(1S)-1-[(1S,2R,3S,4R)-3-(hydroxymethyl)-2-bicyclo[2.2.1]hept-5-enyl]ethanol | 528609-57-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S)-1-[(1S,2R,3S,4R)-3-(hydroxymethyl)-2-bicyclo[2.2.1]hept-5-enyl]ethanol
• CAS: 528609-57-6
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: GGOXZOIAIGTWBD-GENCIFFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  (1S)-1-[(1S,2R,3S,4R)-3-(hydroxymethyl)-2-bicyclo[2.2.1]hept-5-enyl]ethanol 在 四丙基高钌酸铵 、 4 Angstroem MS 、 N-甲基吗啉氧化物 、 邻二氯苯 作用下， 以 二氯甲烷 为溶剂， 生成 (S)-(+)-β-angelica lactone
  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：

  (1R,2S,3R,4S)-3-Acetyl-bicyclo[2.2.1]hept-5-ene-2-carbaldehyde 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以76%的产率得到(R)-1-((1S,2R,3S,4R)-3-Hydroxymethyl-bicyclo[2.2.1]hept-5-en-2-yl)-ethanol
  参考文献：
  名称：

  Synthesis of 3,11-Dioxatetracyclo[6.3.0.0^2,6.0^5,9]undecanes and 3,5,7-Trioxapentacyclo[7.2.1.0^2,8.0^4,11.0^6,10]dodecane

  摘要：

  AbstractThe synthesis of 3,11‐dioxatetracyclo[6.3.0.02,6.05,9]undecanes has been accomplished from furans in a short sequence by iodine‐induced cyclization reaction. The application of iodine‐induced cyclization reaction for the synthesis of 3,5,7‐trioxapentacyclo[7.2.1.02,8.04,11.06,10]dodecane itself was also demonstrated.

  DOI：

  10.1002/jccs.199700094

文献信息

• Synthesis of 3,11-Dioxatetracyclo[6.3.0.0^2,6.0^5,9]undecanes and 3,5,7-Trioxapentacyclo[7.2.1.0^2,8.0^4,11.0^6,10]dodecane
  作者：Hui-Chang Lin、Chung-Yi Wu、Hsien-Jen Wu

  DOI：10.1002/jccs.199700094

  日期：1997.12

  AbstractThe synthesis of 3,11‐dioxatetracyclo[6.3.0.02,6.05,9]undecanes has been accomplished from furans in a short sequence by iodine‐induced cyclization reaction. The application of iodine‐induced cyclization reaction for the synthesis of 3,5,7‐trioxapentacyclo[7.2.1.02,8.04,11.06,10]dodecane itself was also demonstrated.
• 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.