(S)-benzyl 2-(6-oxo-6,7-dihydro-5H-benzo[f]pyrrolo[1,2-d][1,4]diazepin-5-yl)acetate | 147528-08-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 英文名称: (S)-benzyl 2-(6-oxo-6,7-dihydro-5H-benzo[f]pyrrolo[1,2-d][1,4]diazepin-5-yl)acetate
• 英文别名: 5H-Pyrrolo(1,2-d)(1,4)benzodiazepine-5-acetic acid, 6,7-dihydro-6-oxo-, phenylmethyl ester, (S)-；benzyl 2-[(5S)-6-oxo-5,7-dihydropyrrolo[1,2-d][1,4]benzodiazepin-5-yl]acetate
• CAS: 147528-08-3
• 化学式: C₂₁H₁₈N₂O₃
• 分子量: 346.386
• InChiKey: LONANILIWKPVLT-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  60.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (RS)-benzyl 2-(5-(but-3-en-1-yl)-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl)acetate 在 臭氧 、 二甲基硫 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 30.0h， 以77%的产率得到(S)-benzyl 2-(6-oxo-6,7-dihydro-5H-benzo[f]pyrrolo[1,2-d][1,4]diazepin-5-yl)acetate
  参考文献：
  名称：

  γ-Turn Mimicry with Benzodiazepinones and Pyrrolobenzodiazepinones Synthesized from a Common Amino Ketone Intermediate

  摘要：

  To investigate diazepinone analogues as gamma-turn mimics, seven 1,4-benzodiazepin-2-ones 6 and fourteen pyrrolo[1,2-d][1,4]benzodiazepin-6-ones 4 and 5 were synthesized from 1-(2-aminophenyl)pent-4-en-1-one (7). Acylation of aniline 7 with N-Boc-amino acids, olefin oxidation, Boc removal, and intramolecular Paal-Knorr condensation gave 4 and 5. Alternatively, Boc removal prior to oxidation gave benzodiazepinones 6, which were converted to 4 by ozonolysis and cyclization. Comparison of dihedral angle values for the amino acid component from X-ray analyses of 4g, 5f, and 61 and related diazepinones has catalogued the manner by which ring substituents affect the component's ability to mimic the central residues of gamma-turns.

  DOI：

  10.1021/acs.orglett.5b01679

文献信息

• γ-Turn Mimicry with Benzodiazepinones and Pyrrolobenzodiazepinones Synthesized from a Common Amino Ketone Intermediate
  作者：Aurélie A. Dörr、William D. Lubell

  DOI：10.1021/acs.orglett.5b01679

  日期：2015.7.17

  To investigate diazepinone analogues as gamma-turn mimics, seven 1,4-benzodiazepin-2-ones 6 and fourteen pyrrolo[1,2-d][1,4]benzodiazepin-6-ones 4 and 5 were synthesized from 1-(2-aminophenyl)pent-4-en-1-one (7). Acylation of aniline 7 with N-Boc-amino acids, olefin oxidation, Boc removal, and intramolecular Paal-Knorr condensation gave 4 and 5. Alternatively, Boc removal prior to oxidation gave benzodiazepinones 6, which were converted to 4 by ozonolysis and cyclization. Comparison of dihedral angle values for the amino acid component from X-ray analyses of 4g, 5f, and 61 and related diazepinones has catalogued the manner by which ring substituents affect the component's ability to mimic the central residues of gamma-turns.