1-bromo-6,7-dimethoxy-3,4-dihydronaphthalene-2-carbaldehyde | 883221-01-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-bromo-6,7-dimethoxy-3,4-dihydronaphthalene-2-carbaldehyde
• 英文别名: 6,7-dimethoxy-1-bromo-3,4-dihydro-2-naphthaldehyde；1-Bromo-6,7-dimethoxy-3,4-dihydronaphthalene-2-carbaldehyde
• CAS: 883221-01-0
• 化学式: C₁₃H₁₃BrO₃
• 分子量: 297.148
• InChiKey: ZIAGKZLBXCTGKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-bromo-6,7-dimethoxy-3,4-dihydronaphthalene-2-carbaldehyde 在 selenium 作用下， 以 二甲基亚砜 为溶剂， 反应 0.08h， 以64%的产率得到1-bromo-6,7-dimethoxy-2-naphthaldehyde
  参考文献：
  名称：

  Tetralones作为合成2,2'-双取代1,1'-联萘的前体及相关化合物

  摘要：

  本文以四氢萘酮为起始原料，描述了联芳基化合物的合成。首先将四氢萘酮转化为1-溴-3,4-二氢-2-萘甲醛，然后进行芳构化成相应的萘。然后将这些产物与在邻位含有取代基的各种芳香族硼酸进行铃木-宫浦交叉偶联反应，制得联芳基化合物。联芳基化合物具有含杂原子的取代基的邻位到新形成的二芳基轴。

  DOI：

  10.1016/j.tet.2008.08.079
• 作为产物：
  描述：

  6,7-二甲氧基-3,4-二氢-2H-1-萘酮 、 N,N-二甲基甲酰胺 在 三溴化磷 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 以63%的产率得到1-bromo-6,7-dimethoxy-3,4-dihydronaphthalene-2-carbaldehyde
  参考文献：
  名称：

  Methodology for the synthesis of 1,2-disubstituted arylnaphthalenes from α-tetralones

  摘要：

  alpha-Tetralones were initially converted into 1-bromo-dihydronaphthalene-2-carbaldehydes and 1-bromo-naphthalene-2carbaldehydes. These precursors were then subjected to Suzuki coupling reactions to afford 1,2-disubstituted aryldihydronaphthalenes and 1,2-disubstituted arylnaphthalenes, respectively. The former products were oxidized with DDQ to give 1,2-disubstituted arylnaphthalenes. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.01.013

文献信息

• One-pot synthesis of isoquinoline and related compounds via Cu-mediated tandem cross-coupling and cyclization
  作者：Shubhendu Dhara、Raju Singha、Yasin Nuree、Jayanta K. Ray

  DOI：10.1016/j.tetlet.2013.11.088

  日期：2014.1

  One-pot synthetic strategy has been developed to access isoquinolines and its analogs via Cu-mediated tandem cross-coupling and cyclization in good yields under mild reaction conditions. A mixture of suitably substituted α-bromoaldehyde, terminal alkyne, and aq NH3 in CuI/1,10-phenanathroline catalytic system afforded the 3-substituted isoquinoline regio-selectively in good to excellent yields.

  已经开发出一锅合成策略，以在温和的反应条件下通过铜介导的串联交叉偶联和环化以高收率获得异喹啉及其类似物。在CuI / 1，10-菲咯啉催化体系中适当取代的α-溴醛，末端炔烃和NH 3水溶液的混合物以良好或优异的收率选择性地生成3-取代的异喹啉。
• Tetralones as precursors for the synthesis of 2,2′-disubstituted 1,1′-binaphthyls and related compounds
  作者：Simon S. Moleele、Joseph P. Michael、Charles B. de Koning

  DOI：10.1016/j.tet.2008.08.079

  日期：2008.11

  Using tetralones as starting materials, the synthesis of biaryl compounds is described in this paper. The tetralones were initially converted into 1-bromo-3,4-dihydro-2-naphthalenecarbaldehydes before effecting aromatization into the corresponding naphthalenes. These products were then subjected to Suzuki–Miyaura cross-coupling reactions, with a variety of aromatic boronic acids containing substituents

  本文以四氢萘酮为起始原料，描述了联芳基化合物的合成。首先将四氢萘酮转化为1-溴-3,4-二氢-2-萘甲醛，然后进行芳构化成相应的萘。然后将这些产物与在邻位含有取代基的各种芳香族硼酸进行铃木-宫浦交叉偶联反应，制得联芳基化合物。联芳基化合物具有含杂原子的取代基的邻位到新形成的二芳基轴。
• Methodology for the synthesis of 1,2-disubstituted arylnaphthalenes from α-tetralones
  作者：Simon S. Moleele、Joseph P. Michael、Charles B. de Koning

  DOI：10.1016/j.tet.2006.01.013

  日期：2006.3

  alpha-Tetralones were initially converted into 1-bromo-dihydronaphthalene-2-carbaldehydes and 1-bromo-naphthalene-2carbaldehydes. These precursors were then subjected to Suzuki coupling reactions to afford 1,2-disubstituted aryldihydronaphthalenes and 1,2-disubstituted arylnaphthalenes, respectively. The former products were oxidized with DDQ to give 1,2-disubstituted arylnaphthalenes. (c) 2006 Elsevier Ltd. All rights reserved.