ethyl 2-(diphenylmethylsilyl)levulinate ethylene ketal | 107126-17-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 2-(diphenylmethylsilyl)levulinate ethylene ketal
• 英文别名: Ethyl 3-(2-methyl-1,3-dioxolan-2-yl)-2-[methyl(diphenyl)silyl]propanoate
• CAS: 107126-17-0
• 化学式: C₂₂H₂₈O₄Si
• 分子量: 384.547
• InChiKey: QCKMFBKJNZPDDB-UHFFFAOYSA-N

物化性质

• 熔点：
  54-55 °C
• 沸点：
  452.0±43.0 °C(Predicted)
• 密度：
  1.167 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  2.97
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-(diphenylmethylsilyl)levulinate ethylene ketal 在 四氯化钛 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 77.75h， 生成 3-(2-hydroxyethoxy)-3-methyl-5-(diphenylmethylsilyl)-2-(2-phenylethyl)cyclopentanone
  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
• 作为产物：
  描述：

  2-甲基-1,3-二氧戊环-2-丙酸乙酯 、 甲基二苯基氯硅烷 在 lithium diisopropyl amide 作用下， 以82%的产率得到ethyl 2-(diphenylmethylsilyl)levulinate ethylene ketal
  参考文献：
  名称：

  Lopez-Cepero, Ingrid Montes de; Santiago, Angel; Larson, Gerald L., Synthetic Communications, 1986, vol. 16, # 6, p. 705 - 712

  摘要：

  DOI：

文献信息

• MONTES, DE, LOPEZ-CEPERO, I.;SANTIAGO, A.;LARSON, G. L., SYNTH. COMMUN., 1986, 16, N 6, 705-711
  作者：MONTES, DE, LOPEZ-CEPERO, I.、SANTIAGO, A.、LARSON, G. L.

  DOI：——

  日期：——
• 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.
• Lopez-Cepero, Ingrid Montes de; Santiago, Angel; Larson, Gerald L., Synthetic Communications, 1986, vol. 16, # 6, p. 705 - 712
  作者：Lopez-Cepero, Ingrid Montes de、Santiago, Angel、Larson, Gerald L.

  DOI：——

  日期：——