2-[(Z)-methoxycarbonylmethylene]-4-oxo-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine

• 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: 2-[(Z)-methoxycarbonylmethylene]-4-oxo-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine
• 英文别名: methyl (Z)-2,3,4,5-tetrahydro-4-oxo-1H-1,5-benzodiazepin-2-ylideneacetate；2-methoxycarbonylmethylene-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-4-one；methyl (2Z)-2-(4-oxo-1,5-dihydro-1,5-benzodiazepin-2-ylidene)acetate
• 化学式: C₁₂H₁₂N₂O₃
• 分子量: 232.239
• InChiKey: DCPCAILLRHMNJO-FPLPWBNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[(Z)-methoxycarbonylmethylene]-4-oxo-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine 在 巯基乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以95%的产率得到2,3-dihydro-1-[(E)-3-methoxy-1-methyl-3-oxo-1-propenyl]-2-oxo-1H-1,3-benzimidazole
  参考文献：
  名称：

  One-pot microwave assisted synthesis of new 2-alkoxycarbonylmethylene-4-oxo-1,5-benzo-, naphtho-, and pyridodiazepines and assessment of their cytogenetic activity

  摘要：

  1,5-Benzo-, naphtho-, and pyridodiazepines 3 have been synthesized in excellent yields in one-step from the reaction of o-phenylenediamines with acetonedicarboxylates through microwave assisted acid catalysis. In order to ascertain their cytogenetic activity in vitro at doses equivalent to the per os doses of common 1,4-benzodiazepine drugs, Sister Chromatid Exchanges (SCEs) were employed, and for the determination of cytostaticity the Proliferation Rate Index (PRI) on lymphocytes of human whole blood cultures was estimated. It was found that benzodiazepines 3a, 3c, and 3e exhibit significant cytoprotection, but mild cytostatic effect (a statistically significant reduction of SCEs and a confined decrease of PRI values at similar concentrations). The most active compound was found to be 3e. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.06.028
• 作为产物：
  描述：

  1,3-丙酮二羧酸二甲酯 、 邻苯二胺 在 溶剂黄146 作用下， 以 水 为溶剂， 反应 0.05h， 以91%的产率得到2-[(Z)-methoxycarbonylmethylene]-4-oxo-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine
  参考文献：
  名称：

  One-pot microwave assisted synthesis of new 2-alkoxycarbonylmethylene-4-oxo-1,5-benzo-, naphtho-, and pyridodiazepines and assessment of their cytogenetic activity

  摘要：

  1,5-Benzo-, naphtho-, and pyridodiazepines 3 have been synthesized in excellent yields in one-step from the reaction of o-phenylenediamines with acetonedicarboxylates through microwave assisted acid catalysis. In order to ascertain their cytogenetic activity in vitro at doses equivalent to the per os doses of common 1,4-benzodiazepine drugs, Sister Chromatid Exchanges (SCEs) were employed, and for the determination of cytostaticity the Proliferation Rate Index (PRI) on lymphocytes of human whole blood cultures was estimated. It was found that benzodiazepines 3a, 3c, and 3e exhibit significant cytoprotection, but mild cytostatic effect (a statistically significant reduction of SCEs and a confined decrease of PRI values at similar concentrations). The most active compound was found to be 3e. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.06.028

文献信息

• A new route to 1H-1,5-benzodiazepinones
  作者：John Ackroyd、Feodor Scheinmann

  DOI：10.1039/c39810000339

  日期：——

  Dimethyl allene-1,3-dicarboxylates react with o-phenylenediamine to give 1H-1, 5-benzodiazepinones and not benzimidazoles; the transient enamine intermediate shows preference for a 7-exo-trig ring closure.

  1,3-二羧酸二甲酯与邻苯二胺反应生成1 H -1，5-苯并二氮杂pin酮而不是苯并咪唑; 瞬时烯胺中间体显示出对7 -exo-trig闭环的偏爱。
• Ackroyd, John; Scheinmann, Feodor, Journal of Chemical Research, Miniprint, 1982, # 4, p. 1012 - 1026
  作者：Ackroyd, John、Scheinmann, Feodor

  DOI：——

  日期：——
• Acheson, R. Morrin; Wallis, John D., Journal of the Chemical Society. Perkin transactions I, 1982, # 8, p. 1905 - 1914
  作者：Acheson, R. Morrin、Wallis, John D.

  DOI：——

  日期：——
• ACKROYD J.; SCHEINMANN F., J. CHEM. SOC. CHEM. COMMUN., 1981, NO 7, 339-340
  作者：ACKROYD J.、 SCHEINMANN F.

  DOI：——

  日期：——
• ACKROYD, J.;SCHEINMANN, F., J. CHEM. RES. MICROFICHE, 1982, N 4, 89
  作者：ACKROYD, J.、SCHEINMANN, F.

  DOI：——

  日期：——