methyl (2R)-2-(4-methoxyanilino)pentanoate | 476689-73-3

• 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: methyl (2R)-2-(4-methoxyanilino)pentanoate
• CAS: 476689-73-3
• 化学式: C₁₃H₁₉NO₃
• 分子量: 237.299
• InChiKey: JNRUNIKXMJZPFK-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (2R)-2-(4-methoxyanilino)pentanoate 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.67h， 以45%的产率得到methyl (2R)-2-aminopentanoate
  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：

  tert-butyl (2R)-2-({(2E)-2-[(4-methoxyphenyl)imino]ethanoyl}oxy)propanoate 在 10percent Pd/C lithium hydroxide 、 氢气 、 Dimethylzinc 、 magnesium chloride 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 正己烷 、 二氯甲烷 、 水 为溶剂， -78.0~20.0 ℃ 、405.33 kPa 条件下， 反应 12.35h， 生成 methyl (2R)-2-(4-methoxyanilino)pentanoate
  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

• Novel Stereocontrolled Addition of Allylmetal Reagents to α-Imino Esters:  Efficient Synthesis of Chiral Tetrahydroquinoline Derivatives
  作者：Romano Di Fabio、Giuseppe Alvaro、Barbara Bertani、Daniele Donati、Simone Giacobbe、Carla Marchioro、Carlotta Palma、Sean M. Lynn

  DOI：10.1021/jo020327d

  日期：2002.10.1

  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.