4-(3,3-dimethylbutyl)-1,8-nonadien-5-one | 142762-92-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(3,3-dimethylbutyl)-1,8-nonadien-5-one
• 英文别名: 9,9-Dimethyl-6-prop-2-enyldec-1-en-5-one
• CAS: 142762-92-3
• 化学式: C₁₅H₂₆O
• 分子量: 222.371
• InChiKey: WVFGFVWNQGGCJM-UHFFFAOYSA-N

物化性质

• 沸点：
  296.2±9.0 °C(Predicted)
• 密度：
  0.842±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  16
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-戊烯酸乙酯 在 sodium ethanolate 、 potassium hydride 、 lithium iodide 作用下， 反应 31.0h， 生成 4-(3,3-dimethylbutyl)-1,8-nonadien-5-one
  参考文献：
  名称：

  Total synthesis of (.+-.)-velloziolone.

  摘要：

  The first total synthesis of the 9,10-seco-kaurene velloziolone (3) has been accomplished using an atom transfer tandem free-radical cyclization to prepare the 6-methylenebicyclo[3.2.1]octan-2-one moiety. The known diol 11 is converted to iodo acetate 10 in three steps. Alkylation of beta-keto ester 22 with 10 affords 33 that is converted to alpha-iodo ketone 7 in one pot by silylation, followed by palladium-catalyzed decarboxylation to give the tetra-substituted silyl enol ether regiospecifically and iodination of the enol ether. Atom transfer cyclization at 150-degrees-C, but not at 25 or 85-degrees-C, provides a mixture of bicyclic iodides. Elimination of HI and hydrolysis of the acetate furnishes velloziolone.

  DOI：

  10.1021/jo00044a024

文献信息

• Total synthesis of (.+-.)-velloziolone.
  作者：Barry B. Snider、Brad O. Buckman

  DOI：10.1021/jo00044a024

  日期：1992.8

  The first total synthesis of the 9,10-seco-kaurene velloziolone (3) has been accomplished using an atom transfer tandem free-radical cyclization to prepare the 6-methylenebicyclo[3.2.1]octan-2-one moiety. The known diol 11 is converted to iodo acetate 10 in three steps. Alkylation of beta-keto ester 22 with 10 affords 33 that is converted to alpha-iodo ketone 7 in one pot by silylation, followed by palladium-catalyzed decarboxylation to give the tetra-substituted silyl enol ether regiospecifically and iodination of the enol ether. Atom transfer cyclization at 150-degrees-C, but not at 25 or 85-degrees-C, provides a mixture of bicyclic iodides. Elimination of HI and hydrolysis of the acetate furnishes velloziolone.