11-顺式-3,4-二去氢视黄醛 | 41470-05-7

• 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
• 中文名称: 11-顺式-3,4-二去氢视黄醛
• 英文名称: 11-cis-3-dehydroretinal
• 英文别名: 11-cis-Vitamin-A(2)-aldehyd；(2E,4Z,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)nona-2,4,6,8-tetraenal
• CAS: 41470-05-7
• 化学式: C₂₀H₂₆O
• 分子量: 282.426
• InChiKey: QHNVWXUULMZJKD-IOUUIBBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.35
• 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：

  (2E,4Z,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-2,4,6,8-nonatetraenenitrile 在 二异丁基氢化铝 、 水 、 silica gel 作用下， 以 正己烷 为溶剂， 反应 2.0h， 以75%的产率得到11-顺式-3,4-二去氢视黄醛
  参考文献：
  名称：

  A Convenient and Stereoselective Synthesis of 11Z-3,4-Didehydroretinal by Horner-Emmons Reaction Using Diphenyl Phosphonate

  摘要：

  开发出了一种简便的 3,4-二脱氢视黄醛合成方法。在冠醚存在下，3,4-二脱氢-β-酮与膦酸二苯酯发生 Horner-Emmons 反应，生成视黄腈异构混合物，其中新生成的双键主要为 11Z 形式。在分离出 11Z 形式的视黄醛腈后，可以将其转化为相应的视黄醛，且收率很高，不会发生双键异构化。

  DOI：

  10.1248/cpb.56.112

文献信息

• Synthesen in der Vitamin-A₂-Reihe. 1. Mitteilung. Die Darstellung von kristallinem all-<i>trans</i>-Vitamin A₂und von zwei Isomeren mit sterischer Hinderung
  作者：U. Schwieter、G. Saucy、M. Montavon、C. v. Planta、R. Rüegg、O. Isler

  DOI：10.1002/hlca.19620450215

  日期：——

  Crystalline all-trans-vitamin A2 has been prepared from dehydro-β-C14-aldehyde and the isomeric 3-methyl-pent-2-en-4-yn-1-ols. Two vitamin A2 isomers with Pauling hindrance (11-cis and 11, 13-di-cis) have been synthesized from the same starting materials.

  结晶清一色反式-维生素阿2已经从脱氢-β-C制备的14 -醛和异构的3-甲基戊-2-烯-4-炔-1-醇。从相同的原料合成了具有鲍林阻碍的两种维生素A 2异构体（11-顺式和11- 13-顺式）。
• TOPICAL PAIN FORMULATION
  申请人：Bennett Gary Dean

  公开号：US20110052738A1

  公开（公告）日：2011-03-03

  A topical pain formulation, comprising one or more analgesic compounds and a plurality of skin penetrants.
• RED-SHIFTED CHANNELRHODOPSINS
  申请人：SPUDICH John Lee

  公开号：US20130066047A1

  公开（公告）日：2013-03-14

  Methods and compositions are used to identify and characterize new channelrhodopsins derived from algae and several of which are red-shifted. The rhodopsin domain of these red-shifted channelrhodopsins can be cloned and expressed in mammalian systems and used in optogenetic applications and as therapeutic agents. Also provided are methods and compositions for use in red-shifting the absorbance maxima of channelrhodopsins in order to improve their utility for use in vivo.
• cDNA-DERIVED NUCLEIC ACIDS ENCODING RED-SHIFTED CHANNELRHODOPSINS
  申请人：Board of Regents of the University of Texas System

  公开号：US20140135382A1

  公开（公告）日：2014-05-15

  Methods and compositions are used to identify and characterize new channelrhodopsins derived from algae and several of which are red-shifted. The rhodopsin domain of these red-shifted channelrhodopsins can be cloned and expressed in mammalian systems and used in optogenetic applications and as therapeutic agents. Also provided are methods and compositions for use in red-shifting the absorbance maxima of channelrhodopsins in order to improve their utility for use in vivo.
• US8580937B2
  申请人：——

  公开号：US8580937B2

  公开（公告）日：2013-11-12