(E)-(2-(benzo[d][1,3]dioxol-5-yl)vinyl)diphenylphosphine oxide | 65164-86-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: (E)-(2-(benzo[d][1,3]dioxol-5-yl)vinyl)diphenylphosphine oxide
• 英文别名: 5-[(E)-2-diphenylphosphorylethenyl]-1,3-benzodioxole
• CAS: 65164-86-5
• 化学式: C₂₁H₁₇O₃P
• 分子量: 348.338
• InChiKey: HLIHAWVZNNIWMJ-BUHFOSPRSA-N

物化性质

• 沸点：
  560.8±50.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  Diphenylphosphine oxide 、 3,4-methylenedioxy-trans-cinnamic acid 在 dipotassium hydrogenphosphate 、 过氧化苯甲酸叔丁酯 、 potassium iodide 作用下， 以 二甲基亚砜 为溶剂， 反应 12.0h， 以71%的产率得到(E)-(2-(benzo[d][1,3]dioxol-5-yl)vinyl)diphenylphosphine oxide
  参考文献：
  名称：

  Transition-Metal-Free C–P Bond Formation via Decarboxylative Phosphorylation of Cinnamic Acids with P(O)H Compounds

  摘要：

  A novel, transition-metal-free phosphorylation of cinnamic acids with P(O)H compounds has been developed via radical-promoted decarboxylation under mild conditions. This method provides simple, efficient, and versatile access to valuable (E)-alkenylphosphine oxides in satisfactory yields with a wide variety of substrates.

  DOI：

  10.1021/acs.joc.8b00187

文献信息

• Copper-Catalyzed C-P Coupling through Decarboxylation
  作者：Jie Hu、Ning Zhao、Bin Yang、Ge Wang、Li-Na Guo、Yong-Min Liang、Shang-Dong Yang

  DOI：10.1002/chem.201003561

  日期：2011.5.9

  developed by copper‐catalyzed decarboxylative coupling of alkenyl, alkynyl carboxylic acids, and N‐benzylproline, respectively, with R2P(O)H (see scheme). All classes of products are important precursors for preparation of biologically active molecules and various phosphorus ligands. This finding represents the first example of copper‐catalyzed decarboxylative coupling to construct CP bonds.

  膦酸：通过铜催化的烯基，炔基羧酸和N-苄基脯氨酸分别与R 2 P（O）H（参见方案）。所有种类的产品都是制备生物活性分子和各种磷配体的重要前体。这一发现表示铜催化脱羧耦合构造C的第一示例 P键。
• Transition-Metal-Free C–P Bond Formation via Decarboxylative Phosphorylation of Cinnamic Acids with P(O)H Compounds
  作者：Lixin Liu、Dan Zhou、Jianyu Dong、Yongbo Zhou、Shuang-Feng Yin、Li-Biao Han

  DOI：10.1021/acs.joc.8b00187

  日期：2018.4.6

  A novel, transition-metal-free phosphorylation of cinnamic acids with P(O)H compounds has been developed via radical-promoted decarboxylation under mild conditions. This method provides simple, efficient, and versatile access to valuable (E)-alkenylphosphine oxides in satisfactory yields with a wide variety of substrates.