(+/-)-(1R,2S,6S)-2-[(benzyloxy)methyl]-1,6-dimethylcyclohex-3-ene-1-carbaldehyde

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+/-)-(1R,2S,6S)-2-[(benzyloxy)methyl]-1,6-dimethylcyclohex-3-ene-1-carbaldehyde
• 英文别名: (1R,2S,6S)-1,6-dimethyl-2-(phenylmethoxymethyl)cyclohex-3-ene-1-carbaldehyde
• 化学式: C₁₇H₂₂O₂
• 分子量: 258.36
• InChiKey: HBYONTOWROTCMM-USXIJHARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+/-)-(1R,2S,6S)-2-[(benzyloxy)methyl]-1,6-dimethylcyclohex-3-ene-1-carbaldehyde 在 palladium on activated charcoal lithium aluminium tetrahydride 、 碘代三甲硅烷 、 氢气 作用下， 以 四氢呋喃 、 乙醇 、 氯仿 为溶剂， 20.0 ℃ 、405.3 kPa 条件下， 反应 125.0h， 生成 (+/-)-(1R,2S,6S)-1,2-bis(iodomethyl)-1,6-dimethylcyclohexane
  参考文献：
  名称：

  Core Structure of Eremophilanes and Bakkanes through Niobium Catalyzed Diels−Alder Reaction:  Synthesis of (±)-Bakkenolide A

  摘要：

  A suitable intermediate for the synthesis of eremophilanes and bakkanes was prepared by a highly regioselective and stereoselective one-step synthesis through a niobium catalyzed Diels-Alder reaction. As a demonstration of the versatility of this intermediate, a total synthesis of (+)-bakkenolide A is described.

  DOI：

  10.1021/jo061722x
• 作为产物：
  描述：

  2,4-戊二烯酸 在 niobium pentachloride lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 92.0h， 生成 (+/-)-(1R,2S,6S)-2-[(benzyloxy)methyl]-1,6-dimethylcyclohex-3-ene-1-carbaldehyde
  参考文献：
  名称：

  Core Structure of Eremophilanes and Bakkanes through Niobium Catalyzed Diels−Alder Reaction:  Synthesis of (±)-Bakkenolide A

  摘要：

  A suitable intermediate for the synthesis of eremophilanes and bakkanes was prepared by a highly regioselective and stereoselective one-step synthesis through a niobium catalyzed Diels-Alder reaction. As a demonstration of the versatility of this intermediate, a total synthesis of (+)-bakkenolide A is described.

  DOI：

  10.1021/jo061722x

文献信息

• Core Structure of Eremophilanes and Bakkanes through Niobium Catalyzed Diels−Alder Reaction:  Synthesis of (±)-Bakkenolide A
  作者：Mauricio G. Constantino、Kleber T. de Oliveira、Ellen C. Polo、Gil V. J. da Silva、Timothy J. Brocksom

  DOI：10.1021/jo061722x

  日期：2006.12.1

  A suitable intermediate for the synthesis of eremophilanes and bakkanes was prepared by a highly regioselective and stereoselective one-step synthesis through a niobium catalyzed Diels-Alder reaction. As a demonstration of the versatility of this intermediate, a total synthesis of (+)-bakkenolide A is described.