tert-butyl (2-(diethoxyphosphoryl)-1-phenylallyl) carbonate | 1316312-90-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-butyl (2-(diethoxyphosphoryl)-1-phenylallyl) carbonate
• CAS: 1316312-90-9
• 化学式: C₁₈H₂₇O₆P
• 分子量: 370.383
• InChiKey: UWAAKRLSNMNYMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.46
• 重原子数：
  25.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (2-(diethoxyphosphoryl)-1-phenylallyl) carbonate 在 三乙烯二胺 、 水 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.5h， 以76%的产率得到diethyl 1-[hydroxy(phenyl)methyl]vinylphosphonate
  参考文献：
  名称：

  Lewis Base Catalyzed Enantioselective Allylic Hydroxylation of Morita–Baylis–Hillman Carbonates with Water

  摘要：

  A Lewis base catalyzed allylic hydroxylation of Morita-Baylis-Hillman (MBH) carbonates has been developed. Various chiral MBH alcohols can be synthesized in high yields (up to 99%) and excellent enantioselectivities (up to 94% ee). This is the first report using water as a nucleophile in asymmetric organocatalysis. The nucleophilic role of water has been verified using O-18-labeling experiments.

  DOI：

  10.1021/jo201096e

文献信息

• Highly regio- and diastereoselective construction of spirocyclopenteneoxindole phosphonates through a phosphine-catalyzed [3 + 2] annulation reaction
  作者：Chengbin Yu、Weiping Zheng、Junchen Zhan、Yuchao Sun、Zhiwei Miao

  DOI：10.1039/c4ra12997k

  日期：——

  A phosphine-catalyzed [3 + 2] annulation of MBH phosphonates with isatylidene malononitriles is developed. The described method, which is different from most traditional phosphorus ylide intermediate reaction modes of MBH carbonates with isatylidene malononitriles, represents a novel approach to highly regioselective and diastereoselective synthesis of spirocyclopenteneoxindole phosphonates.

  开发了膦催化的[3 + 2]环烷磺酸膦与异亚丙基丙二腈的环化反应。所描述的方法不同于大多数传统的MBH碳酸酯与异亚丙基丙二腈的磷叶立德中间体反应模式，代表了一种高区域选择性和非对映选择性合成螺环戊烯氧吲哚膦酸酯的新方法。