3-Diethoxyphosphoryl-1-hydroxy-2-methylindole | 120949-55-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-Diethoxyphosphoryl-1-hydroxy-2-methylindole
• CAS: 120949-55-5
• 化学式: C₁₃H₁₈NO₄P
• 分子量: 283.264
• InChiKey: CAJLJMZFLZCZFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  60.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-Diethoxyphosphoryl-1-hydroxy-2-methylindole 、 碘甲烷 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 10.0h， 以91%的产率得到3-(Diethoxyphosphoryl)-1-methoxy-2-methylindole
  参考文献：
  名称：

  A Facile One-Pot Synthesis of 3-Dialkoxyphosphoryl- and 3-[Alkoxy(phenyl)phosphoryl]-1-hydroxyindoles

  摘要：

  双烷基磷酸酯或烷基苯基磷酸酯与等摩尔量的1-芳基-2-硝基-1-烯烃在醇中与固体碳酸钾共同反应，生成标题化合物，即1-羟基吲哚-3-磷酸酯或-3-磷酸亚酯，产率为57-88%。

  DOI：

  10.1055/s-1990-27020
• 作为产物：
  描述：

  diethyl (2-nitro-1-phenylpropyl)phosphonate 在 sodium hydroxide 作用下， 反应 2.0h， 以79%的产率得到3-Diethoxyphosphoryl-1-hydroxy-2-methylindole
  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

• Yuan, C. Y.; Li, C. Z.; Wang, G. H., Phosphorus, Sulfur and Silicon and the Related Elements, 1993, vol. 75, # 1-4, p. 147 - 150
  作者：Yuan, C. Y.、Li, C. Z.、Wang, G. H.、Huang, W. S.

  DOI：——

  日期：——
• ZHANG, RONGYU;LIAO, XIUGAO;GAO, ZHIFANG, SYNTHESIS (BRD),(1990) N, C. 801-802
  作者：ZHANG, RONGYU、LIAO, XIUGAO、GAO, ZHIFANG

  DOI：——

  日期：——