(Z)-<β-(N-benzylcarbamoyl)vinyl>iminophosphorane | 147151-47-1

• 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: (Z)-<β-(N-benzylcarbamoyl)vinyl>iminophosphorane
• 英文别名: (Z)-N-benzyl-3-[(triphenyl-lambda5-phosphanylidene)amino]prop-2-enamide；(Z)-N-benzyl-3-[(triphenyl-λ5-phosphanylidene)amino]prop-2-enamide
• CAS: 147151-47-1
• 化学式: C₂₈H₂₅N₂OP
• 分子量: 436.493
• InChiKey: FOZJCRVCHFHYEL-DQRAZIAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  trans-2-cyclodecen-1-one 、 (Z)-<β-(N-benzylcarbamoyl)vinyl>iminophosphorane 在 palladium on activated charcoal 作用下， 以 xylene 为溶剂， 反应 48.0h， 以5%的产率得到5-(N-benzylcarbamoyl)<7>(2,4)pyridinophane
  参考文献：
  名称：

  Syntheses and properties of 5-substituted [n](2,4)pyridinophanes, model compounds of NAD(P)

  摘要：

  [n](2,4)Pyridinophane derivatives 5-8 having an ester or an amide group at the 5-position were synthesized by aza-Wittig reactions between beta-substituted vinyliminophosphoranes and cyclic alpha,beta-unsaturated ketones. [beta-(Methoxycarbonyl)vinyl]- (1), [beta-(N,N-tetramethylenecarbamoyl)vinyl]-(2), [beta-(N-benzylcarbamoyl)vinyl]-(3), and (beta-carbamoylvinyl)iminophosphorane (4) were synthesized from the corresponding vinyl azides and triphenylphosphine. The heptamethylene chains of 5-(methoxycarbonyl)[7](2,4)pyridinophane (5),5-(N,N-tetramethylenecarbamoyl)[7](2,4)pyridinophane (6), and 5-(N-benzylcarbamoyl)[7](2,4)pyridinophane (7) flipped with AG(double dagger) = 11.2 (T(c) = 10.3-degrees-C), 10.8 (T(c) = 0.2-degrees-C), and 10.5 kcal/mol (T(c) = -5.2-degrees-C), respectively. At lower temperatures, the three conformations of the heptamethylene bridge were frozen. Methylpyridinium iodides 10 (n = 7, 6, and 5) derived from 6 were reduced more easily [E1/2* (half height potential) = -1.65 V (n = 7); -1.63 V (n = 6); -1.29 V vs Ag/AgCl (n = 5)] than the reference compound, 2,4-diethyl-5-(N,N-tetramethylenecarbamoyl)pyridinium ion (11) [E1/2* = -1.82 V vs Ag/AgCl]. The reduced species dimerized quickly.

  DOI：

  10.1021/jo00060a018
• 作为产物：
  描述：

  (E)-N-benzyl-3-chloropropenamide 在 sodium azide 作用下， 以 乙醚 、 二甲基亚砜 为溶剂， 反应 12.0h， 生成 (Z)-<β-(N-benzylcarbamoyl)vinyl>iminophosphorane
  参考文献：
  名称：

  Syntheses and properties of 5-substituted [n](2,4)pyridinophanes, model compounds of NAD(P)

  摘要：

  [n](2,4)Pyridinophane derivatives 5-8 having an ester or an amide group at the 5-position were synthesized by aza-Wittig reactions between beta-substituted vinyliminophosphoranes and cyclic alpha,beta-unsaturated ketones. [beta-(Methoxycarbonyl)vinyl]- (1), [beta-(N,N-tetramethylenecarbamoyl)vinyl]-(2), [beta-(N-benzylcarbamoyl)vinyl]-(3), and (beta-carbamoylvinyl)iminophosphorane (4) were synthesized from the corresponding vinyl azides and triphenylphosphine. The heptamethylene chains of 5-(methoxycarbonyl)[7](2,4)pyridinophane (5),5-(N,N-tetramethylenecarbamoyl)[7](2,4)pyridinophane (6), and 5-(N-benzylcarbamoyl)[7](2,4)pyridinophane (7) flipped with AG(double dagger) = 11.2 (T(c) = 10.3-degrees-C), 10.8 (T(c) = 0.2-degrees-C), and 10.5 kcal/mol (T(c) = -5.2-degrees-C), respectively. At lower temperatures, the three conformations of the heptamethylene bridge were frozen. Methylpyridinium iodides 10 (n = 7, 6, and 5) derived from 6 were reduced more easily [E1/2* (half height potential) = -1.65 V (n = 7); -1.63 V (n = 6); -1.29 V vs Ag/AgCl (n = 5)] than the reference compound, 2,4-diethyl-5-(N,N-tetramethylenecarbamoyl)pyridinium ion (11) [E1/2* = -1.82 V vs Ag/AgCl]. The reduced species dimerized quickly.

  DOI：

  10.1021/jo00060a018

文献信息

• Syntheses and properties of 5-substituted [n](2,4)pyridinophanes, model compounds of NAD(P)
  作者：Tadayoshi Oikawa、Nobuhiro Kanomata、Masaru Tada

  DOI：10.1021/jo00060a018

  日期：1993.4

  [n](2,4)Pyridinophane derivatives 5-8 having an ester or an amide group at the 5-position were synthesized by aza-Wittig reactions between beta-substituted vinyliminophosphoranes and cyclic alpha,beta-unsaturated ketones. [beta-(Methoxycarbonyl)vinyl]- (1), [beta-(N,N-tetramethylenecarbamoyl)vinyl]-(2), [beta-(N-benzylcarbamoyl)vinyl]-(3), and (beta-carbamoylvinyl)iminophosphorane (4) were synthesized from the corresponding vinyl azides and triphenylphosphine. The heptamethylene chains of 5-(methoxycarbonyl)[7](2,4)pyridinophane (5),5-(N,N-tetramethylenecarbamoyl)[7](2,4)pyridinophane (6), and 5-(N-benzylcarbamoyl)[7](2,4)pyridinophane (7) flipped with AG(double dagger) = 11.2 (T(c) = 10.3-degrees-C), 10.8 (T(c) = 0.2-degrees-C), and 10.5 kcal/mol (T(c) = -5.2-degrees-C), respectively. At lower temperatures, the three conformations of the heptamethylene bridge were frozen. Methylpyridinium iodides 10 (n = 7, 6, and 5) derived from 6 were reduced more easily [E1/2* (half height potential) = -1.65 V (n = 7); -1.63 V (n = 6); -1.29 V vs Ag/AgCl (n = 5)] than the reference compound, 2,4-diethyl-5-(N,N-tetramethylenecarbamoyl)pyridinium ion (11) [E1/2* = -1.82 V vs Ag/AgCl]. The reduced species dimerized quickly.