(+/-)-N-benzoyl-α-vinylalanine methyl ester | 74761-84-5

• 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: (+/-)-N-benzoyl-α-vinylalanine methyl ester
• 英文别名: (+/-)-N-benzoyl-α-vunylalanine methyl ester；methyl N-benzoyl-α-vinylalaninate；2-Benzoylamino-2-methylbut-3-enoic acid, methyl ester；methyl 2-benzamido-2-methylbut-3-enoate
• CAS: 74761-84-5
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: BQRLGHSQEDEJDB-UHFFFAOYSA-N

物化性质

• 沸点：
  410.2±38.0 °C(Predicted)
• 密度：
  1.105±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-N-benzoyl-α-vinylalanine methyl ester 在 臭氧 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 (+/-)-methyl N-benzoyl-α-(E)-(2'-fluoro-2'-benzenesulfonyl)vinylalaninate
  参考文献：
  名称：

  Synthesis of Quaternary Amino Acids Bearing a (2‘Z)-Fluorovinyl α-Branch:  Potential PLP Enzyme Inactivators

  摘要：

  Protected alpha-formyl amino acids, themselves available from the corresponding a-vinyl amino acids, are stereoselectively transformed into the (Z)-configured alpha-(2'-fluoro)vinyl amino acids via a three-step sequence. The route employs McCarthy's reagent, diethyl alpha-fluoro-alpha-(phenylsulfonyl)methyl phosphonate, and proceeds via the intermediate (E)-alpha-fluorovinyl sulfones and (E)-alpha-fluorovinyistannanes. The latter may either be exploited as novel cross-coupling partners for fluorovinyl branch extension or be globally deprotected, to provide the title compounds.

  DOI：

  10.1021/ol049422u
• 作为产物：
  描述：

  4-((E)-2-Benzenesulfonyl-vinyl)-4-methyl-2-phenyl-4H-oxazol-5-one 在 aluminium amalgam 、 三乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 生成 (+/-)-N-benzoyl-α-vinylalanine methyl ester
  参考文献：
  名称：

  Überführung von α-Aminosäuren in α-Vinylaminosäuren

  摘要：

  DOI：

  10.1055/s-1980-29063

文献信息

• A new retro-aza-ene reaction: formal reductive amination of an α-keto acid to an α-amino acid
  作者：David B. Berkowitz、W. Bernd Schweizer

  DOI：10.1016/s0040-4020(01)88730-5

  日期：1992.2

  Two diastereomeric reductive amination reagents, 1a and 1b, were synthesized. Each reagent was condensed with ethyl pyruvate as a model alpha-keto acid. Flash vacuum pyrolysis of the pyruvate adducts, 10a and 10b, results in cheleotropic elimination of CO, followed by a new type of retro-aza-ene reaction. A molecule of benzene and a protected alanine derivative, 11, are produced in the retro-ene reaction. This sequence constitutes the first formal reductive amination of an alpha-keto acid via a thermal rearrangement. Diastereomer 10b undergoes the rearrangement more readily than diastereomer 10a, indicating that an exo transition state is preferred over an endo transition state for this particular retro-aza-ene reaction.
• Pedersen, Michelle L.; Berkowitz, David B., Journal of Organic Chemistry, 1993, vol. 58, # 25, p. 6965 - 6975
  作者：Pedersen, Michelle L.、Berkowitz, David B.

  DOI：——

  日期：——
• Berkowitz, David B., Synthetic Communications, 1990, vol. 20, # 12, p. 1819 - 1829
  作者：Berkowitz, David B.

  DOI：——

  日期：——
• BERKOWITZ, DAVID B., SYNTH. COMMUN., 20,(1990) N2, C. 1819-1829
  作者：BERKOWITZ, DAVID B.

  DOI：——

  日期：——
• Synthesis of Quaternary Amino Acids Bearing a (2‘Z)-Fluorovinyl α-Branch:  Potential PLP Enzyme Inactivators
  作者：David B. Berkowitz、Roberto de la Salud-Bea、Wan-Jin Jahng

  DOI：10.1021/ol049422u

  日期：2004.5.1

  Protected alpha-formyl amino acids, themselves available from the corresponding a-vinyl amino acids, are stereoselectively transformed into the (Z)-configured alpha-(2'-fluoro)vinyl amino acids via a three-step sequence. The route employs McCarthy's reagent, diethyl alpha-fluoro-alpha-(phenylsulfonyl)methyl phosphonate, and proceeds via the intermediate (E)-alpha-fluorovinyl sulfones and (E)-alpha-fluorovinyistannanes. The latter may either be exploited as novel cross-coupling partners for fluorovinyl branch extension or be globally deprotected, to provide the title compounds.