(-)-(1S,4S,5S)-5-hydroxy-5-(2-methoxy-phenyl)bicyclo[2.2.1]heptan-2-one | 1053243-36-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (-)-(1S,4S,5S)-5-hydroxy-5-(2-methoxy-phenyl)bicyclo[2.2.1]heptan-2-one
• CAS: 1053243-36-9
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: ARXCUEFINWDGAU-BHDSKKPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.88
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (-)-(1S,4S,5S)-5-hydroxy-5-(2-methoxy-phenyl)bicyclo[2.2.1]heptan-2-one 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.25h， 以98%的产率得到(-)-(1S,2S,4S,5S)-2-(2-methoxyphenyl)bicyclo[2.2.1]heptane-2,5-diol
  参考文献：
  名称：

  Bicyclic diols and related derivatives as catalysts for the asymmetric diethylzinc addition to benzaldehyde

  摘要：

  Chiral bicyclic diols based on bicyclo[2.2.2]octane and bicyclo[2.2.1]heptane have been synthesized and their catalytic capacity in the asymmetric diethylzinc addition to benzaldehyde compared with those described for previously synthesized 2,6-bicyclo[2.2.2]octane-diols (BODOLs). The influence of the number of coordinating sites and the distance between them were studied. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.05.024
• 作为产物：
  描述：

  (-)-(1S,2S,4S,5R)-2-(2-methoxyphenyl)bicyclo[2.2.1]heptane-2,5-diol 在 N-甲基吲哚酮 、 四丙基高钌酸铵 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以85%的产率得到(-)-(1S,4S,5S)-5-hydroxy-5-(2-methoxy-phenyl)bicyclo[2.2.1]heptan-2-one
  参考文献：
  名称：

  Bicyclic diols and related derivatives as catalysts for the asymmetric diethylzinc addition to benzaldehyde

  摘要：

  Chiral bicyclic diols based on bicyclo[2.2.2]octane and bicyclo[2.2.1]heptane have been synthesized and their catalytic capacity in the asymmetric diethylzinc addition to benzaldehyde compared with those described for previously synthesized 2,6-bicyclo[2.2.2]octane-diols (BODOLs). The influence of the number of coordinating sites and the distance between them were studied. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.05.024

文献信息

• New bicyclic γ- and δ-aminoalcohols as catalysts for the asymmetric diethylzinc addition to benzaldehyde
  作者：Cecilia Olsson、Sara Helgesson、Torbjörn Frejd

  DOI：10.1016/j.tetasy.2008.06.002

  日期：2008.6

  A new class of chiral non-racemic γ- and δ-amino alcohols based on bicyclo[2.2.1]heptane and bicyclo[2.2.2]octane have been synthesized and used as catalysts in the asymmetric diethylzinc addition to benzaldehyde.

  合成了一种基于双环[2.2.1]庚烷和双环[2.2.2]辛烷的新型手性非外消旋γ-和δ-氨基醇，并用作苯甲醛不对称二乙基锌的催化剂。