ethyl 2-[(S)-allyl(1-phenylethyl)amino]pent-4-enoate | 1258422-16-0

• 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: ethyl 2-[(S)-allyl(1-phenylethyl)amino]pent-4-enoate
• 英文别名: ethyl 2-{allyl[(S)-1-phenylethyl]amino}pent-4-enoate；ethyl 2-[[(1S)-1-phenylethyl]-prop-2-enylamino]pent-4-enoate
• CAS: 1258422-16-0
• 化学式: C₁₈H₂₅NO₂
• 分子量: 287.402
• InChiKey: QVHIWYPOLFQHAR-MYJWUSKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2-[(S)-allyl(1-phenylethyl)amino]pent-4-enoate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 titanium(IV) tetraethanolate 、 5%-palladium/activated carbon 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (s)-哌啶-2-羧酸乙酯盐酸盐
  参考文献：
  名称：

  Synthesis of enantiopure cyclic amino acid derivatives via a sequential diastereoselective Petasis reaction/ring closing olefin metathesis process

  摘要：

  A novel approach to the synthesis of enantiopure cyclic amino esters is reported. The utilization of allyl-boronic acid together with (S)-alpha-methylbenzylamine as a chiral auxiliary in the Petasis/Mannich reaction led to the formation of allylglycine derivatives in good yield and with high diastereoselectivity. Subsequent esterification, N-allylation followed by ring-closing metathesis (RCM) reaction enabled the preparation of enantiomerically pure cyclic a-amino acid derivatives. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2017.01.001
• 作为产物：
  描述：

  N-[(S)-1-phenylethyl]pent-4-enoic acid 在 氯化亚砜 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 ethyl 2-[(S)-allyl(1-phenylethyl)amino]pent-4-enoate
  参考文献：
  名称：

  Synthesis of enantiopure cyclic amino acid derivatives via a sequential diastereoselective Petasis reaction/ring closing olefin metathesis process

  摘要：

  A novel approach to the synthesis of enantiopure cyclic amino esters is reported. The utilization of allyl-boronic acid together with (S)-alpha-methylbenzylamine as a chiral auxiliary in the Petasis/Mannich reaction led to the formation of allylglycine derivatives in good yield and with high diastereoselectivity. Subsequent esterification, N-allylation followed by ring-closing metathesis (RCM) reaction enabled the preparation of enantiomerically pure cyclic a-amino acid derivatives. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2017.01.001

文献信息

• Synthesis of non-natural cyclic amino acids from available unsaturated tertiary amines
  作者：I. D. Titanyuk、I. P. Beletskaya

  DOI：10.1134/s1070428010090022

  日期：2010.9

  New approach is developed to the synthesis of cyclic amino acids derivatives. Unsaturated tertiary amines react with ethyl diazoacetate under the catalysis by copper catalyst Cu(F3acac)2 leading to the formation of products of [2,3]-sigmatropic rearrangement which via the metathesis of double bonds undergo a ring closure. The subsequent hydrogenation of compounds obtained furnished esters of 6- and

  开发了合成环状氨基酸衍生物的新方法。在铜催化剂Cu（F 3 acac）2的催化下，不饱和叔胺与重氮乙酸乙酯反应，导致形成[2,3]-σ重排的产物，该产物通过双键的复分解而闭环。随后获得的化合物的氢化提供了6元和7元环状α-氨基酸的酯。除外消旋外，还获得旋光化合物，特别是（R）-和（S）-哌酸的酯。