ethyl (Z,4S)-4-(dibenzylamino)-2-formamido-5-phenylpent-2-enoate | 143250-58-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl (Z,4S)-4-(dibenzylamino)-2-formamido-5-phenylpent-2-enoate
• CAS: 143250-58-2
• 化学式: C₂₈H₃₀N₂O₃
• 分子量: 442.558
• InChiKey: KVLLHLRHJFNPCU-XCUSKGCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (Z,4S)-4-(dibenzylamino)-2-formamido-5-phenylpent-2-enoate 生成 (1S,2S)-2-((S)-1-Dibenzylamino-2-phenyl-ethyl)-1-formylamino-cyclopropanecarboxylic acid ethyl ester
  参考文献：
  名称：

  Reetz, Manfred T., Angewandte Chemie, 1991, vol. 103, # 12, p. 1559 - 1573

  摘要：

  DOI：
• 作为产物：
  描述：

  异氰基乙酸乙酯 、 苯丙醛,a-[二(苯基甲基)氨基]-,(S)- 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 生成 ethyl (Z,4S)-4-(dibenzylamino)-2-formamido-5-phenylpent-2-enoate 、
  参考文献：
  名称：

  Cycloaddition reactions of λ-amino α,β-didehydro amino acid esters: a test case for the principle of 1,3-allylic strain

  摘要：

  N,N-Dibenzylainino aldehydes, readily accessible from amino acids, can be converted into gamma-N,N-dibenzylamino alpha,beta-didehydro amino acid esters without racemization; these undergo stereoselective Diels-Alder reactions and 1,3-dipolar cycloaddition with diazomethane, the sense of diastereoselectivity being opposite to that predicted by the conventional principle of 1,3-allylic strain.

  DOI：

  10.1016/s0040-4039(00)92661-3

文献信息

• Stereoselective synthesis of α,γ -diamino acid esters
  作者：Manfred T. Reetz、Frank Kayser

  DOI：10.1016/0957-4166(92)80010-t

  日期：1992.11

  Chiral didehydro amino acid esters 2/3 derived from amino acids are hydrogenated stereoselectively with rhodium catalysts based on achiral ligands, the alpha,gamma-diamino acid derivatives 4 being the major products. The sense and degree of stereoselectivity can be influenced to some extent by the use of chiral diphosphines. The iridium-containing Crabtree-catalyst is particularly effective in the case of the serine derivative 2 (R1 = HOCH2).
• Cycloaddition reactions of λ-amino α,β-didehydro amino acid esters: a test case for the principle of 1,3-allylic strain
  作者：Manfred T Reetz、Frank Kayser、Klaus Harms

  DOI：10.1016/s0040-4039(00)92661-3

  日期：1992.6

  N,N-Dibenzylainino aldehydes, readily accessible from amino acids, can be converted into gamma-N,N-dibenzylamino alpha,beta-didehydro amino acid esters without racemization; these undergo stereoselective Diels-Alder reactions and 1,3-dipolar cycloaddition with diazomethane, the sense of diastereoselectivity being opposite to that predicted by the conventional principle of 1,3-allylic strain.
• Reetz, Manfred T., Angewandte Chemie, 1991, vol. 103, # 12, p. 1559 - 1573
  作者：Reetz, Manfred T.

  DOI：——

  日期：——