N-(2,6-dichlorophenyl)-1,2,3,4-tetrahydroisoquinoline-1,3-dione | 126070-14-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: N-(2,6-dichlorophenyl)-1,2,3,4-tetrahydroisoquinoline-1,3-dione
• 英文别名: 2-(2,6-dichlorophenyl)-4H-isoquinoline-1,3-dione
• CAS: 126070-14-2
• 化学式: C₁₅H₉Cl₂NO₂
• 分子量: 306.148
• InChiKey: MRCAWQQIRQEGQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2,6-dichlorophenyl)-1,2,3,4-tetrahydroisoquinoline-1,3-dione 在 碳酸氢钠 作用下， 以 水 为溶剂， 生成 2-[2-[(2,6-dichlorophenyl)carbamoyl]phenyl]acetic acid
  参考文献：
  名称：

  Modena, T.; Azzolina, O.; Genta, I., Il Farmaco, 1989, vol. 44, # 7-8, p. 721 - 730

  摘要：

  DOI：
• 作为产物：
  描述：

  邻羧基苯乙酸 、 2,6-二氯苯胺 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以70%的产率得到N-(2,6-dichlorophenyl)-1,2,3,4-tetrahydroisoquinoline-1,3-dione
  参考文献：
  名称：

  Photochemical synthesis of benzoxazolo[3,2-b]isoquinolin-11-one and isoquinolino[3,2-b][1,3]benzoxazin-11-one under basic conditions

  摘要：

  Irradiation of N-phenyl substituted isoquinolines in acetonitrile containing 1 M NaOH in a multilamp reactor (MLR) furnished benzoxazolo[3,2-b]isoquinolin-11-ones. In contrast, irradiation of the N-benzyl substituted isoquinoline derivative under the same conditions afforded the hydrolysed N-benzylbenzamide derivative. The isoquinolinobenzoxazine was obtained by irradiating the N-benzyl substituted isoquinoline derivative at higher basic conditions. The required isoquinolines were synthesized under solvent-free, solid supported microwave conditions. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.02.068

文献信息

• Specific inhibitor of puromycin-sensitive aminopeptidase with a homophthalimide skeleton: identification of the target molecule and a structure–activity relationship study
  作者：Masato Komoda、Hiroki Kakuta、Hiroyasu Takahashi、Yasuyuki Fujimoto、Shizuo Kadoya、Fuminori Kato、Yuichi Hashimoto

  DOI：10.1016/s0968-0896(00)00231-5

  日期：2001.1

  ,3-dione (2: PIQ-22) was found to be a potent and specific inhibitor of puromycin-sensitive aminopeptidase (PSA). Lineweaver-Burk plot analysis showed that PSA is inhibited by PIQ-22 in a non-competitive manner. Structure -activity relationship studies indicated that tautomerism of the imidobenzoylketone group in the cyclic imide moiety of the PIQ-22 skeleton is important for the inhibitory activity

  发现2-（2，6-二乙基苯基）-1，2，3，4-四氢异喹啉-1，3-二酮（2：PIQ-22）是嘌呤霉素敏感性氨基肽酶（PSA）的有效和特异性抑制剂。Lineweaver-Burk图分析表明，PSA被PIQ-22抑制为非竞争性方式。结构-活性关系研究表明，PIQ-22骨架的环状酰亚胺部分中的亚氨基苯甲酰基酮基的互变异构对于抑制活性很重要。
• A new photochemical synthesis of benzoxazolo[3,2-b]isoquinolin-11-one and isoquinolino[3,2-b][1,3]benzoxazin-11-one
  作者：Annamalai Senthilvelan、Vayalakkavoor T. Ramakrishnan

  DOI：10.1016/s0040-4039(02)01955-x

  日期：2002.11

  Photocyclization of substituted tetrahydroisoquinoline-1,3-diones, under base-mediated conditions, afforded benzoxazolo[3,2-b]isoquinotin-11-ones and an isoquinolino[3,2-b]benzoxazin-11-one. (C) 2002 Elsevier Science Ltd. All rights reserved.
• MODENA, T.;AZZOLINA, O.;GENTA, I.;MAZZA, M., FARMACO, 44,(1989) N-8, C. 721-729
  作者：MODENA, T.、AZZOLINA, O.、GENTA, I.、MAZZA, M.

  DOI：——

  日期：——
• Modena, T.; Azzolina, O.; Genta, I., Il Farmaco, 1989, vol. 44, # 7-8, p. 721 - 730
  作者：Modena, T.、Azzolina, O.、Genta, I.、Mazza, M.

  DOI：——

  日期：——
• Photochemical synthesis of benzoxazolo[3,2-b]isoquinolin-11-one and isoquinolino[3,2-b][1,3]benzoxazin-11-one under basic conditions
  作者：A. Senthilvelan、D. Thirumalai、V.T. Ramakrishnan

  DOI：10.1016/j.tet.2005.02.068

  日期：2005.4

  Irradiation of N-phenyl substituted isoquinolines in acetonitrile containing 1 M NaOH in a multilamp reactor (MLR) furnished benzoxazolo[3,2-b]isoquinolin-11-ones. In contrast, irradiation of the N-benzyl substituted isoquinoline derivative under the same conditions afforded the hydrolysed N-benzylbenzamide derivative. The isoquinolinobenzoxazine was obtained by irradiating the N-benzyl substituted isoquinoline derivative at higher basic conditions. The required isoquinolines were synthesized under solvent-free, solid supported microwave conditions. (c) 2005 Elsevier Ltd. All rights reserved.