(R)-Z-tert-butyl 3-(allylamino)-2-ethylidene-4-methylpentanoate | 1334125-19-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R)-Z-tert-butyl 3-(allylamino)-2-ethylidene-4-methylpentanoate
• CAS: 1334125-19-7
• 化学式: C₁₅H₂₇NO₂
• 分子量: 253.385
• InChiKey: OFAWDCDJOGKLGJ-KIWPFMIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.07
• 重原子数：
  18.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  38.33
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  tert-butyl (Z)-2-[(1S)-1-methoxycarbonyloxyethyl]-4-methylpent-2-enoate 、 丙烯胺 在 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 (5,7-dioxa-6-phosphadibenzo[a,c]cyclohepten-6-yl)dimethylamine 作用下， 以 乙醇 为溶剂， 生成 (R)-Z-tert-butyl 3-(allylamino)-2-ethylidene-4-methylpentanoate
  参考文献：
  名称：

  A straightforward route to enantiopure 2-substituted-3,4-dehydro-β-proline via ring closing metathesis

  摘要：

  The synthesis of unusual cyclic amino acids, that may be envisaged as proline analogs, is an area of great interest for their potential applications as scaffolds for the design of bioactive peptidomimetics or units for the creation of novel foldamers. We have carried out the preparation of cyclic dehydro-beta-amino acids starting from allylic carbonates via a two-step allylic amination/ring closing metathesis (RCM) protocol. The introduction of the allylamino moiety has been carried out either without a catalyst, through an S(N)2' reaction, or in the presence of iridium complexes. The backbone of the allylamino intermediates contains two unsaturations, thus suggesting that RCM could be a valuable tool for the preparation of dihydropyrrole scaffolds. A similar reaction has been already reported in the literature for racemic aromatic-substituted substrates, but no examples of enantiopure derivatives bearing aliphatic chains have been reported. The reaction was optimized by testing different Grubbs' catalysts and carbamate nitrogen protecting groups. Moreover, in view of a future application of these dehydro-beta-amino acids as central core of peptidomimetics, the malonate chain was also used to protect nitrogen prior to RCM.

  DOI：

  10.1007/s00726-011-0921-3