methyl (Z)-3-(benzylamino)-2-pentenoate | 1271792-95-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl (Z)-3-(benzylamino)-2-pentenoate
• 英文别名: (Z)-methyl 3-(benzylamino)pent-2-enoate；methyl (Z)-3-(benzylamino)pent-2-enoate
• CAS: 1271792-95-0
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: JBFNVRJQZHFTRZ-XFXZXTDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  methyl (Z)-3-(benzylamino)-2-pentenoate 、 2-氟-5-硝基苯甲酰氯 在 三乙胺 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 3.0h， 以86%的产率得到2-benzyl-3-ethyl-4-methoxycarbonyl-7-nitroisoquinolin-1(2H)-one
  参考文献：
  名称：

  Isoquinolin-1(2H)-ones and 1,6-naphthyridin-5(6H)-ones by an N-acylation-SNAr sequence

  摘要：

  A new synthesis of 2,3-dialkyl-4-carbomethoxyisoquinolin-1(2H)-ones and 6,7-dialky1-8-carbomethoxy1,6-naphthyridin-5(6H)-ones is reported. The process involves treatment of a beta-enaminoester with 2-fluoro-5-nitrobenzoyl chloride, 2-fluorobenzoyl chloride or 2-chloronicotinoyl chloride followed by heating in the presence of base. The conversion, which proceeds by an N-acylation-SNAr reaction sequence, affords 50-86% yields when R-1 is n-alkyl but <= 30% yields when R-1 is alpha-branched. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.12.033
• 作为产物：
  描述：

  3-氧代戊酸甲酯 、 苄胺 以 苯 为溶剂， 以80%的产率得到methyl (Z)-3-(benzylamino)-2-pentenoate
  参考文献：
  名称：

  三氯硅烷介导的β-氨基酯的立体选择性合成及其转化为高度对映体富集的β-内酰胺†

  摘要：

  已经开发出高度立体选择性的三氯硅烷介导的N-苄基烯胺的还原；低成本，易于制造的不含金属的催化剂与廉价的手性助剂的结合，通常可以完全控制立体选择性，从而在具有不同结构特征的底物上进行反应。通过容易的氢解脱保护，然后将β-氨基酯转化为2-氮杂环丁酮，对映体纯的β-内酰胺（> 98％ee）成功地完成了合成。

  DOI：

  10.1039/c0ob00570c

文献信息

• Triclorosilane-mediated stereoselective synthesis of β-amino esters and their conversion to highly enantiomerically enriched β-lactams
  作者：Stefania Guizzetti、Maurizio Benaglia、Martina Bonsignore、Laura Raimondi

  DOI：10.1039/c0ob00570c

  日期：——

  A highly stereoselective trichlorosilane-mediated reduction of N-benzyl enamines was developed; the combination of a low cost, easy to make metal-free catalyst and an inexpensive chiral auxiliary allowed to perform the reaction on substrates with different structural features often with total control of the stereoselectivity. By easy deprotection through hydrogenolysis followed by conversion of β-aminoester

  已经开发出高度立体选择性的三氯硅烷介导的N-苄基烯胺的还原；低成本，易于制造的不含金属的催化剂与廉价的手性助剂的结合，通常可以完全控制立体选择性，从而在具有不同结构特征的底物上进行反应。通过容易的氢解脱保护，然后将β-氨基酯转化为2-氮杂环丁酮，对映体纯的β-内酰胺（> 98％ee）成功地完成了合成。
• [EN] N-BENZYLINDOLE-3-ACETIC ACID DERIVATIVES FOR USE IN THE TREATMENT OF DRUG RESISTAN CANCER<br/>[FR] DERIVES D'ACIDE ACETIQUE N-BENZYLINDOLE-3 POUVANT ETRE UTILISES DANS LE TRAITEMENT DE CANCERS PHARMACORESISTANTS
  申请人：UNIV DUBLIN CITY

  公开号：WO2002020478A1

  公开（公告）日：2002-03-14

  A family of compounds, N-Benzylindoel-3-acetic acid derivatives, are active as inhibitors of multiple drug resistance protein (MRP) while having low direct toxicity, low COX -1 inhibitory activity and, in some cases, having useful activities such as COX-1 inhibition. The agents are useful in combination with MRP substrate drugs in the treatment of, for example, drug resistant cancer or tumours likely to develop drug resistant cancers because they can be given at higher concentration while being less toxic and having less side effects than known MRP inhibitors. The agents may also be more beneficial in the treatment of diseases which are dependent on MRP-1 activity or where MRP-1 activity reduces the effectiveness of existing therapies.
• Isoquinolin-1(2H)-ones and 1,6-naphthyridin-5(6H)-ones by an N-acylation-SNAr sequence
  作者：Richard A. Bunce、Baskar Nammalwar、Krishna Kumar Gnanasekaran、Nicholas R. Cain

  DOI：10.1016/j.tet.2013.12.033

  日期：2014.1

  A new synthesis of 2,3-dialkyl-4-carbomethoxyisoquinolin-1(2H)-ones and 6,7-dialky1-8-carbomethoxy1,6-naphthyridin-5(6H)-ones is reported. The process involves treatment of a beta-enaminoester with 2-fluoro-5-nitrobenzoyl chloride, 2-fluorobenzoyl chloride or 2-chloronicotinoyl chloride followed by heating in the presence of base. The conversion, which proceeds by an N-acylation-SNAr reaction sequence, affords 50-86% yields when R-1 is n-alkyl but <= 30% yields when R-1 is alpha-branched. (C) 2013 Elsevier Ltd. All rights reserved.