8-bromo-1-carbomethoxy-7-methylnaphthalene | 250716-81-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 8-bromo-1-carbomethoxy-7-methylnaphthalene
• 英文别名: Methyl 8-bromo-7-methylnaphthalene-1-carboxylate
• CAS: 250716-81-5
• 化学式: C₁₃H₁₁BrO₂
• 分子量: 279.133
• InChiKey: QPOHNXXKFNKHQQ-UHFFFAOYSA-N

物化性质

• 熔点：
  70-72 °C
• 沸点：
  372.8±22.0 °C(Predicted)
• 密度：
  1.439±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 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：

  8-bromo-1-carbomethoxy-7-methylnaphthalene 在 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以82%的产率得到8-bromo-7-methyl-1-naphthalenecarboxylic acid
  参考文献：
  名称：

  Synthesis of 8,8‘-Disubstituted 1,1‘-Binaphthyls Stable to Atropisomerization:  2,2‘-Dimethyl-1,1‘-binaphthalene-8,8‘-diol and 2,2‘-Dimethyl-8,8‘-bis(4-tert-butyloxazolyl)-1,1‘-binaphthyl

  摘要：

  Axially chiral binaphthyls 3a and 3b were synthesized taking, advantage of Ullman coupling of 4a and 4b, respectively. The binaphthyls were shown to be stable to atropisomerization. Binaphthol 3b was resolved with (-)-(1S)-menthyl chloroformate (11). R-axis diastereomer of bisoxazoline 3b was used for enantioselective cyclopropanation of styrene with ethyl diazoacetate.

  DOI：

  10.1021/jo990968h
• 作为产物：
  描述：

  7-甲基-1-萘甲酸甲酯 在 N-溴代丁二酰亚胺(NBS) 、 硫酸 、 三氟乙酸 作用下， 以 溶剂黄146 为溶剂， 以94%的产率得到8-bromo-1-carbomethoxy-7-methylnaphthalene
  参考文献：
  名称：

  Synthesis of 8,8‘-Disubstituted 1,1‘-Binaphthyls Stable to Atropisomerization:  2,2‘-Dimethyl-1,1‘-binaphthalene-8,8‘-diol and 2,2‘-Dimethyl-8,8‘-bis(4-tert-butyloxazolyl)-1,1‘-binaphthyl

  摘要：

  Axially chiral binaphthyls 3a and 3b were synthesized taking, advantage of Ullman coupling of 4a and 4b, respectively. The binaphthyls were shown to be stable to atropisomerization. Binaphthol 3b was resolved with (-)-(1S)-menthyl chloroformate (11). R-axis diastereomer of bisoxazoline 3b was used for enantioselective cyclopropanation of styrene with ethyl diazoacetate.

  DOI：

  10.1021/jo990968h

文献信息

• Synthesis of 8,8‘-Disubstituted 1,1‘-Binaphthyls Stable to Atropisomerization:  2,2‘-Dimethyl-1,1‘-binaphthalene-8,8‘-diol and 2,2‘-Dimethyl-8,8‘-bis(4-<i>tert</i>-butyloxazolyl)-1,1‘-binaphthyl
  作者：Sergei V. Kolotuchin、Albert I. Meyers

  DOI：10.1021/jo990968h

  日期：1999.10.1

  Axially chiral binaphthyls 3a and 3b were synthesized taking, advantage of Ullman coupling of 4a and 4b, respectively. The binaphthyls were shown to be stable to atropisomerization. Binaphthol 3b was resolved with (-)-(1S)-menthyl chloroformate (11). R-axis diastereomer of bisoxazoline 3b was used for enantioselective cyclopropanation of styrene with ethyl diazoacetate.