ethyl 3--amino-4-methyl-2-pentenoate | 170745-53-6

• 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: ethyl 3--amino-4-methyl-2-pentenoate
• 英文别名: ethyl (Z)-4-methyl-3-[[(1R)-1-phenylethyl]amino]pent-2-enoate
• CAS: 170745-53-6
• 化学式: C₁₆H₂₃NO₂
• 分子量: 261.364
• InChiKey: CKIKXXSYKGKCDZ-LKKYZFDUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 3--amino-4-methyl-2-pentenoate 在 palladium dihydroxide 氢气 、 三乙酰氧基硼氢化钠 作用下， 以 甲醇 、 水 、 溶剂黄146 、 乙腈 为溶剂， 反应 4.0h， 生成 (S)-3-Amino-4-methyl-pentanoic acid ethyl ester
  参考文献：
  名称：

  Stereoselective Reduction of Enantiopure β-Enamino Esters by Hydride:  A Convenient Synthesis of Both Enantiopure β-Amino Esters

  摘要：

  The reduction of enantiopure beta-enamino esters 1 with sodium triacetoxyborohydride in acetic acid is described. This occurs with good diastereo- and enantioselectivity to yield beta-amino esters 2 and 3 (after hydrogenolysis of the N-chiral group). A model is reported for the origin of the stereoselectivity through an enol ester-diacetoxyborohydride 6, which affords the intramolecular reduction. By choosing the appropriate chiral amine, this procedure allows a straightforward preparation of both the enantiopure beta-amino esters and derivatives with known biological activity, using readily available starting materials and inexpensive reagents and conditions.

  DOI：

  10.1021/jo960107y
• 作为产物：
  描述：

  [1,2-Dimethyl-prop-(Z)-ylidene]-((R)-1-phenyl-ethyl)-amine 、 碳酸二乙酯 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 以57%的产率得到ethyl 3--amino-4-methyl-2-pentenoate
  参考文献：
  名称：

  烯胺锂与碳酸二乙酯或氯甲酸苄酯的酰化反应获得β-烯胺酯的通用方法

  摘要：

  开发了一种使用易得的起始原料制备β-烯胺酯1的通用方法。使锂化的烯胺与碳酸二乙酯或氯甲酸苄酯反应，形成β-烯氨基酯1a或1b。来自各种各样的酮亚胺和醛亚胺的反应相当普遍。产品包括环状β-烯胺酯1aa-ac，对合成天然产物非常有用。

  DOI：

  10.1016/0040-4020(95)00476-o

文献信息

• Stereoselective Reduction of Enantiopure β-Enamino Esters by Hydride:  A Convenient Synthesis of Both Enantiopure β-Amino Esters
  作者：Cristina Cimarelli、Gianni Palmieri

  DOI：10.1021/jo960107y

  日期：1996.1.1

  The reduction of enantiopure beta-enamino esters 1 with sodium triacetoxyborohydride in acetic acid is described. This occurs with good diastereo- and enantioselectivity to yield beta-amino esters 2 and 3 (after hydrogenolysis of the N-chiral group). A model is reported for the origin of the stereoselectivity through an enol ester-diacetoxyborohydride 6, which affords the intramolecular reduction. By choosing the appropriate chiral amine, this procedure allows a straightforward preparation of both the enantiopure beta-amino esters and derivatives with known biological activity, using readily available starting materials and inexpensive reagents and conditions.
• A versatile route to β-enamino esters by acylation of lithium enamines with diethyl carbonate or benzyl chloroformate
  作者：Giuseppe Bartoli、Cristina Cimarelli、Renato Dalpozzo、Gianni Palmieri

  DOI：10.1016/0040-4020(95)00476-o

  日期：1995.7

  route to β-enamino esters 1, using accessible starting materials, was developed. Lithiated enamines are allowed to react with diethyl carbonate or benzyl chloroformate with the formation of the β-enamino esters 1a or 1b. The reaction is rather general from a wide array of ketimines and aldimines. Products included cyclic β-enamino esters 1aa-ac, very useful for the synthesis of natural products.

  开发了一种使用易得的起始原料制备β-烯胺酯1的通用方法。使锂化的烯胺与碳酸二乙酯或氯甲酸苄酯反应，形成β-烯氨基酯1a或1b。来自各种各样的酮亚胺和醛亚胺的反应相当普遍。产品包括环状β-烯胺酯1aa-ac，对合成天然产物非常有用。