[2-(2-methyl-1-cycloheptenyl)-2-oxoethyl]phosphinic acid dimethyl ester | 672295-25-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: [2-(2-methyl-1-cycloheptenyl)-2-oxoethyl]phosphinic acid dimethyl ester
• 英文别名: 2-Dimethoxyphosphoryl-1-(2-methylcyclohepten-1-yl)ethanone
• CAS: 672295-25-9
• 化学式: C₁₂H₂₁O₄P
• 分子量: 260.27
• InChiKey: UFWBGNSINWKAGK-UHFFFAOYSA-N

物化性质

• 沸点：
  366.7±35.0 °C(Predicted)
• 密度：
  1.109±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  [2-(2-methyl-1-cycloheptenyl)-2-oxoethyl]phosphinic acid dimethyl ester 在 三氟甲磺酸 、 N,N-二异丙基乙胺 、 lithium chloride 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 49.0h， 生成 3-isopropyl-3a-methyl-3,3a,4,5,6,7-hexahydro-2H-azulen-1-one
  参考文献：
  名称：

  An Expeditious Nazarov Cyclization Strategy toward the Hydroazulene Core of Guanacastepene A

  摘要：

  The hydroazulene core of guanacastepene A has been synthesized in five steps from commercially available starting materials using a classical Nazarov cyclization to install the stereochemistry in the cyclopentanone diastereoselectively. In the presence or absence of Lewis bases, a hydroazulenone or a spirocyclic ketone generated via a novel Wagner-Meerwein rearrangement is obtained with excellent selectivity and yield.

  DOI：

  10.1021/ol036433z
• 作为产物：
  描述：

  2-氧代-1-环庚烷甲酸甲酯 在 正丁基锂 、 sodium hydride 、 氯磷酸二甲酯 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 生成 [2-(2-methyl-1-cycloheptenyl)-2-oxoethyl]phosphinic acid dimethyl ester
  参考文献：
  名称：

  An Expeditious Nazarov Cyclization Strategy toward the Hydroazulene Core of Guanacastepene A

  摘要：

  The hydroazulene core of guanacastepene A has been synthesized in five steps from commercially available starting materials using a classical Nazarov cyclization to install the stereochemistry in the cyclopentanone diastereoselectively. In the presence or absence of Lewis bases, a hydroazulenone or a spirocyclic ketone generated via a novel Wagner-Meerwein rearrangement is obtained with excellent selectivity and yield.

  DOI：

  10.1021/ol036433z

文献信息

• An Expeditious Nazarov Cyclization Strategy toward the Hydroazulene Core of Guanacastepene A
  作者：Pauline Chiu、Shuoliang Li

  DOI：10.1021/ol036433z

  日期：2004.2.1

  The hydroazulene core of guanacastepene A has been synthesized in five steps from commercially available starting materials using a classical Nazarov cyclization to install the stereochemistry in the cyclopentanone diastereoselectively. In the presence or absence of Lewis bases, a hydroazulenone or a spirocyclic ketone generated via a novel Wagner-Meerwein rearrangement is obtained with excellent selectivity and yield.