(1'R,4R)-4-(1',5'-dimethylhex-4'-en-1'-yl)cyclohexa-1,5-diene-1-carboxylic acid | 1253784-46-1

• 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: (1'R,4R)-4-(1',5'-dimethylhex-4'-en-1'-yl)cyclohexa-1,5-diene-1-carboxylic acid
• 英文别名: (4R)-4-[(2R)-6-methylhept-5-en-2-yl]cyclohexa-1,5-diene-1-carboxylic acid
• CAS: 1253784-46-1
• 化学式: C₁₅H₂₂O₂
• 分子量: 234.338
• InChiKey: BPBBPEAZOQOIBE-CHWSQXEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  (1'R,4R)-4-(1',5'-dimethylhex-4'-en-1'-yl)cyclohexa-1,5-diene-1-carboxylic acid 、 trans-4-[(1E,3E)-1,5-dimethylhexa-1,3,5-trien-1-yl]cyclo-hexanecarboxylic acid 在 2-溴苯基硼酸 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以62%的产率得到
  参考文献：
  名称：

  Biomimetic Total Synthesis of Meiogynin A, an Inhibitor of Bcl-xL and Bak Interaction

  摘要：

  A short, convergent, and selective synthesis of meiogynin A, an inhibitor of the antiapoptotic protein Bcl-xL, has been performed. This synthesis, based on a biomimetic approach, allowed the determination of its absolute configuration. Three isomers of meiogynin A have also been elaborated. One of these was found to be three times more potent than the natural compound.

  DOI：

  10.1021/jo101088h
• 作为产物：
  描述：

  一氧化碳 、 在 potassium acetate 、 palladium diacetate 、 三苯基膦 、 水 、 sodium hydroxide 、 盐酸 作用下， 以 N,N-二甲基甲酰胺 、 水 为溶剂， 反应 2.0h， 以55 mg的产率得到(1'R,4R)-4-(1',5'-dimethylhex-4'-en-1'-yl)cyclohexa-1,5-diene-1-carboxylic acid
  参考文献：
  名称：

  Biomimetic Total Synthesis of Meiogynin A, an Inhibitor of Bcl-xL and Bak Interaction

  摘要：

  A short, convergent, and selective synthesis of meiogynin A, an inhibitor of the antiapoptotic protein Bcl-xL, has been performed. This synthesis, based on a biomimetic approach, allowed the determination of its absolute configuration. Three isomers of meiogynin A have also been elaborated. One of these was found to be three times more potent than the natural compound.

  DOI：

  10.1021/jo101088h

文献信息

• Selectivity in the Intermolecular Diels-Alder Reaction of Conjugated Trienes: Experimental and Theoretical Approaches
  作者：Camille Remeur、Sandy Desrat、Vincent Gandon、Fanny Roussi

  DOI：10.1002/ejoc.201800472

  日期：2018.11.15

  meiogynin A, an inhibitor of proteins of the Bcl‐2 family, have been elaborated by an intermolecular Diels–Alder (DA) reaction of various conjugated chloro‐trienes with two α,β‐unsaturated carboxylic acids as dienophiles. The perfect regioselectivity and good to excellent diastereoselectivities of these reactions were rationalized by DFT calculations.

  天然产物meiogynin A（Bcl-2家族蛋白的抑制剂）的十一种类似物通过各种共轭三氯乙烯与两种α，β-不饱和羧酸作为双亲亲代物的分子间狄尔斯-阿尔德（DA）反应而得到了完善。通过DFT计算合理化了这些反应的最佳区域选择性和良好至极好的非对映选择性。