[4-[(2S,3R,4S,5S)-5-(1,3-benzodioxol-5-yl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenyl] benzoate | 1310802-74-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: [4-[(2S,3R,4S,5S)-5-(1,3-benzodioxol-5-yl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenyl] benzoate
• CAS: 1310802-74-4
• 化学式: C₂₇H₂₆O₆
• 分子量: 446.5
• InChiKey: MBQYMJCTTUTZER-ZSMYEMOWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [4-[(2S,3R,4S,5S)-5-(1,3-benzodioxol-5-yl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenyl] benzoate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以56%的产率得到chicanine
  参考文献：
  名称：

  Asymmetric synthesis of (−)-chicanine using a highly regioselective intramolecular Mitsunobu reaction and revision of its absolute configuration

  摘要：

  First asymmetric synthesis of (-)-chicanine has been accomplished in 14 steps by employing the Evans asymmetric syn-selective aldol reaction, diastereoselective hydroboration and an regioselective, intramolecular Mitsunobu etherification. The absolute configuration of (+)- and ()-chicanine has been revised to 2R,3S,4R,5R and 2S,3R,4S,5S, respectively, through CD analysis. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.03.154
• 作为产物：
  描述：

  在 四丁基氟化铵 、 氰基亚甲基三甲基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 40.0h， 生成 、 [4-[(2S,3R,4S,5S)-5-(1,3-benzodioxol-5-yl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenyl] benzoate
  参考文献：
  名称：

  Asymmetric synthesis of (−)-chicanine using a highly regioselective intramolecular Mitsunobu reaction and revision of its absolute configuration

  摘要：

  First asymmetric synthesis of (-)-chicanine has been accomplished in 14 steps by employing the Evans asymmetric syn-selective aldol reaction, diastereoselective hydroboration and an regioselective, intramolecular Mitsunobu etherification. The absolute configuration of (+)- and ()-chicanine has been revised to 2R,3S,4R,5R and 2S,3R,4S,5S, respectively, through CD analysis. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.03.154