ethyl (2E,4E,6E,8E,10E,12E)-3,7,11-trimethyl-13-(2,6,6-trimethyl-3-oxocyclohexen-1-yl)trideca-2,4,6,8,10,12-hexaenoate | 1332483-29-0

• 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: ethyl (2E,4E,6E,8E,10E,12E)-3,7,11-trimethyl-13-(2,6,6-trimethyl-3-oxocyclohexen-1-yl)trideca-2,4,6,8,10,12-hexaenoate
• CAS: 1332483-29-0
• 化学式: C₂₇H₃₆O₃
• 分子量: 408.581
• InChiKey: FNWDXGHYYWDUIL-LPDRRSDVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  斑蝥黄 、 ethyl (2E,4E/Z)-3-methylhexa-2,4-dienoate 在 Hoveyda-Grubbs catalyst second generation 作用下， 以 甲苯 为溶剂， 反应 96.0h， 生成 ethyl (11Z)-4-oxoretinoate 、 ethyl 4-oxoretinoate 、 、 ethyl (2E,4E,6E,8E,10E,12E)-3,7,11-trimethyl-13-(2,6,6-trimethyl-3-oxocyclohexen-1-yl)trideca-2,4,6,8,10,12-hexaenoate
  参考文献：
  名称：

  Cross metathesis approach to retinoids and other β-apocarotenoids

  摘要：

  Cross metathesis (CM) reactions between polyenes, such as beta-carotene, canthaxanthin or retinyl acetate, and various alkenes or dienes in the presence of second generation Hoveyda-Grubbs (H II) or Grubbs (G II) catalysts were investigated. Depending on the cross partner different apocarotenoids were obtained. Cross metathesis reactions of retinyl acetate proved to be fully regioselective. Carotenoid CM reactions afforded mixtures of two products due to competing cleavage of the C11-C12 and C15-C15' double bonds. However, regioselectivity can be controlled by choice of appropriate reaction conditions. The reactions of polyenes with dienes worked better in respect of yields and diastereoselectivities than those with monounsaturated cross partners. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.06.086

文献信息

• Cross metathesis approach to retinoids and other β-apocarotenoids
  作者：Agnieszka Wojtkielewicz、Jadwiga Maj、Agnieszka Dzieszkowska、Jacek Witold Morzycki

  DOI：10.1016/j.tet.2011.06.086

  日期：2011.9

  Cross metathesis (CM) reactions between polyenes, such as beta-carotene, canthaxanthin or retinyl acetate, and various alkenes or dienes in the presence of second generation Hoveyda-Grubbs (H II) or Grubbs (G II) catalysts were investigated. Depending on the cross partner different apocarotenoids were obtained. Cross metathesis reactions of retinyl acetate proved to be fully regioselective. Carotenoid CM reactions afforded mixtures of two products due to competing cleavage of the C11-C12 and C15-C15' double bonds. However, regioselectivity can be controlled by choice of appropriate reaction conditions. The reactions of polyenes with dienes worked better in respect of yields and diastereoselectivities than those with monounsaturated cross partners. (C) 2011 Elsevier Ltd. All rights reserved.