(2R)-2-[(1S,2R,3S,4R)-3-(hydroxymethyl)-2-bicyclo[2.2.1]hept-5-enyl]hexan-2-ol | 528609-64-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R)-2-[(1S,2R,3S,4R)-3-(hydroxymethyl)-2-bicyclo[2.2.1]hept-5-enyl]hexan-2-ol
• CAS: 528609-64-5
• 化学式: C₁₄H₂₄O₂
• 分子量: 224.343
• InChiKey: IZISMWUEQCUCQN-MEBFFEOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R)-2-[(1S,2R,3S,4R)-3-(hydroxymethyl)-2-bicyclo[2.2.1]hept-5-enyl]hexan-2-ol 在 四丙基高钌酸铵 、 4 A molecular sieve 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 为溶剂， 以41%的产率得到(1R,2S,5R,6R,7S)-5-butyl-5-methyl-4-oxatricyclo[5.2.1.02,6]dec-8-en-3-one
  参考文献：
  名称：

  Enantiodivergent syntheses of γ-substituted butenolides with tertiary and quaternary asymmetric centers

  摘要：

  Continuous nucleophilic addition with several organometallic reagents to tricyclic lactone (-)-1 proceeded diastereoselectively. Newly generated tertiary and quaternary asymmetric centers were controlled by the order in which the nucleophilic reagents were added. Using this methodology, enantiodivergent syntheses of several gamma-substituted butenolides with tertiary and quaternary asymmetric centers were established from a single chiral material. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02711-9
• 作为产物：
  描述：

  正丁基锂 、 甲基溴化镁 、 (1SR,2RS,6SR,7RS)-4-oxatricyclo[5.2.1.0^2,6]dec-8-en-3-one 以 甲苯 为溶剂， 以60%的产率得到(2R)-2-[(1S,2R,3S,4R)-3-(hydroxymethyl)-2-bicyclo[2.2.1]hept-5-enyl]hexan-2-ol
  参考文献：
  名称：

  Enantiodivergent syntheses of γ-substituted butenolides with tertiary and quaternary asymmetric centers

  摘要：

  Continuous nucleophilic addition with several organometallic reagents to tricyclic lactone (-)-1 proceeded diastereoselectively. Newly generated tertiary and quaternary asymmetric centers were controlled by the order in which the nucleophilic reagents were added. Using this methodology, enantiodivergent syntheses of several gamma-substituted butenolides with tertiary and quaternary asymmetric centers were established from a single chiral material. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02711-9

文献信息

• Enantiodivergent syntheses of γ-substituted butenolides with tertiary and quaternary asymmetric centers
  作者：Katsufumi Suzuki、Kohei Inomata

  DOI：10.1016/s0040-4039(02)02711-9

  日期：2003.1

  Continuous nucleophilic addition with several organometallic reagents to tricyclic lactone (-)-1 proceeded diastereoselectively. Newly generated tertiary and quaternary asymmetric centers were controlled by the order in which the nucleophilic reagents were added. Using this methodology, enantiodivergent syntheses of several gamma-substituted butenolides with tertiary and quaternary asymmetric centers were established from a single chiral material. (C) 2003 Elsevier Science Ltd. All rights reserved.