(Z)-methyl 2-((tert-butoxycarbonyl)amino)-3-(3,5-di-tert-butylphenyl)acrylate | 1564245-63-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (Z)-methyl 2-((tert-butoxycarbonyl)amino)-3-(3,5-di-tert-butylphenyl)acrylate
• 英文别名: methyl (Z)-3-(3,5-ditert-butylphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]prop-2-enoate
• CAS: 1564245-63-1
• 化学式: C₂₃H₃₅NO₄
• 分子量: 389.535
• InChiKey: PLEHWUZIRJMTAY-AQTBWJFISA-N

物化性质

• 熔点：
  127.5-128.2 °C
• 沸点：
  461.0±45.0 °C(predicted)
• 密度：
  1.029±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-methyl 2-((tert-butoxycarbonyl)amino)-3-(3,5-di-tert-butylphenyl)acrylate 、 联硼酸频那醇酯 在 (S,Sp)-ip-FOXAP 、 copper(l) chloride 、 sodium t-butanolate 、 甲醇 作用下， 以 甲苯 为溶剂， 反应 2.5h， 以45%的产率得到(2R,3R)-methyl 2-((tert-butoxycarbonyl)amino)-3-(3,5-di-tert-butylphenyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate
  参考文献：
  名称：

  Copper-Catalyzed Asymmetric Hydroboration of α-Dehydroamino Acid Derivatives: Facile Synthesis of Chiral β-Hydroxy-α-amino Acids

  摘要：

  The Cu-catalyzed asymmetric conjugate hydroboration reaction of beta-substituted alpha-dehydroamino acid derivatives has been established, affording enantioenriched syn- and anti-beta-boronate-alpha-amino acid derivatives with excellent combined yields (83-99%, dr approximate to 1:1) and excellent enantioselectivities (92-98% ee). The hydroboration products were expediently converted into valuable beta-hydroxy-alpha-amino acid derivatives, which were widely used in the preparation of chiral drugs and bioactive molecules.

  DOI：

  10.1021/ol500219e
• 作为产物：
  描述：

  3,5-双(叔丁基)苯甲醛 、 trimethyl 2-(tert-butoxycarbonylamino)phosphonoacetate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到(Z)-methyl 2-((tert-butoxycarbonyl)amino)-3-(3,5-di-tert-butylphenyl)acrylate
  参考文献：
  名称：

  Copper-Catalyzed Asymmetric Hydroboration of α-Dehydroamino Acid Derivatives: Facile Synthesis of Chiral β-Hydroxy-α-amino Acids

  摘要：

  The Cu-catalyzed asymmetric conjugate hydroboration reaction of beta-substituted alpha-dehydroamino acid derivatives has been established, affording enantioenriched syn- and anti-beta-boronate-alpha-amino acid derivatives with excellent combined yields (83-99%, dr approximate to 1:1) and excellent enantioselectivities (92-98% ee). The hydroboration products were expediently converted into valuable beta-hydroxy-alpha-amino acid derivatives, which were widely used in the preparation of chiral drugs and bioactive molecules.

  DOI：

  10.1021/ol500219e

文献信息

• Copper-Catalyzed Asymmetric Hydroboration of α-Dehydroamino Acid Derivatives: Facile Synthesis of Chiral β-Hydroxy-α-amino Acids
  作者：Zhi-Tao He、Yi-Shuang Zhao、Ping Tian、Chuan-Chuan Wang、Han-Qing Dong、Guo-Qiang Lin

  DOI：10.1021/ol500219e

  日期：2014.3.7

  The Cu-catalyzed asymmetric conjugate hydroboration reaction of beta-substituted alpha-dehydroamino acid derivatives has been established, affording enantioenriched syn- and anti-beta-boronate-alpha-amino acid derivatives with excellent combined yields (83-99%, dr approximate to 1:1) and excellent enantioselectivities (92-98% ee). The hydroboration products were expediently converted into valuable beta-hydroxy-alpha-amino acid derivatives, which were widely used in the preparation of chiral drugs and bioactive molecules.