N-烯丙基-N-苄基苯丙氨酸甲酯 | 183155-30-8

• 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
• 中文名称: N-烯丙基-N-苄基苯丙氨酸甲酯
• 英文名称: N-allyl-N-benzylphenylalanine methyl ester
• 英文别名: methyl (2S)-2-[benzyl(prop-2-enyl)amino]-3-phenylpropanoate
• CAS: 183155-30-8
• 化学式: C₂₀H₂₃NO₂
• 分子量: 309.408
• InChiKey: UTBKMXBRDZNALD-IBGZPJMESA-N

物化性质

• 沸点：
  419.0±45.0 °C(Predicted)
• 密度：
  1.073±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  N-烯丙基-N-苄基苯丙氨酸甲酯 在 titanium(IV) isopropylate 、 异丙基氯化镁 、 碳酸氢钠 作用下， 生成 2,3-dibenzyl-3-azabicyclo[3.1.0]hexan-1-ol
  参考文献：
  名称：

  Efficient and Practical Method for Synthesizing N-Heterocyclic Compounds Using Intramolecular Nucleophilic Acyl Substitution Reactions Mediated by Ti(O-i-Pr)₄/2i-PrMgX Reagent. Synthesis of Quinolones, Pyrroles, Indoles, and Optically Active N-Heterocycles Including Allopumiliotoxin Alkaloid 267A

  摘要：

  Treatment of N-(2- or 3-alkynyl)amino esters with a low-valent titanium reagent diisopropoxy(eta(2)-propene)titanium (1), generated in situ by the reaction of Ti(O-i-Pr)(4) and 2i-PrMgCl, resulted in an intramolecular nucleophilic acyl substitution (INAS) reaction to afford alpha-alkylidene-pyrrolidinones or -piperidinones. Thus, treatment of N-propargyl-anthranilates 5, -indole-2-carboxylates 10, or -pyrrole-2-carboxylates 13 with 1 gave 4-quinolones 7, [1,2-a]indoles, or [1,2-a]pyrroles, respectively. Similarly, N-alkynylated alpha- or beta-amino esters 14 or 15 with 1 afforded N-heterocycles 18 or 19. In the reaction of N-(2- or 3-alkenyl)amino esters with 1, the resulting INAS product underwent intramolecular carbonyl addition (ICA) reaction to afford the N-heterocyclic compounds having a cyclopropanol moiety in good to excellent yields. Thus, the treatment of N-alkenyl-anthranilate 4a, -indole-2-carboxylates 8 and 9, or -pyrrole-2-carboxylates 11 and 12 with 1 gave the corresponding quinoline derivative 6a, [1,2-a]indoles, or [1,2-a]pyrroles, respectively. The optically active N-heterocyclic compounds 20 and 21 were obtained from N-alkenylated alpha- or beta-amino esters 16 or 17. A highly efficient total synthesis of allopumiliotoxin alkaloid 267A has also been accomplished. Thus, the N-propargyl-2[(1-hydroxy-1-methoxycarbonyl)ethyl]pyrrolidine 24 (from L-proline in six steps) reacted with 1 to afford the corresponding indolidinone 25 in 67% yield, which has previously been converted to allopumiliotoxin 267A.

  DOI：

  10.1021/ja970810j
• 作为产物：
  描述：

  L-苯丙氨酸甲酯 在 三乙酰氧基硼氢化钠 、 碳酸氢钠 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 N-烯丙基-N-苄基苯丙氨酸甲酯
  参考文献：
  名称：

  Synthesis of Bicyclic Cyclopropylamines by Intramolecular Cyclopropanation of N-Allylamino Acid Dimethylamides

  摘要：

  [GRAPHICS]Cyclopropylamines and substituted cyclopropylamines are important building blocks or substituents in a variety of biologically active compounds, Here, we report the facile syntheses of cyclopropylamines by Ti(ll) mediated intramolecular coupling of a terminal olefinic moiety and the N,N dimethylcarboxamide moiety of amino acid derivatives. The products have novel and strained bicyclic structures. The yields were good (78-83%) for all three substrates with diastereomeric ratios of about 3:1.

