1-(5-氯-2-硝基苯基)-3,4-二氢-6,7-二甲氧基异喹啉 | 62206-13-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢异喹啉
• 中文名称: 1-(5-氯-2-硝基苯基)-3,4-二氢-6,7-二甲氧基异喹啉
• 英文名称: 1-(5-chloro-2-nitrophenyl)-6,7-dimethoxy-3,4-dihydroisoquinoline
• CAS: 62206-13-7
• 化学式: C₁₇H₁₅ClN₂O₄
• 分子量: 346.77
• InChiKey: UCWAPLAIZMBGPF-UHFFFAOYSA-N

物化性质

• 熔点：
  169 °C
• 沸点：
  494.3±45.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.235
• 拓扑面积：
  76.6
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 危险品标志：
  Xi

反应信息

• 作为反应物：
  描述：

  1-(5-氯-2-硝基苯基)-3,4-二氢-6,7-二甲氧基异喹啉 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 6,7-二甲氧基-1-(5-氯-2-氨基苯基)-1,2,3,4-四氢异喹啉
  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-氯-2-硝基苯甲酸 在 吡啶 、 草酰氯 、 三氯氧磷 作用下， 以 乙腈 、 苯 为溶剂， 反应 2.0h， 生成 1-(5-氯-2-硝基苯基)-3,4-二氢-6,7-二甲氧基异喹啉
  参考文献：
  名称：

  以二水氯化锡(II)为还原剂合成5,6-二氢吲唑并[3,2-a]异喹啉及其相关化合物

  摘要：

  在氯化锡 (II) 二水合物 (SnCl 2 .2H 2 O) 存在下，一系列 1-(2-硝基苯基)-3,4-二氢异喹啉在非常温和的反应条件下被还原，得到 5,6-二氢吲唑[3 ,2-a] 异喹啉 4a-h。提出了该反应的机理。

  DOI：

  10.1002/jccs.200500135

文献信息

• A Novel Synthesis of 5,6-Dihydroindazolo[3,2-<i>a</i> ]isoquinolines and Their Relative Compounds via Tin(II) Chloride Dihydrate as Reducing Agent
  作者：Chen-Yuan Kuo、Ming-Jung Wu

  DOI：10.1002/jccs.200500135

  日期：2005.10

  A series of 1-(2-nitrophenyl)-3,4-dihydroisoquinolines were reduced under very mild reaction conditions in the presence of Tin(II) chloride dihydrate (SnCl 2 .2H 2 O) to give 5,6-dihydroindazolo[3,2-a]isoquinolines 4a-h. A mechanism for this reaction is proposed.

  在氯化锡 (II) 二水合物 (SnCl 2 .2H 2 O) 存在下，一系列 1-(2-硝基苯基)-3,4-二氢异喹啉在非常温和的反应条件下被还原，得到 5,6-二氢吲唑[3 ,2-a] 异喹啉 4a-h。提出了该反应的机理。
• 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。
• Synthesis of indazole-N-oxides via the 1,7-electrocyclization of azomethine ylides
  作者：Miklós Nyerges、Andrea Virányi、Weimin Zhang、Paul W. Groundwater、Gábor Blaskó、László Tőke

  DOI：10.1016/j.tet.2004.08.026

  日期：2004.10

  The first examples of the 1,7-electrocyclization of azomethine ylides onto a nitro group, to give benz-1,2,6-oxadiazepine intermediates are reported. Subsequent ring contraction results in the formation of indazole-N-oxides. (C) 2004 Elsevier Ltd. All rights reserved.
• 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.