6,7-dimethoxy-1-(5-methyl-2-nitrophenyl)-3,4-dihydroisoquinoline | 392726-84-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢异喹啉
• 英文名称: 6,7-dimethoxy-1-(5-methyl-2-nitrophenyl)-3,4-dihydroisoquinoline
• CAS: 392726-84-0
• 化学式: C₁₈H₁₈N₂O₄
• 分子量: 326.352
• InChiKey: UYDHZBLYNXSTCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  76.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6,7-dimethoxy-1-(5-methyl-2-nitrophenyl)-3,4-dihydroisoquinoline 在 sodium tetrahydroborate 、 tin(ll) chloride 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 32.0h， 生成 6,7-dimethoxy-1-(5-methyl-2-aminophenyl)-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Synthesis and antitumor activity of cis-dichloroplatinum(II) complexes of 1-(2-aminophenyl)-1,2,3,4-tetrahydroisoquinolines

  摘要：

  Fifteen cis-dichloroplatinum complexes (5a-5o) were synthesized by treatment of 1-(2-aminophenyl)-1,2,3,4-THIQs (4a-4o) with K2PtCl4. The antitumor activity of these compounds was examined against four different human tumor cell lines. Their structure-activity relationships for antitumor activity are reported. All of these compounds exhibited activity against MCF-7 cell line and showed good activity against WiDr cell line except 5c and 5f On the other hand, compounds 5j and 5o are more active than the other compounds against Hepa59T/VGH cell line. The electron-donating group at the 6-position of isoquinoline ring seems to decrease the antitumor activity and the chloro substituent at the C-4 position of the aniline ring shown the highest potency. The "trans influence" dominates the control of the stability of [1-(2-aminophenyl)1,2,3,4-THIQ]dichloroplatinums(II). (c) 2006 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.03.011
• 作为产物：
  描述：

  5-甲基-2-硝基苯甲酸 在 吡啶 、 氯化亚砜 、 三氯氧磷 作用下， 以 乙腈 、 苯 为溶剂， 反应 12.0h， 生成 6,7-dimethoxy-1-(5-methyl-2-nitrophenyl)-3,4-dihydroisoquinoline
  参考文献：
  名称：

  Synthesis and antitumor activity of cis-dichloroplatinum(II) complexes of 1-(2-aminophenyl)-1,2,3,4-tetrahydroisoquinolines

  摘要：

  Fifteen cis-dichloroplatinum complexes (5a-5o) were synthesized by treatment of 1-(2-aminophenyl)-1,2,3,4-THIQs (4a-4o) with K2PtCl4. The antitumor activity of these compounds was examined against four different human tumor cell lines. Their structure-activity relationships for antitumor activity are reported. All of these compounds exhibited activity against MCF-7 cell line and showed good activity against WiDr cell line except 5c and 5f On the other hand, compounds 5j and 5o are more active than the other compounds against Hepa59T/VGH cell line. The electron-donating group at the 6-position of isoquinoline ring seems to decrease the antitumor activity and the chloro substituent at the C-4 position of the aniline ring shown the highest potency. The "trans influence" dominates the control of the stability of [1-(2-aminophenyl)1,2,3,4-THIQ]dichloroplatinums(II). (c) 2006 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.03.011

文献信息

• An efficient and convenient synthesis of heterocycle-fused indazoles via the N–N bond forming reaction of nitroarenes induced by low-valent titanium reagent
  作者：Wei Lin、Ming-Hua Hu、Xian Feng、Cheng-Pao Cao、Zhi-Bin Huang、Da-Qing Shi

  DOI：10.1016/j.tet.2013.05.074

  日期：2013.8

  A mild and efficient one-pot protocol for the preparation of 8,13-dihydro-7H-indolo[2′,3′:3,4]pyrido[1,2-b]indazole and 5,6-dihydroindazolo[3,2-a]isoquinoline via the reductive cyclization of nitro-aryl substrates mediated by a low-valent titanium reagent has been developed. The attractive features of the current method include an N–N bond formation and the selective reduction of the CN bond and nitro

  一种温和有效的一锅法制备8,13-dihydro-7 H-吲哚并[2'，3'：3,4]吡啶并[1,2- b ]吲唑和5,6-二氢吲唑[3]已经开发了通过低价钛试剂介导的硝基-芳基底物的还原环化形成的2-2- α ]异喹啉。当前方法的吸引人的特征包括N–N键的形成以及C N键和硝基的选择性还原，通过控制反应混合物的pH值，一锅即可轻松实现。
• Unprecedented SnCl₂-Mediated Cyclization of Nitro Arenes via N−N Bond Formation
  作者：Devesh Sawant、Rishi Kumar、Prakas R. Maulik、Bijoy Kundu

  DOI：10.1021/ol053033y

  日期：2006.4.1

  A mild, efficient, one-pot protocol for the cyclization of nitro-aryl substrates using SnCl2 has been described. The mechanistic course of the reaction suggests the involvement of a hydroxylamine intermediate leading to an intramolecular cyclization via N-N bond formation. The versatility of the methodology has been demonstrated by using two nitro-aryl substrates derived from dihydroisoquinolines and dihydro-beta-carbolines. The intramolecular cyclization led to the formation of indazoles in high yields and purities.
• Synthesis and antitumor activity of cis-dichloroplatinum(II) complexes of 1-(2-aminophenyl)-1,2,3,4-tetrahydroisoquinolines
  作者：Chen-Yuan Kuo、Ming-Jung Wu、Yao-Haur Kuo

  DOI：10.1016/j.ejmech.2006.03.011

  日期：2006.8

  Fifteen cis-dichloroplatinum complexes (5a-5o) were synthesized by treatment of 1-(2-aminophenyl)-1,2,3,4-THIQs (4a-4o) with K2PtCl4. The antitumor activity of these compounds was examined against four different human tumor cell lines. Their structure-activity relationships for antitumor activity are reported. All of these compounds exhibited activity against MCF-7 cell line and showed good activity against WiDr cell line except 5c and 5f On the other hand, compounds 5j and 5o are more active than the other compounds against Hepa59T/VGH cell line. The electron-donating group at the 6-position of isoquinoline ring seems to decrease the antitumor activity and the chloro substituent at the C-4 position of the aniline ring shown the highest potency. The "trans influence" dominates the control of the stability of [1-(2-aminophenyl)1,2,3,4-THIQ]dichloroplatinums(II). (c) 2006 Elsevier SAS. All rights reserved.