(4E,8Z,12E)-hexadecatriene-1,16-diol | 221367-79-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (4E,8Z,12E)-hexadecatriene-1,16-diol
• 英文别名: (4E,8Z,12E)-hexadeca-4,8,12-triene-1,16-diol
• CAS: 221367-79-9
• 化学式: C₁₆H₂₈O₂
• 分子量: 252.397
• InChiKey: UKXPLDTVJYTDKF-RYMQXAEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4E,8Z,12E)-hexadecatriene-1,16-diol 在 palladium on activated charcoal 吡啶 、 盐酸 、 iodonium di(2,4,6-trimethylpyridine) perchlorate 、 硫酸 、 camphor-10-sulfonic acid 、 氢气 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 作用下， 以 四氢呋喃 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 (R)-1-[(2R,5R,2'S,5'R)-5'-((R)-1-Hydroxy-undecyl)-octahydro-[2,2']bifuranyl-5-yl]-butane-1,4-diol
  参考文献：
  名称：

  A novel desymmetrization reaction of an acetogenin precursor: A formal synthesis of trilobacin and asimicin

  摘要：

  A two-directional strategy which is based on the haloetherification reaction of a bis-5,6-O-isopropylidene alkene, is applied to the synthesis of a versatile relay compound for the bis-THF containing acetogenins. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)80016-6
• 作为产物：
  描述：

  (Z)-1,6,11-dodecatriene-3,10-diol 在 二异丁基氢化铝 、 丙酸 作用下， 以 正庚烷 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (4E,8Z,12E)-hexadecatriene-1,16-diol
  参考文献：
  名称：

  1,2-O-Isopropylidene-5-alkene templates for the synthesis of oligo-tetrahydrofurans

  摘要：

  The highly functionalized THF 4 was prepared in eight steps from 2,5-cyclooctadiene. The key step in this synthesis was a novel desymmetrization reaction involving the iodoetherification of the C2 symmetric bis-isopropylidene alkene 6 to THF 4. The versatility of 4 was demonstrated by its conversion to bis-THF 3, a known precursor for trilobacin, and to the tris-THF-lactone 5, a potential relay compound for cyclic polyether analogues. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00075-3

文献信息

• 1,2-O-Isopropylidene-5-alkene templates for the synthesis of oligo-tetrahydrofurans
  作者：Darrin Dabideen、Zheming Ruan、David R Mootoo

  DOI：10.1016/s0040-4020(02)00075-3

  日期：2002.3

  The highly functionalized THF 4 was prepared in eight steps from 2,5-cyclooctadiene. The key step in this synthesis was a novel desymmetrization reaction involving the iodoetherification of the C2 symmetric bis-isopropylidene alkene 6 to THF 4. The versatility of 4 was demonstrated by its conversion to bis-THF 3, a known precursor for trilobacin, and to the tris-THF-lactone 5, a potential relay compound for cyclic polyether analogues. (C) 2002 Elsevier Science Ltd. All rights reserved.
• A novel desymmetrization reaction of an acetogenin precursor: A formal synthesis of trilobacin and asimicin
  作者：Zheming Ruan、David R. Mootoo

  DOI：10.1016/s0040-4039(98)80016-6

  日期：1999.1

  A two-directional strategy which is based on the haloetherification reaction of a bis-5,6-O-isopropylidene alkene, is applied to the synthesis of a versatile relay compound for the bis-THF containing acetogenins. (C) 1998 Elsevier Science Ltd. All rights reserved.