2-bromo-3,4-dihydro-6-methoxy-1-naphthaldehyde | 118904-34-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-bromo-3,4-dihydro-6-methoxy-1-naphthaldehyde
• 英文别名: 2-bromo-6-methoxy-3,4-dihydronaphthalene-1-carbaldehyde；2-bromo-3,4-dihydro-6-methoxynaphthalene-1-carbaldehyde
• CAS: 118904-34-0
• 化学式: C₁₂H₁₁BrO₂
• 分子量: 267.122
• InChiKey: WRZBYJPBWIPCLZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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-3,4-dihydro-6-methoxy-1-naphthaldehyde 在 四(三苯基膦)钯 氯化亚砜 、 magnesium 、 zinc dibromide 作用下， 反应 5.5h， 生成 6-methoxy-2-phenyl-1-vinyl-3,4-dihydronaphthalene
  参考文献：
  名称：

  Gilchrist, Thomas L.; Summersell, Richard J., Journal of the Chemical Society. Perkin transactions I, 1988, p. 2595 - 2602

  摘要：

  DOI：
• 作为产物：
  描述：

  6-甲氧基-3,4-二氢-1H-2-萘酮 、 N,N-二甲基甲酰胺 在 三溴化磷 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以50%的产率得到2-bromo-3,4-dihydro-6-methoxy-1-naphthaldehyde
  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

• 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。
• 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.
• A simple route to 9-fluorenylidenes by domino Suzuki/Heck coupling reactions
  作者：Sunanda Paul、Tumpa Gorai、Arijit Koley、Jayanta K. Ray

  DOI：10.1016/j.tetlet.2011.05.148

  日期：2011.8

  A palladium catalyzed domino intermolecular Suzuki followed by intramolecular Heck coupling is described. This strategy afforded a novel and convenient synthesis of various 9-fluorenylidene derivatives in one-pot under relatively mild reaction condition. (C) 2011 Elsevier Ltd. All rights reserved.
• Formation of a 12-aza steroid by 1 -aza triene cyclisation
  作者：Thomas L. Gilchrist、Maureen A. M. Healy

  DOI：10.1039/p19920000749

  日期：——

  An approach to 12-aza analogues of estrone is described in which ring C is for
• GILCHRIST, THOMAS L.;SUMMERSELL, RICHARD J., J. CHEM. SOC. PERKIN TRANS. PT 1,(1988) N 9, C. 2595-2601
  作者：GILCHRIST, THOMAS L.、SUMMERSELL, RICHARD J.

  DOI：——

  日期：——