4-(diethoxyphosphinyl)-3-methyl-4H-1,2-benzoxazine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 4-(diethoxyphosphinyl)-3-methyl-4H-1,2-benzoxazine
• 英文别名: 4-diethoxyphosphoryl-3-methyl-4H-1,2-benzoxazine
• 化学式: C₁₃H₁₈NO₄P
• 分子量: 283.264
• InChiKey: AYHPCLPSUSKPDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  57.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  diethyl (2-nitro-1-phenylpropyl)phosphonate 在 sodium hydroxide 、 硫酸 作用下， 生成 4-(diethoxyphosphinyl)-3-methyl-4H-1,2-benzoxazine
  参考文献：
  名称：

  Reactions of ethyl phosphites with .beta.-nitrostyrenes. The role of nitrosoalkenes as intermediates

  摘要：

  3-Phenyl-2-substituted-indoles are formed in high yields in the reaction of Ph2C=C(R)NO2 (R = H, Me, Ph) with (EtO)3P at 150-degrees-C while reaction with (EtO)2PO-/(EtO)2P(O)H at room temperature forms the aziridines 1 with R = H, Me, Ph. 2,2-Diphenyl-3-substituted-2H-azirines formed by deoxygenation of the Michael-type adducts are postulated as intermediates. Reactions of PhCH=C(R)NO2 (R = H, Me, Ph) with (EtO)3P at 150-degrees-C or (EtO)2PO-/(EtO)2P(O)H at room temperature give products resulting from the addition of the phosphorus nudeophile at the benzylidene carbon atom. Evidence for the formartion of cyclic structures with pentacoordinated phosphorus atoms is presented for the reaction of Ph2C=C(Me)NO2 with (EtO)2PO-/EtO)2P(O)H and for PhCH=C(R)NO2 (R = H, Me, Ph) with (EtO)3P. The Michael-type adducts PhCH[P(O)(OEt)2]CH(R)NO2 (R = Me, Ph) undergo reaction upon treatment with aqueous base at 80-100-degrees-C followed by acidification to yield the 3-(diethoxyphosphinyl)-2-R-N-hydroxyindoles. 4-(Diethoxyphosphinyl)-3-R-4H-1,2-benzoxazines (13, R = Me, Ph) are formed by reaction with 85% H2SO4 Of the adducts of PhCH=C(R)NO2 with (EtO)2PO (R = Me) or (EtO)3P (R = Ph).

  DOI：

  10.1021/jo00050a026

文献信息

• Reactions of ethyl phosphites with .beta.-nitrostyrenes. The role of nitrosoalkenes as intermediates
  作者：Glen A. Russell、Ching Fa Yao

  DOI：10.1021/jo00050a026

  日期：1992.11

  3-Phenyl-2-substituted-indoles are formed in high yields in the reaction of Ph2C=C(R)NO2 (R = H, Me, Ph) with (EtO)3P at 150-degrees-C while reaction with (EtO)2PO-/(EtO)2P(O)H at room temperature forms the aziridines 1 with R = H, Me, Ph. 2,2-Diphenyl-3-substituted-2H-azirines formed by deoxygenation of the Michael-type adducts are postulated as intermediates. Reactions of PhCH=C(R)NO2 (R = H, Me, Ph) with (EtO)3P at 150-degrees-C or (EtO)2PO-/(EtO)2P(O)H at room temperature give products resulting from the addition of the phosphorus nudeophile at the benzylidene carbon atom. Evidence for the formartion of cyclic structures with pentacoordinated phosphorus atoms is presented for the reaction of Ph2C=C(Me)NO2 with (EtO)2PO-/EtO)2P(O)H and for PhCH=C(R)NO2 (R = H, Me, Ph) with (EtO)3P. The Michael-type adducts PhCH[P(O)(OEt)2]CH(R)NO2 (R = Me, Ph) undergo reaction upon treatment with aqueous base at 80-100-degrees-C followed by acidification to yield the 3-(diethoxyphosphinyl)-2-R-N-hydroxyindoles. 4-(Diethoxyphosphinyl)-3-R-4H-1,2-benzoxazines (13, R = Me, Ph) are formed by reaction with 85% H2SO4 Of the adducts of PhCH=C(R)NO2 with (EtO)2PO (R = Me) or (EtO)3P (R = Ph).