all-(E)-2,6,11,15-tetramethyl-hexadeca-2,4,6,8,10,12,14-heptaene | 74274-35-4

• 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: all-(E)-2,6,11,15-tetramethyl-hexadeca-2,4,6,8,10,12,14-heptaene
• 英文别名: (all-E)-2,6,11,15-Tetramethyl-2,4,6,8,10,12,14-hexadecaheptaen；(all-E)-2,6,11,15-tetramethyl-hexadeca-2,4,6,8,10,12,14-heptaene；8,8'-diapo-carotene；2,6,11,15-Tetramethyl-hexadecahaptaen-(2,4,6,8,10,12,14)；(all-E)-tetradehydro-bigeranylidene；(4E,6E,8E,10E,12E)-2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-heptaene
• CAS: 74274-35-4
• 化学式: C₂₀H₂₈
• 分子量: 268.442
• InChiKey: RCGRLMLIURQCQY-NPTOWFBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  2,2,4,4-tetrakis(ethoxycarbonyl)-(E)-4-octene 在 氢氧化钾 、 lithium aluminium tetrahydride 、 正丁基锂 、 草酰氯 、 硫酸 、 potassium methanolate 、 phosphorus pentoxide 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 环己烷 、 水 为溶剂， 反应 171.83h， 生成 all-(E)-2,6,11,15-tetramethyl-hexadeca-2,4,6,8,10,12,14-heptaene
  参考文献：
  名称：

  Sulfone Coupling and Double-Elimination Strategy for Carotenoid Synthesis

  摘要：

  A highly efficient synthetic method of carotenoid compounds has been developed on the basis of the sulfone coupling and double-elimination strategy. This method highlighted the sulfone-mediated coupling with the novel C-10 dialdehyde, 2,7-dimethyl-4-octenedial, which was easily prepared and efficiently utilized in the synthesis of the conjugated polyene chains.

  DOI：

  10.1021/jo0516335

文献信息

• Synthese von Diterpenen als mögliche biogenetische Vorläufer des C₂₀-Carotinoides Crocetin
  作者：Heidi Schurtenberger、Ulrich Vögeli、Hanspeter Pfander

  DOI：10.1002/hlca.19830660746

  日期：1983.11.2

  Synthesis of Diterpenes as Possible Biogenetic Precursors of the C20-Carotenoid Crocetin

  二萜类化合物的合成可能是C 20-类胡萝卜素藏花色素的生物遗传前体。
• 580. Studies in nuclear magnetic resonance. Part I. Methyl groups of carotenoids and related compounds
  作者：M. S. Barber、J. B. Davis、L. M. Jackman、B. C. L. Weedon

  DOI：10.1039/jr9600002870

  日期：——
• Efficient syntheses of C20-carotene and crocetin (descrocetin) esters promoted by an acidic ionic liquid
  作者：Galina V. Kryshtal、Galina M. Zhdankina、Nikolai V. Ignat’ev、Michael Schulte、Sergei G. Zlotin

  DOI：10.1016/j.tetlet.2012.07.015

  日期：2012.9

  Efficient syntheses of C-20-carotene and crocetin or descrocetin esters from fumaraldehyde bis-dimethylacetal are described. The key steps of these syntheses are the reactions of fumaraldehyde and (2E,4E,6E)-octa-2,4,6-trienedial bis-dimethylacetals with alkyl vinyl or alkyl propenyl ethers promoted by the acidic ionic liquid, [emim][HSO4].(C) 2012 Elsevier Ltd. All rights reserved.
• Sulfone Coupling and Double-Elimination Strategy for Carotenoid Synthesis
  作者：Samar Kumar Guha、Sangho Koo

  DOI：10.1021/jo0516335

  日期：2005.11.1

  A highly efficient synthetic method of carotenoid compounds has been developed on the basis of the sulfone coupling and double-elimination strategy. This method highlighted the sulfone-mediated coupling with the novel C-10 dialdehyde, 2,7-dimethyl-4-octenedial, which was easily prepared and efficiently utilized in the synthesis of the conjugated polyene chains.