7,7-(ethylenedioxy)-4-propyl-4-octanol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7,7-(ethylenedioxy)-4-propyl-4-octanol
• 英文别名: 4-[2-(2-Methyl-1,3-dioxolan-2-yl)ethyl]heptan-4-ol
• 化学式: C₁₃H₂₆O₃
• 分子量: 230.348
• InChiKey: CWUCAGXILSVBSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  丙基溴化镁 、 ethyl 2-(diphenylmethylsilyl)levulinate ethylene ketal 以 四氢呋喃 为溶剂， 反应 72.0h， 以87%的产率得到7,7-(ethylenedioxy)-5-(diphenylmethylsilyl)-4-octanone
  参考文献：
  名称：

  Highly substituted .alpha.-silylated cyclopentanones from ethyl levulinate: an entry to a methylenomycin B analog

  摘要：

  The transformation of alpha-diphenylmethylsilylated ethyl levulinate acetal, 1, to a series of alpha-silylated cyclopentanones has been studied. The approach was based on a three-step process in which 1 was initially transformed into alpha-(diphenylmethylsilyl)-gamma-(ethylenedioxy) ketones by its reaction with Grignard reagents. A novel highly substituted 2,3-dihydrofuran was also obtained as a secondary product. Deprotonation-trimethylsilylation of these ketones under kinetic conditions produced 3-silylated-2-silyl enol ethers in a regio- and stereoselective manner. The Z isomer was shown to predominate. These enol ethers were stereoselectively transformed into alpha-silylated cyclopentanones by a TiCl4-promoted intramolecular Mukaiyama reaction. The geometry of the silyl enol ethers determined the stereochemistry of the cyclic ketone products, and the integrity of the diphenylmethylsilyl group was maintained. A methylenomycin B analog was prepared in one pot from one of the polyfunctional ketones by means of a beta-alkoxy elimination followed by a Peterson-type alpha-methylenation with formaldehyde. This analog, 3-methyl-5-methylene-2-(2-phenylethyl)-2-cyclopenten-1-one, 12, showed in vitro cytotoxicity against CHO-K1 cells.

  DOI：

  10.1021/jo00062a012

文献信息

• Highly substituted .alpha.-silylated cyclopentanones from ethyl levulinate: an entry to a methylenomycin B analog
  作者：Osvaldo Villanueva、Jose A. Prieto

  DOI：10.1021/jo00062a012

  日期：1993.5

  The transformation of alpha-diphenylmethylsilylated ethyl levulinate acetal, 1, to a series of alpha-silylated cyclopentanones has been studied. The approach was based on a three-step process in which 1 was initially transformed into alpha-(diphenylmethylsilyl)-gamma-(ethylenedioxy) ketones by its reaction with Grignard reagents. A novel highly substituted 2,3-dihydrofuran was also obtained as a secondary product. Deprotonation-trimethylsilylation of these ketones under kinetic conditions produced 3-silylated-2-silyl enol ethers in a regio- and stereoselective manner. The Z isomer was shown to predominate. These enol ethers were stereoselectively transformed into alpha-silylated cyclopentanones by a TiCl4-promoted intramolecular Mukaiyama reaction. The geometry of the silyl enol ethers determined the stereochemistry of the cyclic ketone products, and the integrity of the diphenylmethylsilyl group was maintained. A methylenomycin B analog was prepared in one pot from one of the polyfunctional ketones by means of a beta-alkoxy elimination followed by a Peterson-type alpha-methylenation with formaldehyde. This analog, 3-methyl-5-methylene-2-(2-phenylethyl)-2-cyclopenten-1-one, 12, showed in vitro cytotoxicity against CHO-K1 cells.