(1S,6R)-1-((1(R)-phenylethyl)amino)-cis-3-azabicyclo[4.4.0]decan-2,4-dione | 799781-94-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: (1S,6R)-1-((1(R)-phenylethyl)amino)-cis-3-azabicyclo[4.4.0]decan-2,4-dione
• 英文别名: (4aR,8aS)-8a-[[(1R)-1-phenylethyl]amino]-4,4a,5,6,7,8-hexahydroisoquinoline-1,3-dione
• CAS: 799781-94-5
• 化学式: C₁₇H₂₂N₂O₂
• 分子量: 286.374
• InChiKey: VOIYBUAPHPDFFI-MRRJBJDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,6R)-1-((1(R)-phenylethyl)amino)-cis-3-azabicyclo[4.4.0]decan-2,4-dione 在 palladium on activated charcoal ammonium formate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以81%的产率得到(1S,6R)-1-amino-cis-3-azabicyclo[4.4.0]decan-2,4-dione
  参考文献：
  名称：

  Stereoselective synthesis of (1R,2S)- and (1S,2R)-1-amino-cis-3-azabicyclo[4.4.0]decan-2,4-dione hydrochlorides: bicyclic glutamic acid derivatives

  摘要：

  Asymmetric synthesis of (1R,2S)- and (1S,2R)-1-amino-cis-3-azabicyclo[4.4.0]decan-2,4-diones has been achieved. The underlying second generation asymmetric synthesis proceeds via a Strecker reaction with commercially available (R)-1-phenylethylamine (1-PEA) as chiral auxiliary, TMSCN as cyanide source and racemic ethyl 2-(2-oxocyclohex-1-yl)ethanoate. A ring closure addition-elimination reaction between an amide nitrogen and the ester functionality leads to the 1-amino-3-azabicyclo[4.4.0]decan-2,4-diones. The absolute configurations of the title compounds have been assigned based on detailed NMR-spectroscopic analysis and X-ray data. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2004.07.104
• 作为产物：
  描述：

  2-环己酮乙酸乙酯 在 甲醇 、 硫酸 、 silica gel 、 对甲苯磺酸 、 zinc(II) chloride 作用下， 以 二氯甲烷 、 环己烷 、 乙酸乙酯 、 苯 为溶剂， 反应 208.0h， 生成 (1S,6R)-1-((1(R)-phenylethyl)amino)-cis-3-azabicyclo[4.4.0]decan-2,4-dione
  参考文献：
  名称：

  Stereoselective synthesis of (1R,2S)- and (1S,2R)-1-amino-cis-3-azabicyclo[4.4.0]decan-2,4-dione hydrochlorides: bicyclic glutamic acid derivatives

  摘要：

  Asymmetric synthesis of (1R,2S)- and (1S,2R)-1-amino-cis-3-azabicyclo[4.4.0]decan-2,4-diones has been achieved. The underlying second generation asymmetric synthesis proceeds via a Strecker reaction with commercially available (R)-1-phenylethylamine (1-PEA) as chiral auxiliary, TMSCN as cyanide source and racemic ethyl 2-(2-oxocyclohex-1-yl)ethanoate. A ring closure addition-elimination reaction between an amide nitrogen and the ester functionality leads to the 1-amino-3-azabicyclo[4.4.0]decan-2,4-diones. The absolute configurations of the title compounds have been assigned based on detailed NMR-spectroscopic analysis and X-ray data. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2004.07.104

文献信息

• Stereoselective synthesis of (1R,2S)- and (1S,2R)-1-amino-cis-3-azabicyclo[4.4.0]decan-2,4-dione hydrochlorides: bicyclic glutamic acid derivatives
  作者：Philippe Bisel、Kamalesh P. Fondekar、Franz-Josef Volk、August W. Frahm

  DOI：10.1016/j.tet.2004.07.104

  日期：2004.11

  Asymmetric synthesis of (1R,2S)- and (1S,2R)-1-amino-cis-3-azabicyclo[4.4.0]decan-2,4-diones has been achieved. The underlying second generation asymmetric synthesis proceeds via a Strecker reaction with commercially available (R)-1-phenylethylamine (1-PEA) as chiral auxiliary, TMSCN as cyanide source and racemic ethyl 2-(2-oxocyclohex-1-yl)ethanoate. A ring closure addition-elimination reaction between an amide nitrogen and the ester functionality leads to the 1-amino-3-azabicyclo[4.4.0]decan-2,4-diones. The absolute configurations of the title compounds have been assigned based on detailed NMR-spectroscopic analysis and X-ray data. (C) 2004 Published by Elsevier Ltd.