2-bromo-6-methoxynaphthalene-1-carbaldehyde | 570390-58-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-bromo-6-methoxynaphthalene-1-carbaldehyde
• 英文别名: 2-bromo-6-methoxy-1-naphthaldehyde；2-Bromo-6-methoxy-1-naphthaldehyde
• CAS: 570390-58-8
• 化学式: C₁₂H₉BrO₂
• 分子量: 265.106
• InChiKey: UXQWYOQUSVALSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2913000090

反应信息

• 作为反应物：
  描述：

  2-bromo-6-methoxynaphthalene-1-carbaldehyde 在 sodium tetrahydroborate 、 sodium acetate 、 palladium diacetate 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  Palladium-catalyzed and KO Bu-promoted Caryl–Oalcoholic coupling: an efficient one-pot synthesis of oxygen containing fused rings

  摘要：

  An efficient one-pot synthetic method has been developed for the synthesis of oxygen containing fused rings from 2'-bromo-biaryl-2-carbaldehyde via tandem reduction followed by palladium-catalyzed and (KOBu)-Bu-t-promoted C-aryl-O-alcoholic coupling. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.01.062
• 作为产物：
  描述：

  2-bromo-3,4-dihydro-6-methoxy-1-naphthaldehyde 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯 为溶剂， 反应 12.0h， 生成 2-bromo-6-methoxynaphthalene-1-carbaldehyde
  参考文献：
  名称：

  钯催化的一锅Suzuki偶联反应，然后将芳基钯加成醛：一种发荧光的9-一衍生物的简便方法

  摘要：

  通过一锅反应，包括2-溴苯基硼酸与2-溴甲醛的顺序Suzuki偶联，然后向醛中分子内芳基钯的加法反应，可以高效地制备各种芴-9-一衍生物。

  DOI：

  10.1016/j.tetlet.2010.08.062

文献信息

• Substituted benzo[i]phenanthridines as mammalian topoisomerase-Targeting agents
  作者：Darshan Makhey、Dajie Li、Baoping Zhao、Sai-Peng Sim、Tsai-Kun Li、Angela Liu、Leroy F Liu、Edmond J LaVoie

  DOI：10.1016/s0968-0896(03)00053-1

  日期：2003.4

  benzo[i]phenanthridines were synthesized as potential bioisosteres of nitidine and its analogues. In the present study, 2,3-methylenedioxy-8,9-dimethoxybenzo[i]phenanthridine, 2,3-methylenedioxy-8,9-dimethoxy-5-methylbenzo[i]phenanthridine, 2,3,8,9-tetramethoxybenzo[i]phenanthridine and 5-methyl-2,3,8,9-tetramethoxybenzo[i]phenanthridine were synthesized. These benzo[i]phenanthridine derivatives were

  已知在拓扑异构酶I或II的存在下，几种苯并[c]菲啶和原小ber碱生物碱，如亚尼替丁和小ber红素，可诱导DNA裂解。对与苯并[c]菲啶和原小ber碱生物碱相关的各种类似物进行的结构活性研究，为了解影响这种拓扑异构酶靶向活性的结构特征提供了见识。苯并[c]菲啶和原小ber碱生物碱的A环内的修饰可显着改变其增强DNA和拓扑异构酶之间可裂解复合物形成的能力。合成了选定的苯并[i]菲啶作为亚硝胺及其类似物的潜在生物等排体。在本研究中，2,3-亚甲基二氧基-8,9-二甲氧基苯并[i]菲啶，2,3-亚甲基二氧基-8,9-二甲氧基-5-甲基苯并[i]菲啶 合成了2,3,8,9-四甲氧基苯并[i]菲啶和5-甲基-2,3,8,9-四甲氧基苯并[i]菲啶。评价这些苯并[i]菲啶衍生物在拓扑异构酶和DNA存在下增强可裂解复合物形成的能力，以及它们对人淋巴母细胞瘤细胞系RPMI8402的细胞毒性。2,3-亚甲基二氧基-8
• Palladium-catalyzed one-pot Suzuki–Miyaura cross coupling followed by oxidative lactonization: a novel and efficient route for the one-pot synthesis of benzo[c]chromene-6-ones
  作者：Raju Singha、Soumyabrata Roy、Sukla Nandi、Priyanka Ray、Jayanta K. Ray

  DOI：10.1016/j.tetlet.2012.11.144

  日期：2013.2

  A number of 6H-benzo[c]chromene-6-ones, 5H-naphtho[1,2-c]chrome-5-ones, and 6H-naphtho[2,1-c]chromene-6-one have been synthesized starting with 2-hydroxyphenylboronic acid and o-bromobenzaldehyde or o-bromonaphthalene carboxaldehyde derivatives via a one-pot Suzuki-Miyaura cross coupling followed by oxidative lactonization reactions. The overall transformation consists of three reactions: Suzuki-Miyaura cross coupling, hemi-acetal formation, and oxidation. (c) 2012 Elsevier Ltd. All rights reserved.
• Asymmetric Allylation/Pauson–Khand Reaction: A Simple Entry to Polycyclic Amines. Application to the Synthesis of Aminosteroid Analogues
  作者：Santos Fustero、Rubén Lázaro、Nuria Aiguabella、Antoni Riera、Antonio Simón-Fuentes、Pablo Barrio

  DOI：10.1021/ol500142c

  日期：2014.2.21

  Asymmetric allylation of o-iodoarylsulfinylimines has been achieved in high diastereoselectivities. The thus-obtained o-iodoarylhomoallylic sulfinamides participate in a subsequent Sonogashira coupling followed by a diastereoselective intramolecular Pauson-Khand reaction. In this way, tricyclic amines showing a unique benzo-fused indenyl backbone were obtained. The methodology has been applied to the synthesis of amino steroid analogues.
• 8,9-Methylenedioxybenzo[i]phenanthridines
  作者：Dajie Li、Baoping Zhao、Sai-Peng Sim、Tsai-Kun Li、Angela Liu、Leroy F Liu、Edmond J LaVoie

  DOI：10.1016/s0968-0896(03)00394-8

  日期：2003.8

  Substituted benzo[i]phenanthridines that have incorporated within their structure an 8,9-methylenedioxy group can exhibit topoisornerase I-targeting activity. Structure-activity studies were performed to examine the influence of saturation at the 11,12-positions of several substituted 8,9-methylenedioxybenzo[i]phenanthridines. The activities of these dihydro analogues were compared to those of their unsaturated analogues. In addition, the influence of varying substituents at the 2- and 3-positions within the A-ring of these 8,9-methylenedioxybenzo[i]phenanthridines on their relative potency as topoisomerase I-targeting agents and cell proliferation as determined using the MTT assay was investigated. 2,3-Dimethoxy-8,9-methylenedioxybenzo[i]phenanthridine and its 11,12-dihydro derivative were among the more potent analogues evaluated with regard to topoisomerase I-targeting activity and cytotoxicity. (C) 2003 Elsevier Ltd. All rights reserved.
• RECOVERY AND RECYCLE OF CATALYST COMPONENTS USED IN PALLADIUM-CATALYZED PREPARATION OF ARYLCARBOXYLIC ACIDS
  申请人：ALBEMARLE CORPORATION

  公开号：EP1025074A1

  公开（公告）日：2000-08-09