(2Z,4E)-3-Methyl-5-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)penta-2,4-dien-1-al | 25528-88-5

• 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: (2Z,4E)-3-Methyl-5-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)penta-2,4-dien-1-al
• 英文别名: 9-cis-Dehydro-β-ionylidenacetaldehyd；(2Z,4E)-3-methyl-5-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)penta-2,4-dienal
• CAS: 25528-88-5
• 化学式: C₁₅H₂₀O
• 分子量: 216.323
• InChiKey: OJHSBMRFBRXYNM-GHYOLMRSSA-N

物化性质

• 沸点：
  334.2±11.0 °C(Predicted)
• 密度：
  0.967±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2Z,4E)-3-Methyl-5-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)penta-2,4-dien-1-al 在 lithium aluminium tetrahydride 、 potassium carbonate 作用下， 生成 9-cis-Vitamin A(2)
  参考文献：
  名称：

  维生素A 2-合成中的合成物。2. Mitteilung。Die Darstellung von Vier sterisch ungehinderten Vitamin-A 2 -Isomeren

  摘要：

  由顺式和反式-脱氢-β制备了四种结晶的维生素A 2异构体，即全反式，13-顺式，9-顺式和9,13-二顺式，以及相应的酸和醛-亚乙炔基乙醛。

  DOI：

  10.1002/hlca.19620450216
• 作为产物：
  描述：

  3-甲基-2-丁烯酸乙酯 在 盐酸 二异丁基氢化铝 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 0.75h， 生成 (2Z,4E)-3-Methyl-5-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)penta-2,4-dien-1-al
  参考文献：
  名称：

  Syntheses of High Specific Activity 2,3- and 3,4-[3H]2-9-cis-Retinoic Acid

  摘要：

  B-cis-Retinoic acid (9-cis-RA) is an endogenous hormone which binds and activates the retinoic acid receptors (RARs) and the retinoic X receptors (RXRs). In order to investigate the function of 9-cis-RA in vitro and in vivo high specific activity labeled 9-cis-RA was prepared. Two tritium labels were efficiently introduced at the 2,3- or 3,4-positions, respectively, in the cyclohexene ring moiety resulting in labeled 9-cis-RA with specific activity of 58-60 Ci/mmol. The critical ring-labeling step relies on a highly regioselective tritiation of either a terminal or an isolated double bond in the presence of the conjugated retinoate side chain. Moreover, the labeling is performed at the penultimate synthetic step resulting in optimization of radiochemical yields and ease of synthesis. This is the first reported synthesis of ring-labeled [H-3](2)-9-cis-RA, and the methodology described herein is applicable to the synthesis of other retinoic acid isomers.

  DOI：

  10.1021/jo00110a023

文献信息

• Methods for stereospecific synthesis of polyene aldehydes
  申请人：Ligand Pharmaceuticals Incorporated

  公开号：US05567855A1

  公开（公告）日：1996-10-22

  Methods for stereospecific synthesis of 9-cis olefins and retinoids. In one particular aspect, a cis olefin is generated via a lactol ring opening with complete retention of double bond configuration.

  9-顺式烯烃和视黄醇的立体专一合成方法。在一个特定的方面，通过内酯环开启生成顺式烯烃，且双键构型完全保留。
• Olive; Mousseron-Canet, Bulletin de la Societe Chimique de France, 1969, vol. 9, p. 3252 - 3257
  作者：Olive、Mousseron-Canet

  DOI：——

  日期：——
• J. Org. Chem. 1995, 60, 1195-1200
  作者：

  DOI：——

  日期：——
• Syntheses of High Specific Activity 2,3- and 3,4-[3H]2-9-cis-Retinoic Acid
  作者：Youssef L. Bennani、Marcus F. Boehm

  DOI：10.1021/jo00110a023

  日期：1995.3

  B-cis-Retinoic acid (9-cis-RA) is an endogenous hormone which binds and activates the retinoic acid receptors (RARs) and the retinoic X receptors (RXRs). In order to investigate the function of 9-cis-RA in vitro and in vivo high specific activity labeled 9-cis-RA was prepared. Two tritium labels were efficiently introduced at the 2,3- or 3,4-positions, respectively, in the cyclohexene ring moiety resulting in labeled 9-cis-RA with specific activity of 58-60 Ci/mmol. The critical ring-labeling step relies on a highly regioselective tritiation of either a terminal or an isolated double bond in the presence of the conjugated retinoate side chain. Moreover, the labeling is performed at the penultimate synthetic step resulting in optimization of radiochemical yields and ease of synthesis. This is the first reported synthesis of ring-labeled [H-3](2)-9-cis-RA, and the methodology described herein is applicable to the synthesis of other retinoic acid isomers.
• Synthesen in der Vitamin-A₂-Reihe. 2. Mitteilung. Die Darstellung von vier sterisch ungehinderten Vitamin-A₂-Isomeren
  作者：U. Schwieter、C. V. Planta、R. Rüegg、O. Isler

  DOI：10.1002/hlca.19620450216

  日期：——

  Four crystalline vitamin A2 isomers, i.e. all-trans, 13-cis, 9-cis, and 9,13-di-cis, as well as the corresponding acids and aldehydes, have been prepared from cis- and trans-dehydro-β-ionylideneacetaldehyde.

  由顺式和反式-脱氢-β制备了四种结晶的维生素A 2异构体，即全反式，13-顺式，9-顺式和9,13-二顺式，以及相应的酸和醛-亚乙炔基乙醛。