5-Ethoxy-9-<2.2.6-trimethyl-cyclohexen-(6)-yl>-3.7-dimethyl-nonatrien-(2.6.8)-al-1 | 89553-27-5

• 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: 5-Ethoxy-9-<2.2.6-trimethyl-cyclohexen-(6)-yl>-3.7-dimethyl-nonatrien-(2.6.8)-al-1
• 英文别名: (2E,6E,8E)-5-ethoxy-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,6,8-trienal
• CAS: 89553-27-5
• 化学式: C₂₂H₃₄O₂
• 分子量: 330.511
• InChiKey: LBAQHAOBTRJXLH-QNAIFCEVSA-N

物化性质

• 沸点：
  451.9±45.0 °C(Predicted)
• 密度：
  0.955±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

文献信息

• Manufacture of retinoids
  申请人：Radspieler Alexander

  公开号：US20050014976A1

  公开（公告）日：2005-01-20

  A process for the manufacture of retinal (I) comprises reacting a 5-(2,6,6-trimethyl-cyclohex-1-enyl)-1,4-pentadiene derivative (IIa) or a 5-(2,6,6-trimethyl-cyclohex-2-enyl)-1,4-pentadiene derivative (IIb) or a 5-(2,6,6-trimethyl-2-cyclohexen-1-ylidene)-1-pentene derivative (IIc) or a 5-(2,6,6-trimethyl-cyclohex-1-enyl)-penta-1-en-4-yne derivative (IId) or a 5-(2,6,6-trimethyl-cyclohex-2-enyl)-penta-1-en-4-yne derivative (IIe) with a 1,3-butadiene derivative H2C═C(CH3)CCH═CHOR4 (III) in the presence of a Lewis or Brönsted acid and subjecting the compound obtained in each case [(IVa), (IVb), (IVc), (IVd) or (IVe), respectively] to basic or acidic conditions to eliminate therefrom the moiety R2H and thus produce, according to the immediate precursor, retinal itself or a particular derivative thereof [(I′), (I′), (Va) or (Vb), respectively] and, where in two cases such derivative is produced featuring a triple bond [derivative (Va) or (Vb)], hydrogenating this to produce retinal (I) or the derivative (I′), respectively, and each case where a derivative (I′) or (I′) has been produced, isomerizing this under basic or acidic conditions or in the presence of a metal catalyst to the desired retinal (I). The so-produced retinal is usually in the form of an isomeric mixture, normally as (9 E/Z, 13 E/Z)-retinal, and this can be isomerized according to a further inventive aspect to (all-E)-retinal by the acid-catalysed formation of an adduct of (all-E)-retinal with hydroquinone in crystalline form. The so obtained (all-E)-retinal-hydroquinone adduct can then if desired be converted to vitamin A alcohol in the predominantly (all-E)-isomeric form by a method known per se. The novel starting materials (IIa), (IIb), (IIc), (IVI) and (IIe) represent a still further inventive aspect. Retinal is a valuable intermediate in the synthesis of further vitamin A compounds (retinoids). The retinoids, particularly vitamin A alcohol (retinol), are known to be valuable substances which promote the well-being of humans, inter alia in respect of vision, the immune system and growth, and for this reason are often used as components of multivitamin preparations and as additives for certain food- and feedstuffs.

  制备视黄醛（I）的过程包括在路易斯或布朗斯特酸的存在下，将5-（2,6,6-三甲基环己-1-烯基）-1,4-戊二烯衍生物（IIa）或5-（2,6,6-三甲基环己-2-烯基）-1,4-戊二烯衍生物（IIb）或5-（2,6,6-三甲基-2-环己烯-1-基）-1-戊烯衍生物（IIc）或5-（2,6,6-三甲基环己-1-烯基）-戊-1-烯-4-炔衍生物（IId）或5-（2,6,6-三甲基环己-2-烯基）-戊-1-烯-4-炔衍生物（IIe）与1,3-丁二烯衍生物H2C═C（CH3）CCH═CHOR4（III）反应，并在每种情况下得到的化合物[(IVa)，(IVb)，(IVc)，(IVd)或(IVe)，分别]在酸性或碱性条件下消除其R2H基团，从而根据直接前体制备视黄醛本身或特定衍生物[(I′)，(I′)，(Va)或(Vb)，分别]，在两种情况下产生带有三键的衍生物[(Va)或(Vb)]，将其加氢以产生视黄醛（I）或其衍生物（I′），并在每种情况下，产生衍生物（I′）或（I′）后，在碱性或酸性条件下或在金属催化剂的存在下使其异构化为所需的视黄醛（I）。所生产的视黄醛通常是以异构混合物的形式存在，通常为（9 E/Z，13 E/Z）-视黄醛，可以根据进一步的发明方面将其异构化为（全E）-视黄醛，方法是在晶体形式下通过酸催化形成（全E）-视黄醛与对苯二酚的加合物。然后，如有需要，可以将所获得的（全E）-视黄醛-对苯二酚加合物转化为主要为（全E）-异构体的维生素A醇，这是一种已知的方法。新的起始材料（IIa），（IIb），（IIc），（IVI）和（IIe）代表了另一个创新方面。视黄醛是合成进一步维生素A化合物（视黄醇类）的有价值中间体。视黄醇类，特别是维生素A醇，已知是有价值的物质，可以促进人类的健康，包括视力，免疫系统和生长等方面，并因此经常用作多种维生素制剂的组分和某些食品和饲料的添加剂。
• MANUFACTURE OF RETINOIDS
  申请人：DSM IP Assets B.V.

  公开号：EP1442014B1

  公开（公告）日：2007-03-21
• US7067703B2
  申请人：——

  公开号：US7067703B2

  公开（公告）日：2006-06-27