6-(4'-Methylphenyl)-2,6-heptadien-1-ol | 162250-36-4

• 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: 6-(4'-Methylphenyl)-2,6-heptadien-1-ol
• 英文别名: (2E)-6-(4-methylphenyl)hepta-2,6-dien-1-ol
• CAS: 162250-36-4
• 化学式: C₁₄H₁₈O
• 分子量: 202.296
• InChiKey: ZTMSDVRJMBVJNE-HWKANZROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-(4'-Methylphenyl)-2,6-heptadien-1-ol 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 4 A molecular sieve 、 D-(-)-酒石酸二异丙酯 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以91%的产率得到(2R,3R)-2,3-Epoxy-6-(4'-methylphenyl)-6-hepten-1-ol
  参考文献：
  名称：

  Enantioselective Total Syntheses and Stereochemical Studies of All Four Stereoisomers of Yingzhaosu C

  摘要：

  The enantioselective total syntheses and the stereochemistry of all four stereoisomers of yingzhaosu C, an antimalarial peroxy-containing sesquiterpene isolated from yingzhao [Artabotrys uncinatus (L.) Merr.], are described. The key to the syntheses was the combination of Sharpless asymmetric epoxidation and the intramolecular nucleophilic epoxy-opening with a benzylic peroxy group to construct the 1,2-dioxane skeleton. The configurations of the 1,2-dioxanes in four stereoisomers were assigned by spectroscopy and chemical transformation.

  DOI：

  10.1021/jo00115a019
• 作为产物：
  描述：

  6-(4'-Methylphenyl)-2,6-heptadienoic acid ethyl ester 在 二异丁基氢化铝 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 1.0h， 以98%的产率得到6-(4'-Methylphenyl)-2,6-heptadien-1-ol
  参考文献：
  名称：

  Enantioselective Total Syntheses and Stereochemical Studies of All Four Stereoisomers of Yingzhaosu C

  摘要：

  The enantioselective total syntheses and the stereochemistry of all four stereoisomers of yingzhaosu C, an antimalarial peroxy-containing sesquiterpene isolated from yingzhao [Artabotrys uncinatus (L.) Merr.], are described. The key to the syntheses was the combination of Sharpless asymmetric epoxidation and the intramolecular nucleophilic epoxy-opening with a benzylic peroxy group to construct the 1,2-dioxane skeleton. The configurations of the 1,2-dioxanes in four stereoisomers were assigned by spectroscopy and chemical transformation.

  DOI：

  10.1021/jo00115a019

文献信息

• Enantioselective total synthesis of all four stereoisomers of Yingzhaosu C
  作者：Xing-Xiang Xu、Han-Qing Dong

  DOI：10.1016/s0040-4039(00)78561-3

  日期：1994.12

  An enantioselective total synthesis of all four stereoisomers of Yingzhaosu C, an antimalarial peroxy-containing sesquiterpene isolated from Yingzhao [Artabotrys uncinatus(L.) Merr.], is described.

  描述了映照素C的所有四个立体异构体的对映选择性全合成，映照素C是从映照[ Artabotrys uncinatus（L.）Merr。]分离的一种抗疟疾的含过氧化物的倍半萜烯。