Ethyl (E)-2-(N-benzoylamino)-3-bromo-4(S),5(R)-bis<(p-methoxybenzyl)oxy>-5--2-pentenoate | 139427-61-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: Ethyl (E)-2-(N-benzoylamino)-3-bromo-4(S),5(R)-bis<(p-methoxybenzyl)oxy>-5--2-pentenoate
• 英文别名: ethyl (E,4S,5R)-2-benzamido-3-bromo-5-[(2S)-1-[(4-methoxyphenyl)-diphenylmethyl]aziridin-2-yl]-4,5-bis[(4-methoxyphenyl)methoxy]pent-2-enoate
• CAS: 139427-61-5
• 化学式: C₅₂H₅₁BrN₂O₈
• 分子量: 911.89
• InChiKey: NQTJATKBNFZTIN-FIFRXBRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.46
• 重原子数：
  63.0
• 可旋转键数：
  20.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  104.56
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  Ethyl (E)-2-(N-benzoylamino)-3-bromo-4(S),5(R)-bis<(p-methoxybenzyl)oxy>-5--2-pentenoate 在 三乙胺 、 三氯乙酸 作用下， 以 氘代乙腈 为溶剂， 反应 16.75h， 生成 Ethyl 2-(N-Benzoylamino)-2(E)-<3(R),4(R)-bis<(p-methoxybenzyl)oxy>-5(S)-1-azabicyclo<3.1.0>hex-2-ylidene>acetate
  参考文献：
  名称：

  Dehydroamino acid derivatives from D-arabinose and L-serine: synthesis of models for the azinomycin antitumor antibiotics

  摘要：

  Synthesis of aldehydes 17 from D-arabinose and 31 from L-serine provided key precursors for the generation of highly functionalized dehydroamino acid derivatives upon condensation with glycyl phosphonates. Subsequent bromination and intramolecular addition/elimination afforded the azabicyclo[3.1.0]hex-2-ylidene ring system postulated to exist in the azinomycin antitumor antibiotics.

  DOI：

  10.1021/jo00079a033
• 作为产物：
  描述：

  Ethyl N-benzoyl-2-(diethylphosphono)glycinate 在 2,6-二甲基吡啶 、 溴 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正庚烷 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 Ethyl (E)-2-(N-benzoylamino)-3-bromo-4(S),5(R)-bis<(p-methoxybenzyl)oxy>-5--2-pentenoate
  参考文献：
  名称：

  Dehydroamino acid derivatives from D-arabinose and L-serine: synthesis of models for the azinomycin antitumor antibiotics

  摘要：

  Synthesis of aldehydes 17 from D-arabinose and 31 from L-serine provided key precursors for the generation of highly functionalized dehydroamino acid derivatives upon condensation with glycyl phosphonates. Subsequent bromination and intramolecular addition/elimination afforded the azabicyclo[3.1.0]hex-2-ylidene ring system postulated to exist in the azinomycin antitumor antibiotics.

  DOI：

  10.1021/jo00079a033

文献信息

• Stereoselective synthesis of (E)- and (Z)-1-azabicyclo[3.1.0]hex-2-ylidene dehydroamino acid derivatives
  作者：Robert W. Armstrong、John E. Tellew、Edmund J. Moran

  DOI：10.1021/jo00034a002

  日期：1992.4

  Bromination of dehydroamino acid derivatives with NBS or Br2/2,6-lutidine yields (E)- or (Z)-beta-bromo-dehydroamino acid derivatives selectively. Subsequent intramolecular Michael addition-elimination of an aziridine proceeds with complete retention of olefin geometry to provide the 1-azabicyclo[3.1.0]hex-2-ylidene ring system proposed for the azinomycin series of antitumor antibiotics.