4,6-dimethyl-6-[(E)-2-(2,6,6-trimethylcyclohexen-1-yl)ethenyl]cyclohexa-1,3-diene-1-carbaldehyde | 137046-92-5

• 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: 4,6-dimethyl-6-[(E)-2-(2,6,6-trimethylcyclohexen-1-yl)ethenyl]cyclohexa-1,3-diene-1-carbaldehyde
• CAS: 137046-92-5
• 化学式: C₂₀H₂₈O
• 分子量: 284.442
• InChiKey: YNMMZWRTISCJJG-ZRDIBKRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (7E,9E)-beta-离子亚基乙醛 、 (E)-trimethyl((3-methylbuta-1,3-dien-1-yl)oxy)silane 在 potassium tert-butylate 作用下， 生成 4,6-dimethyl-6-[(E)-2-(2,6,6-trimethylcyclohexen-1-yl)ethenyl]cyclohexa-1,3-diene-1-carbaldehyde
  参考文献：
  名称：

  Regioselective addition of the prenal potassium dienolate onto α,β-unsaturated aldehydes. A short access to polyenaldehydes

  摘要：

  The potassium dienolate of prenal obtained by treatment of the corresponding dienoxysilane with tBuOK was reacted with enaldehydes. In all cases a gamma-specific reaction occurs. According to the reaction conditions gamma;1,2 or a gamma;1,4 coupled product was selectively obtained with enals. The gamma;1,2 reaction provided an efficient prenylation procedure. A short two-step synthesis of retinal is described. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01544-5

文献信息

• A new prenylation method using the lithium enolate of prenal. Reaction with polyunsaturated aldehydes. A short access to retinal.
  作者：Lucette Duhamel、Jerôme Guillemont、Jean-Marie Poirier、Pierre Chabardes

  DOI：10.1016/0040-4039(91)80022-x

  日期：1991.1

  The enolate of prenal 1 prepared from the corresponding silyl enol ether 2 or enol acetate 3 led to a γ-regiospecific reaction with polyunsaturated aldehydes 4 yielding dihydropyrans 5 leading after hydrolysis to polyenals 7. This process allows the introduction of the isoprenyl skeleton. A synthesis of retinal. from β-ionylidenacetaldehyde is reported.

  由相应的甲硅烷基烯醇醚2或烯醇乙酸酯3制备的醛1的烯醇化物与多不饱和醛4发生γ-区域特异性反应，生成二氢吡喃5，水解后生成多烯醛7。该过程允许引入异戊二烯基骨架。视网膜的合成。据报道来自β-离子基乙醛。