8'-(2-Methoxy-naphthalen-1-yl)-3',4'-dihydro-1'H-spiro[[1,3]dioxolane-2,2'-naphthalene] | 887771-43-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 8'-(2-Methoxy-naphthalen-1-yl)-3',4'-dihydro-1'H-spiro[[1,3]dioxolane-2,2'-naphthalene]
• 英文别名: 5'-(2-methoxynaphthalen-1-yl)spiro[1,3-dioxolane-2,3'-2,4-dihydro-1H-naphthalene]
• CAS: 887771-43-9
• 化学式: C₂₃H₂₂O₃
• 分子量: 346.426
• InChiKey: WSDNGGZOGXOKBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8'-(2-Methoxy-naphthalen-1-yl)-3',4'-dihydro-1'H-spiro[[1,3]dioxolane-2,2'-naphthalene] 在 盐酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以98%的产率得到8-(2-methoxy-1-naphthyl)-2-tetralone
  参考文献：
  名称：

  General Synthesis of 8-Aryl-2-tetralones

  摘要：

  Two alternative routes are described for the synthesis of 8-aryl-2-tetralones (1). Route A starts from alpha-tetralone 3 and involves 3 or 4 steps, with the selective Na-EtOH reduction of 1-aryl-7-methoxynaphthalenes 2 being the key step. The exclusive reduction of the A ring of naphthalenes 2 occurs when the aryl group at C-1 has no substituent at the ortho positions, affording tetrahydronaphthalenes 11. Reduction of the B ring of 2 becomes the major process when the aryl fragment has two substituents at the ortho positions, affording 8-aryl-2-tetralones 1 as the major component. Route B involves 5 steps starting from 2-tetralone 5, with the key step being the Suzuki coupling with triflate 4. This approach allows the synthesis of 8-aryl-2-tetralones 1 with no substituent at the ortho positions of the aryl fragment and with naphthalene and anthracene rings at C-8.

  DOI：

  10.1021/jo060688j
• 作为产物：
  描述：

  spiro<(1,3-dioxocyclopentane)-2,2'-(8'-methoxy-1',2',3',4'-tetrahydronaphthalene)> 在 四(三苯基膦)钯 吡啶 、 barium dihydroxide 、 正丁基锂 、 二苯基膦 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 49.0h， 生成 8'-(2-Methoxy-naphthalen-1-yl)-3',4'-dihydro-1'H-spiro[[1,3]dioxolane-2,2'-naphthalene]
  参考文献：
  名称：

  General Synthesis of 8-Aryl-2-tetralones

  摘要：

  Two alternative routes are described for the synthesis of 8-aryl-2-tetralones (1). Route A starts from alpha-tetralone 3 and involves 3 or 4 steps, with the selective Na-EtOH reduction of 1-aryl-7-methoxynaphthalenes 2 being the key step. The exclusive reduction of the A ring of naphthalenes 2 occurs when the aryl group at C-1 has no substituent at the ortho positions, affording tetrahydronaphthalenes 11. Reduction of the B ring of 2 becomes the major process when the aryl fragment has two substituents at the ortho positions, affording 8-aryl-2-tetralones 1 as the major component. Route B involves 5 steps starting from 2-tetralone 5, with the key step being the Suzuki coupling with triflate 4. This approach allows the synthesis of 8-aryl-2-tetralones 1 with no substituent at the ortho positions of the aryl fragment and with naphthalene and anthracene rings at C-8.

  DOI：

  10.1021/jo060688j

文献信息

• General Synthesis of 8-Aryl-2-tetralones
  作者：M. Carmen Carreño、Marcos González-López、Alfonso Latorre、Antonio Urbano

  DOI：10.1021/jo060688j

  日期：2006.6.1

  Two alternative routes are described for the synthesis of 8-aryl-2-tetralones (1). Route A starts from alpha-tetralone 3 and involves 3 or 4 steps, with the selective Na-EtOH reduction of 1-aryl-7-methoxynaphthalenes 2 being the key step. The exclusive reduction of the A ring of naphthalenes 2 occurs when the aryl group at C-1 has no substituent at the ortho positions, affording tetrahydronaphthalenes 11. Reduction of the B ring of 2 becomes the major process when the aryl fragment has two substituents at the ortho positions, affording 8-aryl-2-tetralones 1 as the major component. Route B involves 5 steps starting from 2-tetralone 5, with the key step being the Suzuki coupling with triflate 4. This approach allows the synthesis of 8-aryl-2-tetralones 1 with no substituent at the ortho positions of the aryl fragment and with naphthalene and anthracene rings at C-8.