Ethyl 2-(oxan-2-ylmethyl)-4-oxobutanoate | 871738-73-7

• 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-(oxan-2-ylmethyl)-4-oxobutanoate
• 英文别名: ethyl 2-(oxan-2-ylmethyl)-4-oxobutanoate
• CAS: 871738-73-7
• 化学式: C₁₂H₂₀O₄
• 分子量: 228.288
• InChiKey: JQCFDVSMCSUHSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Ethyl 2-(oxan-2-ylmethyl)-4-oxobutanoate 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以93%的产率得到(4S,6R)-1,7-Dioxa-spiro[5.5]undecane-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  Room Temperature Intramolecular Hydro-O-alkylation of Aldehydes:  sp³ C−H Functionalization via a Lewis Acid Catalyzed Tandem 1,5-Hydride Transfer/Cyclization

  摘要：

  The scope and limitations of intramolecular hydro-O-alkylation of aldehyde substrates leading to spiroketals and bicyclic ketals and aminals is reported. The direct transformation of tertiary and sterically hindered secondary sp(3) C-H bonds into C-O bonds under the action of a catalytic amount of a variety of Lewis acids is described. The mechanism of these transformations is proposed to involve a tandem hydride transfer/cyclization sequence.

  DOI：

  10.1021/ol0522283
• 作为产物：
  描述：

  烯丙基丙二酸二乙酯 在 四氧化锇 sodium periodate 、 水 、 sodium hydride 、 lithium chloride 作用下， 以 乙醚 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 2.33h， 生成 Ethyl 2-(oxan-2-ylmethyl)-4-oxobutanoate
  参考文献：
  名称：

  Room Temperature Intramolecular Hydro-O-alkylation of Aldehydes:  sp³ C−H Functionalization via a Lewis Acid Catalyzed Tandem 1,5-Hydride Transfer/Cyclization

  摘要：

  The scope and limitations of intramolecular hydro-O-alkylation of aldehyde substrates leading to spiroketals and bicyclic ketals and aminals is reported. The direct transformation of tertiary and sterically hindered secondary sp(3) C-H bonds into C-O bonds under the action of a catalytic amount of a variety of Lewis acids is described. The mechanism of these transformations is proposed to involve a tandem hydride transfer/cyclization sequence.

  DOI：

  10.1021/ol0522283

文献信息

• Room Temperature Intramolecular Hydro-O-alkylation of Aldehydes:  sp³ C−H Functionalization via a Lewis Acid Catalyzed Tandem 1,5-Hydride Transfer/Cyclization
  作者：Stefan J. Pastine、Dalibor Sames

  DOI：10.1021/ol0522283

  日期：2005.11.1

  The scope and limitations of intramolecular hydro-O-alkylation of aldehyde substrates leading to spiroketals and bicyclic ketals and aminals is reported. The direct transformation of tertiary and sterically hindered secondary sp(3) C-H bonds into C-O bonds under the action of a catalytic amount of a variety of Lewis acids is described. The mechanism of these transformations is proposed to involve a tandem hydride transfer/cyclization sequence.