2-Allyl-2-(tetrahydro-pyran-2-ylmethyl)-malonic acid diethyl ester | 871739-02-5

• 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: 2-Allyl-2-(tetrahydro-pyran-2-ylmethyl)-malonic acid diethyl ester
• CAS: 871739-02-5
• 化学式: C₁₆H₂₆O₅
• 分子量: 298.379
• InChiKey: VGMSFGGELQOFGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.63
• 重原子数：
  21.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-Allyl-2-(tetrahydro-pyran-2-ylmethyl)-malonic acid diethyl ester 在 臭氧 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 生成 diethyl 2-(oxan-2-ylmethyl)-2-[(E)-4-oxopent-2-enyl]propanedioate
  参考文献：
  名称：

  Room Temperature Hydroalkylation of Electron-Deficient Olefins:  sp³ C−H Functionalization via a Lewis Acid-Catalyzed Intramolecular Redox Event

  摘要：

  A practical method for the intramolecular hydroalkylation of electron-deficient olefins has been developed. The direct transformation of benzylic, tertiary, and sterically hindered secondary sp3 C-H bonds into C-C 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/ja053337f
• 作为产物：
  描述：

  2-(bromomethyl)tetrahydro-2H-pyran 、 烯丙基丙二酸二乙酯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 0.33h， 以61%的产率得到2-Allyl-2-(tetrahydro-pyran-2-ylmethyl)-malonic acid diethyl ester
  参考文献：
  名称：

  Room Temperature Hydroalkylation of Electron-Deficient Olefins:  sp³ C−H Functionalization via a Lewis Acid-Catalyzed Intramolecular Redox Event

  摘要：

  A practical method for the intramolecular hydroalkylation of electron-deficient olefins has been developed. The direct transformation of benzylic, tertiary, and sterically hindered secondary sp3 C-H bonds into C-C 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/ja053337f

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.