tert-butyl (2R)-2-({(2E)-2-[(4-methoxyphenyl)imino]ethanoyl}oxy)propanoate | 476689-68-6

• 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-[(4-methoxyphenyl)imino]ethanoyl}oxy)propanoate
• CAS: 476689-68-6
• 化学式: C₁₆H₂₁NO₅
• 分子量: 307.346
• InChiKey: KTEAEBBBFPADHB-JDAJCMJVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.67
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  74.19
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (2R)-2-({(2E)-2-[(4-methoxyphenyl)imino]ethanoyl}oxy)propanoate 在 四氯化钛 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.83h， 生成 (3R,6R)-3-Allyl-4-(4-methoxy-phenyl)-6-methyl-morpholine-2,5-dione
  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 15.5h， 生成 tert-butyl (2R)-2-({(2E)-2-[(4-methoxyphenyl)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