(+)-(1R,4S)-1-(3-indolylmethyl)-4-iso-propyl-2,4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-dione | 374114-93-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: (+)-(1R,4S)-1-(3-indolylmethyl)-4-iso-propyl-2,4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-dione
• 英文别名: (1R,4S)-1-(1H-indol-3-ylmethyl)-4-propan-2-yl-2,4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-dione
• CAS: 374114-93-9
• 化学式: C₂₃H₂₂N₄O₂
• 分子量: 386.453
• InChiKey: APMCZPBBLORYEB-UXHICEINSA-N

物化性质

• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  77.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+)-(1R,4S)-1-(3-indolylmethyl)-4-iso-propyl-2,4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-dione 在 三氟乙酸 作用下， 反应 2.3h， 以48%的产率得到(+)-(5aR,8S,15bR,16aR)-8-iso-propyl-5,5a,8,15b,16,16a-hexahydro-indolo[3'',2''-4',5']pyrrolo[2',1'-3,4]pyrazino[2,1-b]quinazoline-7,10-dione
  参考文献：
  名称：

  Influence of N(2)-substitution in the alkylation of (4S)-alkyl-2,4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-diones

  摘要：

  1-Alkylation of O(3)-lactim, N(11)-azaenolate dilithium species derived from N(2)-H compounds 1a and 1b and the lithium azaenolates derived from the N(2)-phenyl and N(2)-(1-arylethyl) substituted compounds 2, 3 and 4 is studied. In 1 the trans-diastereoselectivity of 1-alkylation is controlled by 1,4-asyrnmetric induction, with some of these products prect.rsors of the ent-ardeemin framework. By contrast in compounds 2-4, the stabilization of the lithium azaenolate imposed by the phenyl substituent in 2, and the repulsive steric 1,2- interactions present in the initially formed 1,4-trans derivatives of 3 and 4, favou a C(1)-epimerization to the 1,4-cis isomers. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.07.034
• 作为产物：
  描述：

  D-色氨酸甲酯 在 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 32.0h， 生成 (+)-(1R,4S)-1-(3-indolylmethyl)-4-iso-propyl-2,4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-dione
  参考文献：
  名称：

  3-Arylmethylpiperazine-2,5-diones 的区域选择性 N-酰化：(-)-Glyantrypine 和 (-)-Fumiquinazoline F 的短合成

  摘要：

  衍生自相应哌嗪-2,5-二酮的 2,5-双-O-三甲基甲硅烷基-3,6-二氢吡嗪中 3-芳基甲基取代基的折叠构象屏蔽了 N(1) 位，允许在相邻位置进行单酰化氮原子。利用这种区域选择性，开发了以 d-色氨酸甲酯为起始原料的 (-)-glyantrypine 和 (-)-fumiquinazoline F 的四步全合成方法。

  DOI：

  10.1055/s-2001-16785

文献信息

• Regioselective N-Acylation of 3-Arylmethylpiperazine-2,5-diones: Short Synthesis of (-)-Glyantrypine and (-)-Fumiquinazoline F
  作者：Fernando Hernández、Astrid Lumetzberger、Carmen Avendaño、Mónica Söllhuber

  DOI：10.1055/s-2001-16785

  日期：——

  The folded conformation of the 3-arylmethyl substituent in 2,5-bis-O-trimethylsilyl-3,6-dihydropyrazines derived from the corresponding piperazine-2,5-diones, shields the N(1)-position allowing monoacylation at the neighbouring nitrogen atom. This regioselectivity was used to develop a four-step total synthesis of (-)-glyantrypine and (-)-fumiquinazoline F starting from d-tryptophan methyl ester.

  衍生自相应哌嗪-2,5-二酮的 2,5-双-O-三甲基甲硅烷基-3,6-二氢吡嗪中 3-芳基甲基取代基的折叠构象屏蔽了 N(1) 位，允许在相邻位置进行单酰化氮原子。利用这种区域选择性，开发了以 d-色氨酸甲酯为起始原料的 (-)-glyantrypine 和 (-)-fumiquinazoline F 的四步全合成方法。
• Influence of N(2)-substitution in the alkylation of (4S)-alkyl-2,4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-diones
  作者：Fernando Hernández、Viviana Morales、Félix L. Buenadicha、Mónica Söllhuber、Carmen Avendaño

  DOI：10.1016/j.tetasy.2004.07.034

  日期：2004.10

  1-Alkylation of O(3)-lactim, N(11)-azaenolate dilithium species derived from N(2)-H compounds 1a and 1b and the lithium azaenolates derived from the N(2)-phenyl and N(2)-(1-arylethyl) substituted compounds 2, 3 and 4 is studied. In 1 the trans-diastereoselectivity of 1-alkylation is controlled by 1,4-asyrnmetric induction, with some of these products prect.rsors of the ent-ardeemin framework. By contrast in compounds 2-4, the stabilization of the lithium azaenolate imposed by the phenyl substituent in 2, and the repulsive steric 1,2- interactions present in the initially formed 1,4-trans derivatives of 3 and 4, favou a C(1)-epimerization to the 1,4-cis isomers. (C) 2004 Elsevier Ltd. All rights reserved.