  DOI：

  10.1021/ol9910520

文献信息

• Synthesis of Bicyclic Cyclopropyl- amines from Amino Acid Derivatives
  作者：Madeleine M. Joullié、Catherine A. Faler、Bin Cao

  DOI：10.3987/com-05-s(t)52

  日期：——

  The synthesis of novel |3.1.0| bicyclic cyclopropylamines from differently substituted amino acids using Ti(II)-mediated coupling and the extension of this methodology to provide |4.1.0| systems is described.

  小说合成|3.1.0| 使用 Ti(II) 介导的偶联和该方法的扩展以提供 |4.1.0| 来自不同取代的氨基酸的双环环丙​​胺 系统进行了描述。
• Efficient and Practical Method for Synthesizing N-Heterocyclic Compounds Using Intramolecular Nucleophilic Acyl Substitution Reactions Mediated by Ti(O-<i>i</i>-Pr)₄/2<i>i</i>-PrMgX Reagent. Synthesis of Quinolones, Pyrroles, Indoles, and Optically Active N-Heterocycles Including Allopumiliotoxin Alkaloid 267A
  作者：Sentaro Okamoto、Masayuki Iwakubo、Katsushige Kobayashi、Fumie Sato

  DOI：10.1021/ja970810j

  日期：1997.7.1

  Treatment of N-(2- or 3-alkynyl)amino esters with a low-valent titanium reagent diisopropoxy(eta(2)-propene)titanium (1), generated in situ by the reaction of Ti(O-i-Pr)(4) and 2i-PrMgCl, resulted in an intramolecular nucleophilic acyl substitution (INAS) reaction to afford alpha-alkylidene-pyrrolidinones or -piperidinones. Thus, treatment of N-propargyl-anthranilates 5, -indole-2-carboxylates 10, or -pyrrole-2-carboxylates 13 with 1 gave 4-quinolones 7, [1,2-a]indoles, or [1,2-a]pyrroles, respectively. Similarly, N-alkynylated alpha- or beta-amino esters 14 or 15 with 1 afforded N-heterocycles 18 or 19. In the reaction of N-(2- or 3-alkenyl)amino esters with 1, the resulting INAS product underwent intramolecular carbonyl addition (ICA) reaction to afford the N-heterocyclic compounds having a cyclopropanol moiety in good to excellent yields. Thus, the treatment of N-alkenyl-anthranilate 4a, -indole-2-carboxylates 8 and 9, or -pyrrole-2-carboxylates 11 and 12 with 1 gave the corresponding quinoline derivative 6a, [1,2-a]indoles, or [1,2-a]pyrroles, respectively. The optically active N-heterocyclic compounds 20 and 21 were obtained from N-alkenylated alpha- or beta-amino esters 16 or 17. A highly efficient total synthesis of allopumiliotoxin alkaloid 267A has also been accomplished. Thus, the N-propargyl-2[(1-hydroxy-1-methoxycarbonyl)ethyl]pyrrolidine 24 (from L-proline in six steps) reacted with 1 to afford the corresponding indolidinone 25 in 67% yield, which has previously been converted to allopumiliotoxin 267A.
• Synthesis of Bicyclic Cyclopropylamines by Intramolecular Cyclopropanation of <i>N</i>-Allylamino Acid Dimethylamides
  作者：Bin Cao、Dong Xiao、Madeleine M. Joullié

  DOI：10.1021/ol9910520

  日期：1999.12.1

  [GRAPHICS]Cyclopropylamines and substituted cyclopropylamines are important building blocks or substituents in a variety of biologically active compounds, Here, we report the facile syntheses of cyclopropylamines by Ti(ll) mediated intramolecular coupling of a terminal olefinic moiety and the N,N dimethylcarboxamide moiety of amino acid derivatives. The products have novel and strained bicyclic structures. The yields were good (78-83%) for all three substrates with diastereomeric ratios of about 3:1.
• Substituted azabicyclo[3.1.0]hexan-1-ols from aspartic and glutamic acid derivatives via titanium-mediated cyclopropanation
  作者：Catherine A. Faler、Madeleine M. Joullié

  DOI：10.1016/j.tetlet.2008.08.114

  日期：2008.11

  The Kulinkovich cyclopropanation reaction has been used to synthesize azabicyclo[3.1.0]hexanols from amino acid derivatives containing two ester moieties. (C) 2008 Elsevier Ltd. All rights reserved.