(4Z)-8-methyl-4-prop-2-enylnona-4,8-dien-1-ol | 216150-95-7

• 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: (4Z)-8-methyl-4-prop-2-enylnona-4,8-dien-1-ol
• CAS: 216150-95-7
• 化学式: C₁₃H₂₂O
• 分子量: 194.317
• InChiKey: KNHNHUAFQXBTGN-UKTHLTGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.54
• 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：

  (4Z)-8-methyl-4-prop-2-enylnona-4,8-dien-1-ol 在 lithium aluminium tetrahydride 、 重铬酸吡啶 、 甲基磺酰氯 、 三乙胺 、 lithium bromide 作用下， 以 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 13.0h， 生成 (5Z,9E)-11-bromo-2,10-dimethyl-6-prop-2-enylundeca-1,5,9-triene
  参考文献：
  名称：

  Total Syntheses of (±)-Isosteviol and (±)-Beyer-15-ene-3β,19-diol by Manganese(III)-Based Oxidative Quadruple Free-Radical Cyclization

  摘要：

  Tetraene 1 was prepared in nine steps from the known propargylic alcohol 7 in 17% overall yield or as a 2:1 E/Z mixture in only five steps in 7% overall yield. Oxidative cyclization of 1 with 2 equiv of Mn(OAc)(3). 2H(2)O and 1 equiv of Cu(OAc)(2) in MeOH at 25 degrees C provided 35% of tetracycle 2. Further elaboration provided (+/-)-isosteviol (3) in six steps in 51% yield and (+/-)-beyer-15-ene-3 beta,19-diol in four steps in 17% yield.

  DOI：

  10.1021/jo981238x
• 作为产物：
  描述：

  (4E)-4-(bromomethyl)-8-methylnona-1,4,8-triene 在 copper(l) iodide 、 lithium aluminium tetrahydride 、 lithium diisopropyl amide 作用下， 以 乙醚 为溶剂， 反应 1.0h， 生成 (4Z)-8-methyl-4-prop-2-enylnona-4,8-dien-1-ol
  参考文献：
  名称：

  Total Syntheses of (±)-Isosteviol and (±)-Beyer-15-ene-3β,19-diol by Manganese(III)-Based Oxidative Quadruple Free-Radical Cyclization

  摘要：

  Tetraene 1 was prepared in nine steps from the known propargylic alcohol 7 in 17% overall yield or as a 2:1 E/Z mixture in only five steps in 7% overall yield. Oxidative cyclization of 1 with 2 equiv of Mn(OAc)(3). 2H(2)O and 1 equiv of Cu(OAc)(2) in MeOH at 25 degrees C provided 35% of tetracycle 2. Further elaboration provided (+/-)-isosteviol (3) in six steps in 51% yield and (+/-)-beyer-15-ene-3 beta,19-diol in four steps in 17% yield.

  DOI：

  10.1021/jo981238x

文献信息

• Total Syntheses of (±)-Isosteviol and (±)-Beyer-15-ene-3β,19-diol by Manganese(III)-Based Oxidative Quadruple Free-Radical Cyclization
  作者：Barry B. Snider、Jane Y. Kiselgof、Bruce M. Foxman

  DOI：10.1021/jo981238x

  日期：1998.10.1

  Tetraene 1 was prepared in nine steps from the known propargylic alcohol 7 in 17% overall yield or as a 2:1 E/Z mixture in only five steps in 7% overall yield. Oxidative cyclization of 1 with 2 equiv of Mn(OAc)(3). 2H(2)O and 1 equiv of Cu(OAc)(2) in MeOH at 25 degrees C provided 35% of tetracycle 2. Further elaboration provided (+/-)-isosteviol (3) in six steps in 51% yield and (+/-)-beyer-15-ene-3 beta,19-diol in four steps in 17% yield.