3-methyl-5-(2,6,6ptrimethyl-1-cyclohexenyl)-1,5-dibenzenesulfonyl-2-pentene | 433702-96-6

• 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: 3-methyl-5-(2,6,6ptrimethyl-1-cyclohexenyl)-1,5-dibenzenesulfonyl-2-pentene
• 英文别名: [(E)-5-(benzenesulfonyl)-3-methyl-5-(2,6,6-trimethylcyclohexen-1-yl)pent-2-enyl]sulfonylbenzene
• CAS: 433702-96-6
• 化学式: C₂₇H₃₄O₄S₂
• 分子量: 486.697
• InChiKey: AQQPCXLZPRKBML-HEHNFIMWSA-N

物化性质

• 沸点：
  661.6±55.0 °C(Predicted)
• 密度：
  1.154±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  85
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-methyl-5-(2,6,6ptrimethyl-1-cyclohexenyl)-1,5-dibenzenesulfonyl-2-pentene 在 sodium hydroxide 、 potassium tert-butylate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 维生素 A 醋酸酯
  参考文献：
  名称：

  General and systematic synthetic entry to carotenoid natural products

  摘要：

  DOI：

  10.1016/j.tet.2004.09.002
• 作为产物：
  描述：

  {[(2,6,6-trimethyl-1-cyclohexen-1-yl)methyl]sulfonyl}benzene 在 正丁基锂 、 LiNbMoO₆ 、 双氧水 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 苯 为溶剂， 反应 8.5h， 生成 3-methyl-5-(2,6,6ptrimethyl-1-cyclohexenyl)-1,5-dibenzenesulfonyl-2-pentene
  参考文献：
  名称：

  General and systematic synthetic entry to carotenoid natural products

  摘要：

  DOI：

  10.1016/j.tet.2004.09.002

文献信息

• [EN] PRACTICAL AND EFFICIENT SYNTHETIC METHOD OF RETINOIC ACID AND ITS DERIVATIVES<br/>[FR] METHODE DE SYNTHESE PRATIQUE ET EFFICACE DE L'ACIDE RETINOIQUE ET DE SES DERIVES
  申请人：KOO SANGHO

  公开号：WO2002044140A1

  公开（公告）日：2002-06-06

  The present invention provides allylic disulfone of Chemical Formula 1, an important intermediate which can be used for syntheses of retinoids and carotenoids, a process for preparing the same, and a process for preparing retinoid compounds by using the said intermediate, and, in particular, a process for preparing retinoic acid of Chemical Formula 2 and alkyl retinoate of Chemical Formula 3. The process for preparing allylic disulfone compound of Chemical Formula 1 employs cyclo-geranyl sulfone, which reacts with C5 haloallylic sulfide to give rise to the chain-extended C15 thio-sulfone compound. The thio-sulfone compound is selectively oxidized to give allylic disulfone of Chemical Formula 1. The C15 disulfone compound reacts with C5 halo-acid or C5 halo-ester under the condition using excess base, which induces coupling and subsequent desulfonation reactions to give retinoic acid of Chemical Formula 2 or alkyl retinoate of Chemical Formula 3.
• [EN] PRACTICAL SYNTHETIC METHOD OF RETINOID AND CAROTENOID COMPOUNDS<br/>[FR] METHODE DE SYNTHESE PRATIQUE DE COMPOSES DE RETINOIDES ET DE CAROTENOIDES
  申请人：KOO SANGHO

  公开号：WO2002092560A1

  公开（公告）日：2002-11-21

  The present invention relates to an effective and practical method for preparing retinol (Chemical Formula 2), retinal (Chemical Formula 3) and βcarotene (Chemical Formula 4) by using C-15 allylic disulfone compound (Chemical Formula 1) as an intermediate compound, that is prepared through a stable and economic process, for syntheses of retinoid and carotenoid compounds.According to the present invention, retinol (Chemical Formula 2), retinal (Chemical Formula 3) and β-carotene (Chemical Formula 4) are effectively prepared, via coupling reaction of carbanion that is obtained from deprotonation of the C-15 disulfone compound (Chemical Formula 1) by excess amount (2 equivalents or more) of base, with C-5 halo-acetate compound (A), C-5 halo-acetal compound (C) and C-10 dihaloallylic sulfide compound (F), respectively followed by dehydrosulfonation reaction.
• General and systematic synthetic entry to carotenoid natural products
  作者：Young Cheol Jeong、Minkoo Ji、Jun Sup Lee、Jae-Deuk Yang、Jingquan Jin、Woonphil Baik、Sangho Koo

  DOI：10.1016/j.tet.2004.09.002

  日期：2004.11