(Z)-1-Benzoyl-4-cyclohexyl-2,2-diphenyl-3-<(Z)-1,2-bis(methoxycarbonyl)vinyl>-1,5-diaza-2λ⁵-phosphapenta-1,3-diene | 155728-64-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (Z)-1-Benzoyl-4-cyclohexyl-2,2-diphenyl-3-<(Z)-1,2-bis(methoxycarbonyl)vinyl>-1,5-diaza-2λ⁵-phosphapenta-1,3-diene
• 英文别名: dimethyl (E)-2-[(Z)-2-amino-1-[benzoylimino(diphenyl)-lambda5-phosphanyl]-2-cyclohexylethenyl]but-2-enedioate；dimethyl (E)-2-[(Z)-2-amino-1-[benzoylimino(diphenyl)-λ5-phosphanyl]-2-cyclohexylethenyl]but-2-enedioate
• CAS: 155728-64-6
• 化学式: C₃₃H₃₅N₂O₅P
• 分子量: 570.625
• InChiKey: ROMDQBVDAVMOQP-WGDUTUNQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  41
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (Z)-1-Benzoyl-4-cyclohexyl-2,2-diphenyl-3-<(Z)-1,2-bis(methoxycarbonyl)vinyl>-1,5-diaza-2λ⁵-phosphapenta-1,3-diene 以 二氯甲烷 为溶剂， 反应 12.0h， 以90%的产率得到Methyl (E)-{4-[benzoylimino(diphenyl)-λ⁵-phosphanyl]-5-cyclohexyl-2-oxo-2,3-dihydropyrrol-3-ylidene}acetate
  参考文献：
  名称：

  由β-[（N-酰基）磷腈基]烯胺和乙酰二甲基二甲酯二甲酸酯合成4-磷烯基-2,3-二氢吡咯-2-酮和5-磷烯基-2-吡啶酮

  摘要：

  通过将乙炔二羧酸二甲酯加到[（N-酰基）磷腈基]烯胺上，可以得到4-磷烯基-2，3-二氢吡咯-2-酮和5-磷烯基-2-吡啶酮。在回流的二氯甲烷中，反应仅提供2，3-二氢吡咯-2-酮，而在甲苯中，在110℃下，形成2-吡啶酮和2，3-二氢吡咯-2-酮的混合物。它们容易通过分级重结晶分离。基于二维1 H，13 C相关性和稳态核Overhauser增强实验，明确分配了所有新化合物的结构。对于2-吡啶酮，已经确定了4 J PH的绝对符号。

  DOI：

  10.1039/p19960001481
• 作为产物：
  描述：

  丁炔二酸二甲酯 、 N-[[(Z)-2-amino-2-cyclohexylethenyl]-diphenyl-lambda5-phosphanylidene]benzamide 以 二氯甲烷 为溶剂， 反应 36.0h， 以80%的产率得到(E)-1-Benzoyl-4-cyclohexyl-2,2-diphenyl-3-<(Z)-1,2-bis(methoxycarbonyl)vinyl>-1,5-diaza-2λ⁵-phosphapenta-1,3-diene
  参考文献：
  名称：

  Synthesis of Polyfunctionalized 1-Aminobuta-1,3-dienes by Addition of Dimethyl Acetylenedicarboxylate to (Z)-.beta.-Enamino-.lambda.5-Phosphazenes. Configurational and Conformational Analysis Based on NOE Data, nJPX Coupling Constant, X-ray Structures, and Semiempirical Calculations

  摘要：

  DMAD adds regioselectivelly to N-acyl-(Z)-beta-enaminophosphazenes through the beta position with high stereoselectivity. The stereochemistry and conformation of the products 2 and 4 in solution have been elucidated based upon NOE experiments and (n)J(PX) (n = 1-4, X = C, H) data. Large negative (4)J(PH) coupling constants from a predominant n contribution were observed from which conformational information could be derived. (3)J(PC) values are positive and follow the expected Karplus model, and values (2)J(PC) show a large stereochemical dependence. The activation energies for the isomerization of the C=C double bond as well as for the rotation around the C-N single bond of he enamine linkage have been calculated. The crystal structures of (Z)-1-benzoyl-3-[(Z)-1,2-bis-(methoxycarbonyl)vinyl]-2,2-diphenyl-4-(p-tolyl)-1,5-diaza-2 lambda(5)-phosphapenta-1,3-diene (2a) [P2(1)/ c, a = 15.332(6) Angstrom A, b = 17.154(4) Angstrom A, c = 12.127(3) Angstrom A, beta = 101.40(3)degrees, Z = 4] and (E)-1-benzoyl-3-[(Z)-1,2-bis(methoxycarbonyl)vinyl]-2,2-diphenyl-4-cyclohexyl-1,5-diaza-2 lambda(5)-phosphapenta-1,3-diene (2d) [P2(1)/c, a = 12.167(7) Angstrom A, b = 21.14(4) Angstrom A, c 12.845(7) Angstrom A, beta = 108.77(6)degrees, Z = 4] have been elucidated by single-crystal X-ray diffraction. Calculated conformations by MM and PM3 methods were in good agreement with the experimental observations.

  DOI：

  10.1021/jo00087a010