(3S,5'S)-6-bromo-5'-phenylspiro[1,2-dihydroindene-3,3'-morpholine]-2'-one | 220024-58-8

• 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: (3S,5'S)-6-bromo-5'-phenylspiro[1,2-dihydroindene-3,3'-morpholine]-2'-one
• CAS: 220024-58-8
• 化学式: C₁₈H₁₆BrNO₂
• 分子量: 358.235
• InChiKey: NOHDKFMKUJUBKY-AEFFLSMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,5'S)-6-bromo-5'-phenylspiro[1,2-dihydroindene-3,3'-morpholine]-2'-one 在 palladium diacetate 、 1,3-双(二苯基膦)丙烷 、 potassium carbonate 、 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 25.0~70.0 ℃ 、101.33 kPa 条件下， 反应 12.0h， 生成 (S)-1-((S)-2-Hydroxy-1-phenyl-ethylamino)-indan-1,5-dicarboxylic acid dimethyl ester
  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 以 甲苯 为溶剂， 反应 24.0h， 以52%的产率得到(3S,5'S)-6-bromo-5'-phenylspiro[1,2-dihydroindene-3,3'-morpholine]-2'-one
  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

文献信息

• Asymmetric Strecker-Type Reaction of α-Aryl Ketones. Synthesis of (<i>S</i>)-αM4CPG, (<i>S</i>)-MPPG, (<i>S</i>)-AIDA, and (<i>S</i>)-APICA, the Antagonists of Metabotropic Glutamate Receptors
  作者：Dawei Ma、Hongqi Tian、Guixiang Zou

  DOI：10.1021/jo981297a

  日期：1999.1.1

  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.