[(4E)-hepta-4,6-dienyl](phenyl)phosphinic acid | 461003-68-9

• 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: [(4E)-hepta-4,6-dienyl](phenyl)phosphinic acid
• 英文别名: [(4E)-hepta-4,6-dienyl]-phenylphosphinic acid
• CAS: 461003-68-9
• 化学式: C₁₃H₁₇O₂P
• 分子量: 236.251
• InChiKey: MVZJIYAQQOZGRR-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [(4E)-hepta-4,6-dienyl](phenyl)phosphinic acid 在 三甲基硅烷基二乙胺 、 草酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 4.75h， 生成 [(4E)-hepta-4,6-dienyl](phenyl)phosphinic chloride
  参考文献：
  名称：

  Diastereoselective and Intramolecular Cycloadditions of Asymmetric P-Nitroso Phosphine Oxides

  摘要：

  Benzyl phenyl P-nitroso phosphine oxide (5) reacts as an N-O heterodienophile with 1,3-cyclopentadiene to give the diastereomeric cycloadducts 6a,b in a ratio of 1.5:1 (6a:6b). The same reaction in the presence of tin tetrachloride produces 6a,b in a ratio of 2.9:1 (6a:6b). Cycloaddition of the structurally modified P-nitroso phosphine oxide (18) with 1,3-cyclopentadiene forms the diastereomeric cycloadducts 16a,b in a ratio of 3.1:1 (16a:16b). These results suggest the reactions of these P-nitroso phosphine oxides and 1,3-cyclopentadiene occur through a transition state where the heterodienophile adopts an s-cis conformation and approaches the diene in an exo fashion syn to the phenyl group. This model resembles those proposed for the cycloadditions of the structurally similar asymmetric vinyl phosphine oxides. Reaction of 18 with 1,3-cyclopentadiene in the presence of a Lewis acid produces cycloadducts 16ab in a ratio of 7:1 (16a:16b), which approaches synthetic utility. Similar experiments show that 1,3-cyclohexadiene likely reacts with P-nitroso phosphine oxides through a different transition state, limiting current predictions regarding the diastereoselectivity of these reactions. The intramolecular cycloaddition of an asymmetric P-nitroso phosphine oxide (19) for the first time produces a unique phosphorus-containing heterocyclic compound (20).

  DOI：

  10.1021/jo0202839
• 作为产物：
  描述：

  (4E)-hepta-4,6-dien-1-ol 在 三乙烯二胺 、 sodium hydroxide 、 lithium bromide 作用下， 以 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 119.5h， 生成 [(4E)-hepta-4,6-dienyl](phenyl)phosphinic acid
  参考文献：
  名称：

  Diastereoselective and Intramolecular Cycloadditions of Asymmetric P-Nitroso Phosphine Oxides

  摘要：

  Benzyl phenyl P-nitroso phosphine oxide (5) reacts as an N-O heterodienophile with 1,3-cyclopentadiene to give the diastereomeric cycloadducts 6a,b in a ratio of 1.5:1 (6a:6b). The same reaction in the presence of tin tetrachloride produces 6a,b in a ratio of 2.9:1 (6a:6b). Cycloaddition of the structurally modified P-nitroso phosphine oxide (18) with 1,3-cyclopentadiene forms the diastereomeric cycloadducts 16a,b in a ratio of 3.1:1 (16a:16b). These results suggest the reactions of these P-nitroso phosphine oxides and 1,3-cyclopentadiene occur through a transition state where the heterodienophile adopts an s-cis conformation and approaches the diene in an exo fashion syn to the phenyl group. This model resembles those proposed for the cycloadditions of the structurally similar asymmetric vinyl phosphine oxides. Reaction of 18 with 1,3-cyclopentadiene in the presence of a Lewis acid produces cycloadducts 16ab in a ratio of 7:1 (16a:16b), which approaches synthetic utility. Similar experiments show that 1,3-cyclohexadiene likely reacts with P-nitroso phosphine oxides through a different transition state, limiting current predictions regarding the diastereoselectivity of these reactions. The intramolecular cycloaddition of an asymmetric P-nitroso phosphine oxide (19) for the first time produces a unique phosphorus-containing heterocyclic compound (20).

  DOI：

  10.1021/jo0202839

文献信息

• Diastereoselective and Intramolecular Cycloadditions of Asymmetric <i>P-</i>Nitroso Phosphine Oxides
  作者：Roy W. Ware、Cynthia S. Day、S. Bruce King

  DOI：10.1021/jo0202839

  日期：2002.8.1

  Benzyl phenyl P-nitroso phosphine oxide (5) reacts as an N-O heterodienophile with 1,3-cyclopentadiene to give the diastereomeric cycloadducts 6a,b in a ratio of 1.5:1 (6a:6b). The same reaction in the presence of tin tetrachloride produces 6a,b in a ratio of 2.9:1 (6a:6b). Cycloaddition of the structurally modified P-nitroso phosphine oxide (18) with 1,3-cyclopentadiene forms the diastereomeric cycloadducts 16a,b in a ratio of 3.1:1 (16a:16b). These results suggest the reactions of these P-nitroso phosphine oxides and 1,3-cyclopentadiene occur through a transition state where the heterodienophile adopts an s-cis conformation and approaches the diene in an exo fashion syn to the phenyl group. This model resembles those proposed for the cycloadditions of the structurally similar asymmetric vinyl phosphine oxides. Reaction of 18 with 1,3-cyclopentadiene in the presence of a Lewis acid produces cycloadducts 16ab in a ratio of 7:1 (16a:16b), which approaches synthetic utility. Similar experiments show that 1,3-cyclohexadiene likely reacts with P-nitroso phosphine oxides through a different transition state, limiting current predictions regarding the diastereoselectivity of these reactions. The intramolecular cycloaddition of an asymmetric P-nitroso phosphine oxide (19) for the first time produces a unique phosphorus-containing heterocyclic compound (20).