6,7-dimethoxy-1-(5-methoxy-2-nitrophenyl)-3,4-dihydroisoquinoline | 103771-56-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6,7-dimethoxy-1-(5-methoxy-2-nitrophenyl)-3,4-dihydroisoquinoline
• 英文别名: 6,7-Dimethoxy-1-(5-methoxy-2-nitrophenyl)-3,4-dihydroisoquinoline
• CAS: 103771-56-8
• 化学式: C₁₈H₁₈N₂O₅
• 分子量: 342.351
• InChiKey: OKDUOAFKJURUCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  85.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6,7-dimethoxy-1-(5-methoxy-2-nitrophenyl)-3,4-dihydroisoquinoline 在 tin(ll) chloride 作用下， 以 乙酸乙酯 为溶剂， 以74%的产率得到1-(2-amino-5-methoxyphenyl)-6,7-dimethoxy-3,4-dihydroisoquinoline
  参考文献：
  名称：

  1-（2-氨基苯基）异喹啉的合成及其顺式-二氯铂（II）配合物的生物活性。

  摘要：

  异喹啉的广泛生物学效应促使我们将其用作顺铂（II）抗肿瘤复合物中的螯合，非离去配体。报道了几种具有不同氢化度和苯环取代基的1-（2-氨基苯基）异喹啉衍生物的合成。这些化合物构成了用于合成低环铂（II）配合物的一类新的配体。体外细胞毒性测试表明，最碱性的胺配体提供了最有效的配合物。与成熟的抗肿瘤化合物顺铂相比，其中两个新的复合物对L1210鼠白血病细胞更有效。

  DOI：

  10.1021/jm980434t
• 作为产物：
  描述：

  5-甲氧基-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 6,7-dimethoxy-1-(5-methoxy-2-nitrophenyl)-3,4-dihydroisoquinoline
  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

• Divergent Syntheses of Pyridoacridine Alkaloids <i>via</i> <scp>Palladium‐Catalyzed</scp> Reductive Cyclization with <scp>Nitro‐Biarenes</scp>
  作者：Bo Liu、Shuping Wang、Changhao Bian、Hongze Liao、Hou‐Wen Lin

  DOI：10.1002/cjoc.202100094

  日期：2021.7

  A divergent and novel protocol for the preparation of both pyrido[2,3,4-kl]acridine and pyrido[4,3,2-kl]acridine alkaloids was developed. This method featured the remote palladium-catalyzed reductive cyclization with Mo(CO)6 as reductant. A wide range of substrates including three types of nitro arenes were tolerated and afforded corresponding products in good to excellent yields. This method has been

  开发了一种用于制备吡啶并[2,3,4- kl ]吖啶和吡啶并[4,3,2- kl ]吖啶生物碱的新方案。该方法的特点是使用 Mo(CO) 6作为还原剂进行远程钯催化的还原环化反应。包括三种硝基芳烃在内的各种底物都可以耐受，并以良好到极好的产率提供相应的产品。该方法已成功应用于去甲西哥林、苯乙烯胺C和necatorone骨架的全合成。
• A Very Mild Access to 3,4-Dihydroisoquinolines Using Triphenyl Phosphite-Bromine-Mediated Bischler-Napieralski-Type Cyclization
  作者：Fabio Prati、Daniele Vaccari、Paolo Davoli、Claudia Ori、Alberto Spaggiari

  DOI：10.1055/s-0028-1083544

  日期：——

  Substituted β-phenylethylamides undergo smooth intramolecular cyclization to 3,4-dihydroisoquinolines in good to excellent yields when treated with bromotriphenoxyphosphonium bromide at -60 ˚C in dichloromethane in the presence of triethyl­amine. The reaction proceeds under the mildest conditions ever reported for Bischler-Napieralski-type cyclizations. When chlorotriphenoxyphosphonium choride is used, low yields are obtained instead.

  被取代的β-苯乙酰胺类化合物在-60 °C二氯甲烷中以三乙胺作为催化剂的条件下，与溴三苯氧基膦溴处理时，能以良好至优异的产率顺利进行分子内环化反应生成3,4-二氢异喹啉。此反应是在目前已报道的比什勒-纳皮亚尔斯基型环化反应中条件最为温和的。而若使用氯三苯氧基膦氯时，则产率较低。
• 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。
• The synthesis of N-phenoxyethyl-1-substituted-1,2,3,4-tetrahydroisoquinolines and their α1-adrenoceptor blocking activity
  作者：Chen-Yuan Kuo、Ming-Jung Wu

  DOI：10.1016/j.ejmech.2008.09.001

  日期：2009.3

  A series of phenoxyisoquinolines, N-phenoxyethyl-1-(2-nitrophenyl)-1,2,3,4-THIQS 3a-3d, N-phenoxyethyl-1-benzyl-1,2,3,4-THIQ 3e, N-phenoxyethyl-1-(2-aminophenyl)-1,2,3,4-THIQs 5f'-5i', N-phenoxyethyl-1-(2- phenoxyethylaminophenyl)-1,2,3,4-THIQs 5f'-5i', have been synthesized and tested in isolated rat vas deferens alpha-adrenoreceptors. Comparison of pA2 values for these compounds in the presence of phenylephrine confirms that alpha(1)-adrenoceptor blocking activity of 3a-3d (-NO2 series) is more active than 6a-6c (-NH2 series) in the aortic rings isolated from SD rats. On the other hand, the electron-donating group at the 6-position of isoquinoline ring either increases or decreases the alpha(1)-adrenoceptor blocking activity. (C) 2008 Elsevier Masson SAS. 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.