-XKSGDERDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  95.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R,2R,3R,4R,6R)-1-(benzyloxycarbonylamino)-2-hydroxy-3-iodobicyclo[2.2.2]octane-6-carboxylic acid 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 以81%的产率得到(1R,2R,3S,4R,6R)-1-(benzyloxycarbonylamino)-2,3-epoxybicyclo[2.2.2]octane-6-carboxylic acid
  参考文献：
  名称：

  The iodolactone approach to enantiopure oxiranes of constrained chiral cyclic β-amino acids

  摘要：

  A simple and efficient method has been developed for the synthesis of enantiopure epoxide derivatives of some constrained chiral cyclic beta-amino acids via iodolactonization and alkaline de-iodation. Lower stereo-selectivities were observed when the classical method using mCPBA was used when a bicyclic beta-amino acid was involved leading to a quasi-inseparable mixture of two epoxides. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.09.005
• 作为产物：
  描述：

  (1R,2R,3R,6R,7R)-7-(benzyloxycarbonylamino)-2-iodo-4-oxa-8-tricyclo[4.3.1.0(3,7)]decan-5-one 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以98%的产率得到(1R,2R,3R,4R,6R)-1-(benzyloxycarbonylamino)-2-hydroxy-3-iodobicyclo[2.2.2]octane-6-carboxylic acid
  参考文献：
  名称：

  The iodolactone approach to enantiopure oxiranes of constrained chiral cyclic β-amino acids

  摘要：

  A simple and efficient method has been developed for the synthesis of enantiopure epoxide derivatives of some constrained chiral cyclic beta-amino acids via iodolactonization and alkaline de-iodation. Lower stereo-selectivities were observed when the classical method using mCPBA was used when a bicyclic beta-amino acid was involved leading to a quasi-inseparable mixture of two epoxides. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.09.005