(3S)-4-(o-azidobenzoyl)-1-p-methoxybenzyl-3-isopropylpiperazine-2,5-dione | 799783-35-0

• 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)-4-(o-azidobenzoyl)-1-p-methoxybenzyl-3-isopropylpiperazine-2,5-dione
• CAS: 799783-35-0
• 化学式: C₂₂H₂₃N₅O₄
• 分子量: 421.456
• InChiKey: MOCNEPNHRSCHTQ-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.67
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  115.68
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (3S)-4-(o-azidobenzoyl)-1-p-methoxybenzyl-3-isopropylpiperazine-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 89.17h， 生成 (+)-(1R,4S)-1-p-fluorobenzyl-4-iso-propyl-2,4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-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：

  CBZ-L-缬氨酸 在 地昔帕明 、 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 、 甲苯 为溶剂， -78.0~20.0 ℃ 、241.32 kPa 条件下， 反应 56.17h， 生成 (3S)-4-(o-azidobenzoyl)-1-p-methoxybenzyl-3-isopropylpiperazine-2,5-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