methyl 5-amino-2-(difluoromethyl)-2-(phenylmethoxycarbonylamino)pent-3-ynoate | 195195-99-4

• 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: methyl 5-amino-2-(difluoromethyl)-2-(phenylmethoxycarbonylamino)pent-3-ynoate
• CAS: 195195-99-4
• 化学式: C₁₅H₁₆F₂N₂O₄
• 分子量: 326.3
• InChiKey: HHTGGHAUHMIFEH-UHFFFAOYSA-N

物化性质

• 沸点：
  493.2±45.0 °C(Predicted)
• 密度：
  1.295±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.05
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  90.65
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 5-amino-2-(difluoromethyl)-2-(phenylmethoxycarbonylamino)pent-3-ynoate 在 Pd(en)/C 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 Methyl 5-[bis[(2-methylpropan-2-yl)oxycarbonylamino]methylideneamino]-2-(difluoromethyl)-2-(phenylmethoxycarbonylamino)pentanoate
  参考文献：
  名称：

  First Synthesis of Totally Orthogonal Protected α-(Trifluoromethyl)- and α-(Difluoromethyl)arginines

  摘要：

  The first synthesis of a series of totally orthogonal protected racemic alpha-(trifluoromethyl)- and alpha-(difluoromethyl)arginines is described. The key steps of the synthesis are the mild guanidinylation procedure and the selective hydrogenation of a CC triple bond in the presence of a Cbz-group.

  DOI：

  10.1021/jo0009043
• 作为产物：
  描述：

  lithium N,N-bis(trimethylsilyl)aminomethyl acetylide 、 以 四氢呋喃 为溶剂， 以93%的产率得到methyl 5-amino-2-(difluoromethyl)-2-(phenylmethoxycarbonylamino)pent-3-ynoate
  参考文献：
  名称：

  First Synthesis of Totally Orthogonal Protected α-(Trifluoromethyl)- and α-(Difluoromethyl)arginines

  摘要：

  The first synthesis of a series of totally orthogonal protected racemic alpha-(trifluoromethyl)- and alpha-(difluoromethyl)arginines is described. The key steps of the synthesis are the mild guanidinylation procedure and the selective hydrogenation of a CC triple bond in the presence of a Cbz-group.

  DOI：

  10.1021/jo0009043

文献信息

• New efficient syntheses of α-diflyoromethyl- and α-trifluoromethyl-ornithine
  作者：Sergey N. Osipov、Alexander S. Golubev、Norbert Sewald、Klaus Burger

  DOI：10.1016/s0040-4039(97)01344-0

  日期：1997.8

  A new efficient method far the preparation of ornithine derivatives 3-5 is described. The key step of the synthesis is the regioselective alkylation of imine 2 with propargyl amine 1. (C) 1997 Elsevier Science Ltd.
• First Synthesis of Totally Orthogonal Protected α-(Trifluoromethyl)- and α-(Difluoromethyl)arginines
  作者：Maurizio Moroni、Beate Koksch、Sergey N. Osipov、Marcello Crucianelli、Massimo Frigerio、Pierfrancesco Bravo、Klaus Burger

  DOI：10.1021/jo0009043

  日期：2001.1.1

  The first synthesis of a series of totally orthogonal protected racemic alpha-(trifluoromethyl)- and alpha-(difluoromethyl)arginines is described. The key steps of the synthesis are the mild guanidinylation procedure and the selective hydrogenation of a CC triple bond in the presence of a Cbz-group.