(4S)-4-[[(benzyloxy)carbonyl]amino]-3-oxo-5-phenyl-2-triphenylphosphoranylidene-pentanenitrile | 214122-05-1

• 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: (4S)-4-[[(benzyloxy)carbonyl]amino]-3-oxo-5-phenyl-2-triphenylphosphoranylidene-pentanenitrile
• 英文别名: (4S)-4-(benzyloxycarbonylamino)-3-oxo-5-phenyl-2-(triphenylphosphoranylidene)pentanenitrile；benzyl N-[(2S)-4-cyano-3-oxo-1-phenyl-4-(triphenyl-lambda5-phosphanylidene)butan-2-yl]carbamate；benzyl N-[(2S)-4-cyano-3-oxo-1-phenyl-4-(triphenyl-λ5-phosphanylidene)butan-2-yl]carbamate
• CAS: 214122-05-1
• 化学式: C₃₇H₃₁N₂O₃P
• 分子量: 582.638
• InChiKey: IYENMNQAPBSATG-UMSFTDKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  43
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  79.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S)-4-[[(benzyloxy)carbonyl]amino]-3-oxo-5-phenyl-2-triphenylphosphoranylidene-pentanenitrile 在 氢溴酸 作用下， 以 溶剂黄146 为溶剂， 反应 5.0h， 以72%的产率得到(2RS)-5-amino-2-benzyl-4-triphenylphosphonio-2,4-dihydropyrrol-3-one bromide
  参考文献：
  名称：

  Triphenylphosphoranylidene Substituted Heterocycles as Versatile Intermediates

  摘要：

  DOI：

  10.3987/com-08-s(f)12
• 作为产物：
  描述：

  N-苄氧羰基-L-苯丙氨酸 、 (三苯基膦)乙腈 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到(4S)-4-[[(benzyloxy)carbonyl]amino]-3-oxo-5-phenyl-2-triphenylphosphoranylidene-pentanenitrile
  参考文献：
  名称：

  (Cyanomethylene)phosphoranes as Novel Carbonyl 1,1-Dipole Synthons: An Efficient Synthesis of .alpha.-Keto Acids, Esters, and Amides

  摘要：

  Carboxylic acids react with (cyanomethylene)triphenylphosphorane in the presence of EDCI to form cyano keto phosphoranes. The resulting ylides may then be oxidatively cleaved with ozone to form alpha,beta-diketonitriles. These highly electrophilic products may then be converted in situ to alpha-keto acids, esters, and amides.

  DOI：

  10.1021/jo00095a005

文献信息

• Synthesis of cyanoketophosphoranes, precursors of β-amino-α-keto-esters from UNCAs
  作者：Marielle Paris、Catherine Pothion、Christine Michalak、Jean Martinez、Jean-Alain Fehrentz

  DOI：10.1016/s0040-4039(98)01504-4

  日期：1998.9

  Cyanomethylene triphenylphosphoranes of N-protected amino acids were synthesized from the corresponding N-urethane protected α-amino acid N-carboxyanhydrides (UNCAs) by reaction with cyanomethyltriphenylphosphonium chloride in good yields. These compounds are precursors of α-keto esters which are candidates for mimicking the tetrahedric transition state in enzyme inhibitors.

  由N-氨基甲酸酯保护的α-氨基酸N-羧基酸酐（UNCA）通过与氰基甲基三苯基chloride氯化物反应，以高收率合成了N-保护氨基酸的氰基亚甲基三苯基膦。这些化合物是α-酮酯的前体，它们是模拟酶抑制剂中四面体过渡态的候选物。
• (Cyanomethylene)phosphoranes as Novel Carbonyl 1,1-Dipole Synthons: An Efficient Synthesis of .alpha.-Keto Acids, Esters, and Amides
  作者：Harry H. Wasserman、Wen-Bin Ho

  DOI：10.1021/jo00095a005

  日期：1994.8

  Carboxylic acids react with (cyanomethylene)triphenylphosphorane in the presence of EDCI to form cyano keto phosphoranes. The resulting ylides may then be oxidatively cleaved with ozone to form alpha,beta-diketonitriles. These highly electrophilic products may then be converted in situ to alpha-keto acids, esters, and amides.
• Wasserman Harry H., Ho Wen-Bin, J. Org. Chem, 59 (1994) N 16, S 4364-4366
  作者：Wasserman Harry H., Ho Wen-Bin

  DOI：——

  日期：——
• Triphenylphosphoranylidene Substituted Heterocycles as Versatile Intermediates
  作者：Alan R. Katritzky、Adam S. Vincek、Peter J. Steel

  DOI：10.3987/com-08-s(f)12

  日期：——
• Azobenzene-Containing, Peptidyl α-Ketoesters as Photobiological Switches of α-Chymotrypsin
  作者：Andrew J Harvey、Andrew D Abell

  DOI：10.1016/s0040-4020(00)00883-8

  日期：2000.12

  Three photoswitchable, peptidomimetic inhibitors of oc-chymotrypsin have been synthesised. The compounds comprise an azobenzene, an alpha -ketoester and L-phenylalanine. The compounds were photoisomerised to give enriched states of the (E) and (Z) isomers and these states were assayed against alpha -chymotrypsin. The inhibitors were shown to be moderately active with switching ability of between two- and three-fold between the two isomer-enriched states. The behaviour of the inhibitors in solution was examined; specifically, their hydration and configurational stability. (C) 2000 Elsevier Science Ltd. All rights reserved.