5-isopropyl-7-methylenespiro[4.5]decan-2-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-isopropyl-7-methylenespiro[4.5]decan-2-one
• 英文别名: (5R,7R)-4-methylidene-7-propan-2-ylspiro[4.5]decan-10-one
• 化学式: C₁₄H₂₂O
• 分子量: 206.328
• InChiKey: FIGPKZTYJKSNPU-TZMCWYRMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-isopropyl-7-methylenespiro[4.5]decan-2-one 、 亚甲基三苯基膦烷 以 四氢呋喃 为溶剂， 生成 (5R,7S)-4,10-dimethylidene-7-propan-2-ylspiro[4.5]decane
  参考文献：
  名称：

  A stereoselective total synthesis of (±)-erythrodiene

  摘要：

  Erythrodiene, a unique spirobicyclic sesquiterpene hydrocarbon from the Caribbean gorgonian cord Erythropodium caribaeorum, has been synthesized from 4-isopropylcyclohexanol in 8-steps and approximately 16% overall yield. The synthesis features a stereoselective intramolecular carbomercuration reaction as the key step.

  DOI：

  10.1016/s0040-4039(00)61502-2
• 作为产物：
  描述：

  5-isopropyl-2-oxocyclohexanecarboxylic acid methyl ester 在 盐酸 、 水 、 potassium hydride 、 六甲基二硅氮烷 、 sodium iodide 、 mercury dichloride 、 lithium iodide 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 5-isopropyl-7-methylenespiro[4.5]decan-2-one
  参考文献：
  名称：

  A stereoselective total synthesis of (±)-erythrodiene

  摘要：

  Erythrodiene, a unique spirobicyclic sesquiterpene hydrocarbon from the Caribbean gorgonian cord Erythropodium caribaeorum, has been synthesized from 4-isopropylcyclohexanol in 8-steps and approximately 16% overall yield. The synthesis features a stereoselective intramolecular carbomercuration reaction as the key step.

  DOI：

  10.1016/s0040-4039(00)61502-2

文献信息

• A Silver-Catalyzed Spirocyclization of Alkynyl Silyl Enol Ethers
  作者：Christian Schäfer、Michel Miesch、Laurence Miesch

  DOI：10.1002/chem.201200116

  日期：2012.6.25

  Ring out the old: The cycloisomerization of alkynyl silyl enol ethers proceeds at ambient temperature under the mild conditions of silver catalysis (see scheme). Mono‐ or bicyclic spiro compounds can be obtained by 5‐exo‐dig reactions. Trapping the vinyl silver species with an iodide source, such as N‐iodosuccinimide (NIS), afforded the alkenyl iodide derivatives.

  摆脱陈旧：炔基甲硅烷基烯醇醚的环异构化反应在环境温度下，在银催化的温和条件下进行（参见方案）。单环或双环螺化合物可通过5-外切反应获得。用碘化物源（如N-碘琥珀酰亚胺（NIS））捕获乙烯基银物质，得到烯基碘化物衍生物。
• A stereoselective total synthesis of (±)-erythrodiene
  作者：He Huang、Craig J. Forsyth

  DOI：10.1016/s0040-4039(00)61502-2

  日期：1993.12

  Erythrodiene, a unique spirobicyclic sesquiterpene hydrocarbon from the Caribbean gorgonian cord Erythropodium caribaeorum, has been synthesized from 4-isopropylcyclohexanol in 8-steps and approximately 16% overall yield. The synthesis features a stereoselective intramolecular carbomercuration reaction as the key step.