1-(2-nitrophenyl)-3,4-dihydroisoquinoline | 19007-73-9

• 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: 1-(2-nitrophenyl)-3,4-dihydroisoquinoline
• CAS: 19007-73-9
• 化学式: C₁₅H₁₂N₂O₂
• mdl: MFCD07658210
• 分子量: 252.272
• InChiKey: GLMHXBPGCALECC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  58.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-nitrophenyl)-3,4-dihydroisoquinoline 在 盐酸 、 tin 、 乙醇 、 铁粉 、 溶剂黄146 作用下， 生成 1-(2-aminophenyl)-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Rodionow; Jaworskaja, Zhurnal Obshchei Khimii, 1943, vol. 13, p. 491,495

  摘要：

  DOI：
• 作为产物：
  描述：

  2-苯乙胺盐酸盐 在 sodium hydroxide 、 phosphorus pentoxide 、 xylene 作用下， 生成 1-(2-nitrophenyl)-3,4-dihydroisoquinoline
  参考文献：
  名称：

  Rodionow; Jaworskaja, Zhurnal Obshchei Khimii, 1943, vol. 13, p. 491,495

  摘要：

  DOI：

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 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。
• Photochromism of tetrahydroindolizines. Part XXVI: Mechanochemical synthesis, tunable photophysical properties and combined experimental and theoretical studies of novel photochromic tetrahydroindolizines
  作者：Saleh A. Ahmed、Nizar El Guesmi、Anas A.B. Alsulami、Ziad Moussa、Abdullah Y.A. Alzahrani、Rami J. Obaid、François Maurel、Aboel-Magd A. Abdel-Wahab

  DOI：10.1016/j.jphotochem.2022.114439

  日期：2023.3

  substituents in region C (base part) which include both electron donating and withdrawing groups in the ortho, meta and para positions of the phenyl ring. The absorption maxima (λmax) of both closed form (THI) and the colored form (betaine, after UV-irradiation) were spectrophotometrically determined in dichloromethane solution. The colored betaines displayed two absorption maxima, one between 472 and 485 nm

  在此，使用成熟的机械化学合成方法成功制备了 18 种新型光致变色四氢二氢吲嗪 (THI)。这些产品的收率非常好，而且纯化过程相对简单，没有任何分离挑战。新的 THI 在 C 区（碱基部分）包含各种取代基，其中包括苯环邻位、间位和对位的给电子基团和吸电子基团。吸收最大值 (λ max) 的封闭形式 (THI) 和有色形式（甜菜碱，在紫外线照射后）在二氯甲烷溶液中通过分光光度法测定。彩色甜菜碱显示出两个吸收最大值，一个在 472 和 485 nm 之间，第二个出现在 658 和 724 nm 之间的白色区域，拖尾延伸到近红外 (NIR) 区域。10'b-苯环中取代基的性质和位置对甜菜碱吸收的影响表明，吸收最大值在 658 和 690 nm 之间的邻位取代导致主要由空间效应引起的向色偏移THI 分子 10'b-苯环邻位取代基与间位和对位取代基的比较-吸收最大值在 700 和 724 nm 之间的
• Substituted Isoquinolines by Noyori Transfer Hydrogenation:  Enantioselective Synthesis of Chiral Diamines Containing an Aniline Subunit
  作者：E. Vedejs、P. Trapencieris、E. Suna

  DOI：10.1021/jo990594s

  日期：1999.9.1

  Transfer hydrogenation using the Noyori catalyst 5-Ts is effective for the enantioselective hydrogenation of imines containing fully substituted nitrogen groups (12 or 13). Analogues such as Ile could not be reduced in practical yield, apparently due to product inhibition of the catalyst. Asymmetric transfer hydrogenation of the aniline imine 8a was possible, but required. impractical purity levels for the substrate, and the nitro analogue 7 could not be reduced efficiently. The best results were Obtained with the bromophenyl imine 20, In the case of 20b, the product 21b was formed with 98.7% ee, and the material could be upgraded to >99% ee by crystallization of the hydrochloride salt. Reaction of 21b with NH3 or MeNH2 in the presence of Cu/CuCl gave the chiral anilines 10b or 23b. The latter substance is comparable to the commercially available 1 as a chiral proton donor fog amide enolates and provides access to the hitherto unavailable enantiomeric series.
• 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.