ethyl (1S,5'S)-2'-oxo-5'-phenylspiro[2,3-dihydroindene-1,3'-morpholine]-5-carboxylate | 220024-59-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: ethyl (1S,5'S)-2'-oxo-5'-phenylspiro[2,3-dihydroindene-1,3'-morpholine]-5-carboxylate
• CAS: 220024-59-9
• 化学式: C₂₁H₂₁NO₄
• 分子量: 351.402
• InChiKey: TZARCHGKBBWDIB-NQIIRXRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (1S,5'S)-2'-oxo-5'-phenylspiro[2,3-dihydroindene-1,3'-morpholine]-5-carboxylate 在 lead(IV) acetate 、 盐酸 、 potassium carbonate 、 methyloxirane 作用下， 反应 36.75h， 生成 (S)-1-aminoindan-1,5-dicarboxylic acid
  参考文献：
  名称：

  Asymmetric Strecker-Type Reaction of α-Aryl Ketones. Synthesis of (S)-αM4CPG, (S)-MPPG, (S)-AIDA, and (S)-APICA, the Antagonists of Metabotropic Glutamate Receptors

  摘要：

  Heating a mixture of alpha-aryl ketone with (R)-phenylglycinol produces a mixture of imine and 1,3-dioxazolidine. Treatment of this mixture with trimethylsilyl cyanide followed by transformation of nitrile to ester gives Strecker-type reaction products. The diastereoselectivity of the generated alpha-amino esters is from 2/1 to 7/1, and the (R,S)isomer is found as the major product. The (R,S) and (R,R)isomers can be separated by conversion to their N-Cbz or cyclization derivatives. Using this methodology, four antagonists of metabotropic glutamate receptors, (S)-alpha M4CPG, (S)-MPPG, (S)AIDA, and (S)-APICA, are synthesized.

  DOI：

  10.1021/jo981297a
• 作为产物：
  描述：

  methyl 5-bromo-1-[[(1R)-2-hydroxy-1-phenylethyl]amino]-2,3-dihydroindene-1-carboxylate 在 palladium diacetate 、 1,3-双(二苯基膦)丙烷 、 三乙胺 作用下， 以 二甲基亚砜 、 甲苯 为溶剂， 70.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 生成 ethyl (1S,5'S)-2'-oxo-5'-phenylspiro[2,3-dihydroindene-1,3'-morpholine]-5-carboxylate
  参考文献：
  名称：

  Asymmetric Strecker-Type Reaction of α-Aryl Ketones. Synthesis of (S)-αM4CPG, (S)-MPPG, (S)-AIDA, and (S)-APICA, the Antagonists of Metabotropic Glutamate Receptors

  摘要：

  Heating a mixture of alpha-aryl ketone with (R)-phenylglycinol produces a mixture of imine and 1,3-dioxazolidine. Treatment of this mixture with trimethylsilyl cyanide followed by transformation of nitrile to ester gives Strecker-type reaction products. The diastereoselectivity of the generated alpha-amino esters is from 2/1 to 7/1, and the (R,S)isomer is found as the major product. The (R,S) and (R,R)isomers can be separated by conversion to their N-Cbz or cyclization derivatives. Using this methodology, four antagonists of metabotropic glutamate receptors, (S)-alpha M4CPG, (S)-MPPG, (S)AIDA, and (S)-APICA, are synthesized.

  DOI：

  10.1021/jo981297a