tert-butyl-(2R)-2-({(2E)-2-[(5-chloro-2-iodophenyl)imino]ethanoyl}oxy)propanoate | 476689-66-4

• 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: tert-butyl-(2R)-2-({(2E)-2-[(5-chloro-2-iodophenyl)imino]ethanoyl}oxy)propanoate
• CAS: 476689-66-4
• 化学式: C₁₅H₁₇ClINO₄
• 分子量: 437.662
• InChiKey: XOOQUSAXFFOQMZ-SEYNJHBTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.92
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  64.96
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  tert-butyl-(2R)-2-({(2E)-2-[(5-chloro-2-iodophenyl)imino]ethanoyl}oxy)propanoate 在 四氯化钛 、 臭氧 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 5.58h， 生成 (1R)-2-tert-butoxy-1-methyl-2-oxoethyl (2R,4Z)-2-(5-chloro-2-iodoanilino)-4-(2-oxo-1-phenyl-3-pyrrolidinylidene)butanoate
  参考文献：
  名称：

  Novel Stereocontrolled Addition of Allylmetal Reagents to α-Imino Esters:  Efficient Synthesis of Chiral Tetrahydroquinoline Derivatives

  摘要：

  To prepare in multigram scale new antagonists of the glycine binding site associated to the NMDA receptor, an efficient distereoselective route was set up. The addition of suitable allyltin reagents to chiral N-aryl alpha-imino esters (R-(+)-tert-butyl lactate used as chiral auxiliary), gave the corresponding a amino acid-type derivative in high chemical yield and optical purity. This allylation reaction represents a novel example of efficient long-range stereodifferentiation process. In the last part of the synthesis, a regioselective Heck-type cyclization reaction enabled preparation of the target tetrasubstituted exocycle and trisubtituted endocycle double bond derivatives.

  DOI：

  10.1021/jo020327d
• 作为产物：
  描述：

  (+)-叔丁基 D-乳酸盐 在 4-二甲氨基吡啶 、 sodium periodate 、 四氧化锇 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 17.0h， 生成 tert-butyl-(2R)-2-({(2E)-2-[(5-chloro-2-iodophenyl)imino]ethanoyl}oxy)propanoate
  参考文献：
  名称：

  Novel Stereocontrolled Addition of Allylmetal Reagents to α-Imino Esters:  Efficient Synthesis of Chiral Tetrahydroquinoline Derivatives

  摘要：

  To prepare in multigram scale new antagonists of the glycine binding site associated to the NMDA receptor, an efficient distereoselective route was set up. The addition of suitable allyltin reagents to chiral N-aryl alpha-imino esters (R-(+)-tert-butyl lactate used as chiral auxiliary), gave the corresponding a amino acid-type derivative in high chemical yield and optical purity. This allylation reaction represents a novel example of efficient long-range stereodifferentiation process. In the last part of the synthesis, a regioselective Heck-type cyclization reaction enabled preparation of the target tetrasubstituted exocycle and trisubtituted endocycle double bond derivatives.

  DOI：

  10.1021/jo020327d

文献信息

• Chiral tetrahydroquinoline derivatives as potent anti-hyperalgesic agents in animal models of sustained inflammation and chronic neuropathic pain
  作者：Romano Di Fabio、Giuseppe Alvaro、Barbara Bertani、Daniele Donati、Domenica Maria Pizzi、Gabriella Gentile、Giorgio Pentassuglia、Simone Giacobbe、Simone Spada、Emiliangelo Ratti、Mauro Corsi、Mauro Quartaroli、Robert J. Barnaby、Giovanni Vitulli

  DOI：10.1016/j.bmcl.2006.12.022

  日期：2007.3

  Chiral tetrahydroquinoline derivatives have been prepared by an asymmetric Mannich-type condensation reaction using commercially available vinyloxyethylsilane and a N-arylimino R-(+)-t-butyl lactate ester, in the presence of a catalytic amount of metal triflates as Lewis acids. This synthetic approach gave rise to the target aldehyde intermediate in moderate facial diastereoselectivity and in high chemical yield. This efficient route enabled to scale up the synthesis of an orally bioavailable glycine antagonist showing outstanding in vivo anti-hyperalgesic activity in different animal models of sustained inflammation and chronic neuropathic pain. (c) 2006 Elsevier Ltd. All rights reserved.