(3S)-1-(o-azidobenzoyl)-4-p-methoxybenzyl-3-methylpiperazine-2,5-dione | 437768-86-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3S)-1-(o-azidobenzoyl)-4-p-methoxybenzyl-3-methylpiperazine-2,5-dione
• 英文别名: (3S)-1-(2-azidobenzoyl)-4-[(4-methoxyphenyl)methyl]-3-methylpiperazine-2,5-dione
• CAS: 437768-86-0
• 化学式: C₂₀H₁₉N₅O₄
• 分子量: 393.402
• InChiKey: RMFBRECANLPXHM-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  81.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3S)-1-(o-azidobenzoyl)-4-p-methoxybenzyl-3-methylpiperazine-2,5-dione 在 ammonium cerium(IV) nitrate 、 三丁基膦 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 水 、 甲苯 、 乙腈 为溶剂， 反应 33.33h， 生成 (1S,4R)-4-allyl-1-methyl-2,4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-dione
  参考文献：
  名称：

  1-Alkyl-2,4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-diones as glycine templates. Synthesis of Fiscalin B

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(02)00027-7
• 作为产物：
  描述：

  ethyl (S)-2-{[(4-methoxyphenyl)methyl]amino}propanoate 在 地昔帕明 、 双(三甲基硅烷基)氨基钾 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， -78.0~20.0 ℃ 、241.32 kPa 条件下， 反应 52.25h， 生成 (3S)-1-(o-azidobenzoyl)-4-p-methoxybenzyl-3-methylpiperazine-2,5-dione
  参考文献：
  名称：

  1-Alkyl-2,4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-diones as glycine templates. Synthesis of Fiscalin B

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(02)00027-7

文献信息

• 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.