(1S,5R,9R)-1-Iodomethyl-9-isopropyl-6-methylene-spiro[4.5]decane | 339157-73-2

• 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: (1S,5R,9R)-1-Iodomethyl-9-isopropyl-6-methylene-spiro[4.5]decane
• CAS: 339157-73-2
• 化学式: C₁₅H₂₅I
• 分子量: 332.268
• InChiKey: HNBDBXCWQRTLNR-KFWWJZLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.22
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  (1S,5R,9R)-1-Iodomethyl-9-isopropyl-6-methylene-spiro[4.5]decane 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 以98%的产率得到(+/-)-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：

  Acetic acid (R)-4-isopropyl-2-pent-4-enyl-cyclohex-1-enylmethyl ester 在 四(三苯基膦)钯 、 diethylzinc 作用下， 以 乙醚 为溶剂， 生成 (1S,5R,9R)-1-Iodomethyl-9-isopropyl-6-methylene-spiro[4.5]decane
  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

文献信息

• Synthesis of (−)-Erythrodiene and (+)-7-Epispirojatamolvia Intramolecular Pd-Catalyzed Allylzincation
  作者：Wolfgang Oppolzer、Felix Flachsmann

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

  日期：2001.2.28

  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.