(2R,3R,6R)-2-[[(1S,2S,4S)-2-bicyclo[2.2.1]hept-5-enyl]-hydroxymethyl]-6-methyl-3-prop-1-en-2-ylcyclohexan-1-one | 1188307-15-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2R,3R,6R)-2-[[(1S,2S,4S)-2-bicyclo[2.2.1]hept-5-enyl]-hydroxymethyl]-6-methyl-3-prop-1-en-2-ylcyclohexan-1-one
• CAS: 1188307-15-4
• 化学式: C₁₈H₂₆O₂
• 分子量: 274.403
• InChiKey: RDXICBYXQVUQSZ-GSPMIGDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  乙烯 、 (2R,3R,6R)-2-[[(1S,2S,4S)-2-bicyclo[2.2.1]hept-5-enyl]-hydroxymethyl]-6-methyl-3-prop-1-en-2-ylcyclohexan-1-one 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以100%的产率得到
  参考文献：
  名称：

  Expedient asymmetric synthesis of a functionalized 5-7-6 fused tricyclic skeleton present in caribenol A through ring opening-ring closing metathesis of a norbornene derivative

  摘要：

  A concise approach towards the synthesis of the highly biologically active terpenoid caribenol A is described involving sequential aldol condensation-ring opening-ring closing metathesis of a norbornene derivative. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.07.012
• 作为产物：
  描述：

  (+)-二氢香芹酮 、 (+/-)-endo-bicyclo[2.2.1]hept-5-ene-2-carbaldehyde 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 反应 0.25h， 以70%的产率得到(2R,3R,6R)-2-[[(1S,2S,4S)-2-bicyclo[2.2.1]hept-5-enyl]-hydroxymethyl]-6-methyl-3-prop-1-en-2-ylcyclohexan-1-one
  参考文献：
  名称：

  Expedient asymmetric synthesis of a functionalized 5-7-6 fused tricyclic skeleton present in caribenol A through ring opening-ring closing metathesis of a norbornene derivative

  摘要：

  A concise approach towards the synthesis of the highly biologically active terpenoid caribenol A is described involving sequential aldol condensation-ring opening-ring closing metathesis of a norbornene derivative. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.07.012

文献信息

• Expedient asymmetric synthesis of a functionalized 5-7-6 fused tricyclic skeleton present in caribenol A through ring opening-ring closing metathesis of a norbornene derivative
  作者：Sujit Mondal、Ram N. Yadav、Subrata Ghosh

  DOI：10.1016/j.tetlet.2009.07.012

  日期：2009.9

  A concise approach towards the synthesis of the highly biologically active terpenoid caribenol A is described involving sequential aldol condensation-ring opening-ring closing metathesis of a norbornene derivative. (c) 2009 Elsevier Ltd. All rights reserved.