Methyl (Z)-N-(Diphenylmethylene)-α,β-didehydro-β-phenylalaninate | 130740-31-7

• 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: Methyl (Z)-N-(Diphenylmethylene)-α,β-didehydro-β-phenylalaninate
• 英文别名: (Z)-Cinnamic acid, 2-diphenylmethyleneamino-,methyl ester；methyl (Z)-2-(benzhydrylideneamino)-3-phenylprop-2-enoate
• CAS: 130740-31-7
• 化学式: C₂₃H₁₉NO₂
• 分子量: 341.409
• InChiKey: HSDHQPPXLNLVIE-FXBPSFAMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Methyl (Z)-N-(Diphenylmethylene)-α,β-didehydro-β-phenylalaninate 在 盐酸 作用下， 以 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 90.5h， 生成 (1R,2R)-1-methoxycarbonyl-2-phenylcyclopropanaminium chloride
  参考文献：
  名称：

  Spadoni; Balsamini; Bedini, Il Farmaco, 1993, vol. 48, # 12, p. 1663 - 1674

  摘要：

  DOI：
• 作为产物：
  描述：

  Methyl (E)-N-(Diphenylmethylene)-α,β-didehydro-β-phenylalaninate 反应 1.0h， 以90%的产率得到Methyl (Z)-N-(Diphenylmethylene)-α,β-didehydro-β-phenylalaninate
  参考文献：
  名称：

  Stereospecific Synthesis ofN-(Diphenylmethylene)-α,β-didehydroamino Acid Methyl Esters from β-Hydroxy-α-amino Acids

  摘要：

  通过中间体 N-(二苯基亚甲基)-δ,δ-二羟基氨基酸甲酯 1b-d 以绝对几何选择性从廉价的δ-羟基氨基酸制备出 N-(二苯基亚甲基)-δ-二羟基氨基酸甲酯 2b-d。此外，还可以轻松地从 E 异构体转化为相应的 Z 异构体，从而避免了使用不常见的δ-²-羟基氨基酸作为起始原料。

  DOI：

  10.1055/s-1990-27012

文献信息

• Substituent effects on 1,3-dipolar cycloadditions to some 1,1-diphenyl-2-aza-1,3-butadiene derivatives.
  作者：Cesarino Balsamini、Annalida Bedini、Gilberto Spadoni、Marina Burdisso、Anna Maria Capelli

  DOI：10.1016/s0040-4020(01)90397-7

  日期：1994.3

  The reactivity and in particular the siteselectivity of [3+2] electrocyclic additions to 1,1-diphenyl-2-aza-1,3-butadienes, substituted or not on the terminal carbon with methyl and phenyl, and with a 3-carbomethoxyl group, have been investigated with the 1,3-dipolar reagents 4-nitrobenzonitrile oxide and diazomethane. The role of the 3-carbomethoxy substituent in determining the siteselectivity observed in these reactions is discussed in relation to experimental results and to conformational models of some of the tested 2-azadiene dipolarophiles calculated on AM1 bases.
• Reactions of 3-carbomethoxy-2-aza-1,3-butadiene derivatives with dienophiles
  作者：Cesarino Balsamini、Annalida Bedini、Roberta Galarini、Gilberto Spadoni、Giorgio Tarzia、Mahmoud Hamdan

  DOI：10.1016/s0040-4020(01)89546-6

  日期：1994.1

  The reactions of 1,1-diphenyl-3-carbomethoxy-2-aza-1,3-butadiene derivatives la-e (on C4 : H,H or H,CH3 or H,C6H5, both E and Z isomers), and of the C4 unsubstituted 1-phenyl-1-ethoxy analogue 2, were studied with a number of electron-rich and electron-poor dienophiles, with results showing that la-e give heterocycloadducts in Dlels-Alder reactions with electron-poor dienophiles. Michael adducts were obtained from the EtAlCl(2) catalyzed reactions of these compounds with dimethyl acetylendicarboxylate. Compound 2 gave heterocyclic adducts as well but behaved like a nucleophile, at least in the case of the reactions with dimethyl acetylendicarboxylate and ethyl propynoate: these reactions afforded 2-azatrienes as Michael adducts that gave pyridine derivatives upon heating. The synthesis of the new 1-ethoxy-2-aza-1,3-butadiene 2 is also reported.
• BALSAMINI, CESARINO;DURANTI, ERMANNO;MARIANI, LEONARDO;SALVATORI, AMERICO+, SYNTHESIS,(1990) N, C. 779-781
  作者：BALSAMINI, CESARINO、DURANTI, ERMANNO、MARIANI, LEONARDO、SALVATORI, AMERICO+

  DOI：——

  日期：——
• Balsamini Cesarino, Bedini Annalida, Spadoni Gilberto, Burdisso Marina, C+, Tetrahedron, 50 (1994) N 12, S 3773-3784
  作者：Balsamini Cesarino, Bedini Annalida, Spadoni Gilberto, Burdisso Marina, C+

  DOI：——

  日期：——