(1R,5R)-5-isopropyl-2-methylidene-1-(pent-4-enyl)cyclohexanol | 339157-71-0

• 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: (1R,5R)-5-isopropyl-2-methylidene-1-(pent-4-enyl)cyclohexanol
• CAS: 339157-71-0
• 化学式: C₁₅H₂₆O
• 分子量: 222.371
• InChiKey: NTBHGNNVDKJOPR-HUUCEWRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.09
• 重原子数：
  16.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (1R,5R)-5-isopropyl-2-methylidene-1-(pent-4-enyl)cyclohexanol 在 四(三苯基膦)钯 、 potassium tert-butylate 、 diethylzinc 、 苯基锂 作用下， 以 乙醚 、 环己烷 、 溶剂黄146 、 二甲基亚砜 为溶剂， 反应 21.5h， 生成 (+/-)-erythrodiene
  参考文献：
  名称：

  Synthesis of (−)-Erythrodiene and (+)-7-Epispirojatamolvia Intramolecular Pd-Catalyzed Allylzincation

  摘要：

  Two spirobicyclic sesquiterpenoids, (-)-erythrodiene (1) and (+)-7-epispirojatamol (30),were synthesized in enantiomerically pure form via an intramolecular allylzincation process. The allylzinc species were formed in the presence of Et,Zn via transmetallation of a catalytically generated allylpalladium intermediate. Several Pd catalysts were tested for this transformation, and [Pd(OAc)(2)/Bu3P(1 equiv.) was found to be, by far, the most effective. Whereas the preparation of 1 involved allylzincation of a tethered terminal olefin. 30 was formed via a novel intramolecular allylzincation of a methyl ketone. Both reactions showed the same stereochemical preference. yielding the spirobicyclic products in 95:5 and 4:1 diastereoisomer ratios, respectively.

  DOI：

  10.1002/1522-2675(20010228)84:2<416::aid-hlca416>3.0.co;2-k
• 作为产物：
  描述：

  (+)-对-薄荷-1-烯 在 cerium(III) chloride 、 戴斯-马丁氧化剂 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 (1R,5R)-5-isopropyl-2-methylidene-1-(pent-4-enyl)cyclohexanol
  参考文献：
  名称：

  Synthesis of (−)-Erythrodiene and (+)-7-Epispirojatamolvia Intramolecular Pd-Catalyzed Allylzincation

  摘要：

  Two spirobicyclic sesquiterpenoids, (-)-erythrodiene (1) and (+)-7-epispirojatamol (30),were synthesized in enantiomerically pure form via an intramolecular allylzincation process. The allylzinc species were formed in the presence of Et,Zn via transmetallation of a catalytically generated allylpalladium intermediate. Several Pd catalysts were tested for this transformation, and [Pd(OAc)(2)/Bu3P(1 equiv.) was found to be, by far, the most effective. Whereas the preparation of 1 involved allylzincation of a tethered terminal olefin. 30 was formed via a novel intramolecular allylzincation of a methyl ketone. Both reactions showed the same stereochemical preference. yielding the spirobicyclic products in 95:5 and 4:1 diastereoisomer ratios, respectively.

  DOI：

  10.1002/1522-2675(20010228)84:2<416::aid-hlca416>3.0.co;2-k