4-[5-methyl-5-(3-methylhexa-3,5-dienyl)cyclopent-1-enyl]-4-oxobut-2-ynoic acid ethyl ester | 912356-58-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-[5-methyl-5-(3-methylhexa-3,5-dienyl)cyclopent-1-enyl]-4-oxobut-2-ynoic acid ethyl ester
• 英文别名: ethyl 4-[5-methyl-5-[(3E)-3-methylhexa-3,5-dienyl]cyclopenten-1-yl]-4-oxobut-2-ynoate
• CAS: 912356-58-2
• 化学式: C₁₉H₂₄O₃
• 分子量: 300.398
• InChiKey: LBVMHXWCPDKGNA-OVCLIPMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[5-methyl-5-(3-methylhexa-3,5-dienyl)cyclopent-1-enyl]-4-oxobut-2-ynoic acid ethyl ester 以 甲苯 为溶剂， 反应 24.0h， 以66%的产率得到8a,10a-dimethyl-4-oxo-1,2,4,6,8a,9,10,10a-octahydrobenzo[f]azulene-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthetic Study of 1,3-Butadiene-Based IMDA Approach to Construct a [5−7−6] Tricyclic Core and Its Application to the Total Synthesis of C8-epi-Guanacastepene O

  摘要：

  An efficient intramolecular Diels-Alder (IMDA) strategy for the construction of the [5-7-6] tricyclic core (18) of guanacastepenes has been developed from cis-and trans-1,3-butadiene-tethered-4-oxopent-2- ynoic acid ethyl esters 10 and 11. This method facilitates the synthesis of C8-epi-guanacastepene O (36) in a very efficient manner.

  DOI：

  10.1021/jo060996h
• 作为产物：
  描述：

  [5-Methyl-5-((E)-3-methyl-hexa-3,5-dienyl)-cyclopent-1-enyl]-methanol 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 碘苯二乙酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 13.5h， 生成 4-[5-methyl-5-(3-methylhexa-3,5-dienyl)cyclopent-1-enyl]-4-oxobut-2-ynoic acid ethyl ester
  参考文献：
  名称：

  Synthetic Study of 1,3-Butadiene-Based IMDA Approach to Construct a [5−7−6] Tricyclic Core and Its Application to the Total Synthesis of C8-epi-Guanacastepene O

  摘要：

  An efficient intramolecular Diels-Alder (IMDA) strategy for the construction of the [5-7-6] tricyclic core (18) of guanacastepenes has been developed from cis-and trans-1,3-butadiene-tethered-4-oxopent-2- ynoic acid ethyl esters 10 and 11. This method facilitates the synthesis of C8-epi-guanacastepene O (36) in a very efficient manner.

  DOI：

  10.1021/jo060996h

文献信息

• Synthetic Study of 1,3-Butadiene-Based IMDA Approach to Construct a [5−7−6] Tricyclic Core and Its Application to the Total Synthesis of C8-<i>e</i><i>pi</i>-Guanacastepene O
  作者：Chuang-Chuang Li、Cui-Hua Wang、Bo Liang、Xin-Hao Zhang、Lu-Jiang Deng、Shuang Liang、Jia-Hua Chen、Yun-Dong Wu、Zhen Yang

  DOI：10.1021/jo060996h

  日期：2006.9.1

  An efficient intramolecular Diels-Alder (IMDA) strategy for the construction of the [5-7-6] tricyclic core (18) of guanacastepenes has been developed from cis-and trans-1,3-butadiene-tethered-4-oxopent-2- ynoic acid ethyl esters 10 and 11. This method facilitates the synthesis of C8-epi-guanacastepene O (36) in a very efficient manner.