(4S)-4-异丙基-1,2,3,4-四氢-5H-吡嗪并[2,1-b]喹唑啉-3,6-二酮 | 264236-54-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: (4S)-4-异丙基-1,2,3,4-四氢-5H-吡嗪并[2,1-b]喹唑啉-3,6-二酮
• 英文名称: (4S)-4-isopropyl-1,2,3,4-tetrahydro-5H-pyrazino[2,1-b]quinazoline-3,6-dione
• 英文别名: (4S)-4-isopropyl-2,4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-dione；(4S)-4-propan-2-yl-2,4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-dione
• CAS: 264236-54-6
• 化学式: C₁₄H₁₅N₃O₂
• 分子量: 257.292
• InChiKey: PMIGNQMVDXOAIF-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  61.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S)-4-异丙基-1,2,3,4-四氢-5H-吡嗪并[2,1-b]喹唑啉-3,6-二酮 在 sodium carbonate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 25.17h， 生成 (-)-(1S,4S)-3-ethoxy-4-isopropyl-1-methyl-1,4-dihydropyrazino[2,1-b]quinazolin-6-one
  参考文献：
  名称：

  A new stereocontrolled approach to fused polycyclic compounds containing a diketopiperazine ring

  摘要：

  Representative (1S)- and (4S)-alkyl-1,4-dihydropyrazino[2,1-b]quinazoline-3,6-dione lactim ethers were regio- and diastereoselectively alkylated after metallation to give the corresponding 1,4-trans-isomers with retention of the stereocentres. The results were compared with the previously studied lactams. The (1R,4S)-dialkyl derivatives obtained by C(1)-alkyation with bifunctional reagents were lately cyclized to complex polycyclic compounds through a second N(2)-alkylation promoted by sodium iodide. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.08.034
• 作为产物：
  描述：

  CBZ-L-缬氨酸 在 ammonium cerium(IV) nitrate 、 地昔帕明 、 三丁基膦 、 双(三甲基硅烷基)氨基钾 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， -78.0~20.0 ℃ 、241.32 kPa 条件下， 反应 73.17h， 生成 (4S)-4-异丙基-1,2,3,4-四氢-5H-吡嗪并[2,1-b]喹唑啉-3,6-二酮
  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

文献信息

• A New Route toward 4-Substituted Pyrazino[2,1-<i>b</i>]quinazoline-3,6-dione Systems. Total Synthesis of Glyantrypine
  作者：Pilar Cledera、Carmen Avendaño、J. Carlos Menéndez

  DOI：10.1021/jo991626e

  日期：2000.3.1

  Treatment of sodium N-(o-azidobenzoyl)aminoacylglycinates 8 with acetic anhydride afforded 1-acetyl-4-(o-azidobenzoyl)-2,5-piperazinediones 7, with complete retention of the stereochemistry. The intramolecular aza Wittig reactions of compounds 7 in the presence of tributylphosphine followed by deacetylation gave 1,2-unsubstituted pyrazino[2,1-b]quinazoline-3,6-diones 1. This route was adapted to the synthesis of both enantiomers of the alkaloid glyantrypine.
• 1-Alkyl-2,4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-diones as glycine templates. Synthesis of Fiscalin B
  作者：Fernando Hernández、Félix L. Buenadicha、Carmen Avendaño、Mónica Söllhuber

  DOI：10.1016/s0957-4166(02)00027-7

  日期：2002.1

  An excess of base allows the regio- and diastereoselective alkylation at C(4) of the glycine templates 1-methyl(isopropyl)-2,4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-diones 9a and 9b without the need for N(2)-protecting groups. While the alkylation of 9a gave exclusively the 1,4-anti-isomers, the isopropyl derivative 9b required much longer reaction times and occurred with lower diastereoselectivity. Fiscalin B 3 was obtained by alkylation of 9b with N-Boc-3-indolylmethyl bromide followed by indole deprotection. (C) 2002 Elsevier Science Ltd. All rights reserved.
• A new stereocontrolled approach to fused polycyclic compounds containing a diketopiperazine ring
  作者：Fernando Hernández、Carmen Avendaño、Mónica Söllhuber

  DOI：10.1016/j.tetasy.2005.08.034

  日期：2005.10

  Representative (1S)- and (4S)-alkyl-1,4-dihydropyrazino[2,1-b]quinazoline-3,6-dione lactim ethers were regio- and diastereoselectively alkylated after metallation to give the corresponding 1,4-trans-isomers with retention of the stereocentres. The results were compared with the previously studied lactams. The (1R,4S)-dialkyl derivatives obtained by C(1)-alkyation with bifunctional reagents were lately cyclized to complex polycyclic compounds through a second N(2)-alkylation promoted by sodium iodide. (c) 2005 Elsevier Ltd. All rights reserved.
• 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.