4,5,6,6a-Tetrahydro-3,5,5-trimethyl-2(1H)-pentalenone | 68691-09-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯基酸
• 英文名称: 4,5,6,6a-Tetrahydro-3,5,5-trimethyl-2(1H)-pentalenone
• 英文别名: 2,7,7-Trimethylbicyclo<3.3.0>oct-1-en-3-on；3,5,5-Trimethyl-1,4,6,6a-tetrahydropentalen-2-one
• CAS: 68691-09-8
• 化学式: C₁₁H₁₆O
• 分子量: 164.247
• InChiKey: CUFTXAMAZDIRRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  4,5,6,6a-Tetrahydro-3,5,5-trimethyl-2(1H)-pentalenone 在 sodium hydroxide 、 二甲基硫 、 双氧水 、 potassium hydride 、 对甲苯磺酸 、 臭氧 、 一水合肼 作用下， 以 四氢呋喃 、 甲醇 、 苯 为溶剂， 反应 167.0h， 生成 cis-1,2,3,3a,7,7a-Hexahydro-2,2-dimethyl-3a-(phenylmethoxy)-4H-inden-4-one
  参考文献：
  名称：

  1,3-Elimination reactions of (3,4-epoxybutyl)stannanes. Approach to the synthesis of hirsutene

  摘要：

  An advanced tricyclic precursor of hirsutene (3) was prepared by a 1,3-elimination reaction of spirocyclic epoxy stannane 7b. Compound 7b was synthesized efficiently from hydroxycyclohexenone 8b by conjugate addition of [(CH3)3Sn]2CuLi, Wittig methylenation, and VO(acac)2-catalyzed epoxidation. Intermediate 8b was prepared in five steps from the known enone 9 in 18% overall yield. An improved synthesis makes compound 9 available in four efficient steps from keto ester 12.

  DOI：

  10.1021/jo00006a020
• 作为产物：
  描述：

  Methyl 4,4-Dimethyl-1-(2-methylenebutyl)-2-oxocyclopentanecarboxylate 在 sodium hydride 、 臭氧 、 溶剂黄146 、 lithium iodide 、 锌 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 39.75h， 生成 4,5,6,6a-Tetrahydro-3,5,5-trimethyl-2(1H)-pentalenone
  参考文献：
  名称：

  1,3-Elimination reactions of (3,4-epoxybutyl)stannanes. Approach to the synthesis of hirsutene

  摘要：

  An advanced tricyclic precursor of hirsutene (3) was prepared by a 1,3-elimination reaction of spirocyclic epoxy stannane 7b. Compound 7b was synthesized efficiently from hydroxycyclohexenone 8b by conjugate addition of [(CH3)3Sn]2CuLi, Wittig methylenation, and VO(acac)2-catalyzed epoxidation. Intermediate 8b was prepared in five steps from the known enone 9 in 18% overall yield. An improved synthesis makes compound 9 available in four efficient steps from keto ester 12.

  DOI：

  10.1021/jo00006a020

文献信息

• Fungal extractives. 12. Construction of the vellerane skeleton with total syntheses of racemic velleral, vellerolactone, and pyrovellerolactone. Revised structures
  作者：Jan Froborg、Goran Magnusson

  DOI：10.1021/ja00489a030

  日期：1978.10
• PLAMONDON, LOUIS;WUEST, JAMES D., J. ORG. CHEM., 56,(1991) N, C. 2076-2081
  作者：PLAMONDON, LOUIS、WUEST, JAMES D.

  DOI：——

  日期：——