2-bromo-7-methoxynaphthalene-1-carbaldehyde | 570390-59-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-bromo-7-methoxynaphthalene-1-carbaldehyde
• 英文别名: 2-bromo-7-methoxy-1-naphthaldehyde；2-Bromo-7-methoxynaphthalene-1-carbaldehyde
• CAS: 570390-59-9
• 化学式: C₁₂H₉BrO₂
• 分子量: 265.106
• InChiKey: KWTVMOGTPSONRB-UHFFFAOYSA-N

物化性质

• 熔点：
  132-134 °C
• 沸点：
  384.7±22.0 °C(Predicted)
• 密度：
  1.511±0.06 g/cm3(Predicted)

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

反应信息

• 作为反应物：
  描述：

  2-bromo-7-methoxynaphthalene-1-carbaldehyde 在 sodium tetrahydroborate 、 trans-bis(triphenylphosphine)palladium dichloride 、 potassium tert-butylate 、 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 7.0h， 生成 2-methoxy-5H-6-oxa-chrysene
  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：

  7-甲氧基-2-萘满酮 在 三溴化磷 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 氯仿 、 甲苯 为溶剂， 反应 17.0h， 生成 2-bromo-7-methoxynaphthalene-1-carbaldehyde
  参考文献：
  名称：

  取代苯并[i]菲啶作为哺乳动物拓扑异构酶靶向剂。

  摘要：

  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

  DOI：

  10.1016/s0968-0896(03)00053-1

文献信息

• Synthesis of phenanthridine and its analogues via aerobic ligand-free domino Suzuki coupling–Michael addition reaction catalyzed by in situ generated palladium-nanoparticles in water
  作者：Munmun Ghosh、Atiur Ahmed、Shubhendu Dhara、Jayanta K. Ray

  DOI：10.1016/j.tetlet.2013.06.089

  日期：2013.9

  A convenient methodology has been developed towards the synthesis of substituted phenanthridines and analogous benzo[k] and benzo[i] derivatives via aerobic ligand-free domino Suzuki coupling–Michael addition reaction in the presence of Pd(OAc)2 and K3PO4 as a catalytic system in H2O at 90 °C in good yields. Reaction was believed to be catalyzed by in situ generated palladium nanoparticles in water

  在无Pd（OAc）2和K 3 PO 4存在下，通过无需氧配体多米诺Suzuki偶联-Michael加成反应，已经开发了一种便利的方法，用于合成取代的菲啶以及类似的苯并[ k ]和苯并[ i ]衍生物在90°C的H 2 O中用作催化体系，收率很高。据信该反应是通过在水中原位生成的钯纳米粒子并消除了丙酮来催化的。
• Palladium-catalyzed one-pot Suzuki coupling followed by arylpalladium addition to aldehyde: a convenient route to fluoren-9-one derivatives
  作者：Sunanda Paul、Shubhankar Samanta、Jayanta K. Ray

  DOI：10.1016/j.tetlet.2010.08.062

  日期：2010.10

  Various fluoren-9-one derivatives were prepared efficiently by a one-pot reaction involving sequential Suzuki coupling of 2-bromophenyl boronic acid with 2-bromocarboxaldehyde followed by intramolecular arylpalladium addition to aldehyde.

  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。
• Synthesis of Phenanthridines and Analogues via Suzuki Coupling and Condensation
  作者：Jayanta Ray、Shubhendu Dhara、Munmun Ghosh

  DOI：10.1055/s-0033-1339793

  日期：——

  A convenient and short methodology has been developed towards the synthesis of highly substituted phenanthridines and their analogous benzo[k] and benzo[i] derivatives in a single step via Suzuki coupling and condensation between suitably substituted aromatic ortho-bromoaldehydes and ortho-aminobenzeneboronic acids in good to excellent yields.

  已开发出一种方便且简短的方法，通过适当取代的芳香族邻溴醛和邻氨基苯硼酸之间的 Suzuki 偶联和缩合，一步合成高度取代的菲啶及其类似的苯并 [k] 和苯并 [i] 衍生物。良好的产量。
• Aerobic ligand-free domino Suzuki coupling—Michael addition reaction catalyzed by in situ generated palladium nanoparticles in water: a general method for the synthesis of benzo[c]chromene derivatives
  作者：Atiur Ahmed、Yasin Nuree、Jayanta K. Ray

  DOI：10.1016/j.tetlet.2012.12.005

  日期：2013.2

  A general method has been developed for the synthesis of benzo[c]chromene derivatives via aerobic ligand-free domino Suzuki coupling and Michael addition reaction catalyzed by in situ generated palladium nanoparticles in water leading to C–C and C–O bond formations simultaneously.

  已开发出一种通过无氧配体多米诺Suzuki偶联和水中原位生成的钯纳米粒子催化的Michael加成反应合成苯并[ c ]苯甲基衍生物的通用方法，该反应同时导致C–C和C–O键的形成。
• 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.