2-Methoxy-1-i-propoxy-4-(1-propenyl)benzol | 29653-00-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-Methoxy-1-i-propoxy-4-(1-propenyl)benzol
• 英文别名: 3-methoxy-4-isopropyloxy-1-trans-propenyl-benzene；3-Methoxy-4-isopropyloxy-1-(propen-(1)-yl-(1t))-benzol；3-Methoxy-4-isopropyloxy-1-trans-propenyl-benzol；2-methoxy-1-propan-2-yloxy-4-[(E)-prop-1-enyl]benzene
• CAS: 29653-00-7
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: AONZZPUKSBPSTK-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Methoxy-1-i-propoxy-4-(1-propenyl)benzol 、 Semisquaric chloride 以9%的产率得到7-Isopropoxy-6-methoxy-3-methyl-3,4-dihydro-cyclobuta[a]naphthalene-1,2-dione
  参考文献：
  名称：

  Oxokohlenstoffe und verwandte Verbindungen. 27. Synthese von Dihydrocyclobuta[a]naphthalen-1,2-dionen und Cyclobuta[a]naphthalen-1,2-dionen durch Anellierung von Alkoxy-(1-alkenyl)benzolen mit 3-Chlor-3-cyclobuten-1,2-dion. Anwendungsbereich und Grenzen

  摘要：

  The reaction of alkoxy-(1-alkenyl)benzenes with semisquaric chloride (3) has been investigated systematically. 1,2-Dialkoxy- and 1-alkoxy'-2-alkoxy ''-4-(1-alkenyl)benzenes (6a-j) and (11a-i) react with 3 to give the 3,4-dihydrocyclobuta[a]naphthalene-1,2-diones (8a-j) and (12a-i). Treatment of the dihydrocyclobuta[a]naphthalene-1,2-diones with 1.2 equiv. bromine effects dehydrogenation and affords cyclobuta[a] naphthalene-1,2-diones (9a-e) and (13b-f). Any efforts to extend this annulation reaction to dimethoxy-(l-alkenyl)benzenes with the methoxy groups in other than the 1,2-positions, e. g. 14a, b, 16a, b have been unsuccessful. The reaction of 1,2,3-trimethoxy-4-(l-propenyl) [and 4-(1-butenyl)]-benzenes (18a) and (18b) with semisquaric chloride (3) leads to the elimination of HCl and CH3OH and gives 5,6-dimethoxy-3-methyl [and 3-ethyl]-cyclobuta[a]naphthalene-1,2-diones (20a) and (20b). The reaction pathway of this novel annulation reaction is discussed.

  DOI：

  10.1002/prac.199733901100
• 作为产物：
  描述：

  异丁香酚 、 2-溴丙烷 在 氢氧化钾 作用下， 以 异丙醇 为溶剂， 反应 1.5h， 生成 2-Methoxy-1-i-propoxy-4-(1-propenyl)benzol
  参考文献：
  名称：

  Oxokohlenstoffe und verwandte Verbindungen. 27. Synthese von Dihydrocyclobuta[a]naphthalen-1,2-dionen und Cyclobuta[a]naphthalen-1,2-dionen durch Anellierung von Alkoxy-(1-alkenyl)benzolen mit 3-Chlor-3-cyclobuten-1,2-dion. Anwendungsbereich und Grenzen

  摘要：

  The reaction of alkoxy-(1-alkenyl)benzenes with semisquaric chloride (3) has been investigated systematically. 1,2-Dialkoxy- and 1-alkoxy'-2-alkoxy ''-4-(1-alkenyl)benzenes (6a-j) and (11a-i) react with 3 to give the 3,4-dihydrocyclobuta[a]naphthalene-1,2-diones (8a-j) and (12a-i). Treatment of the dihydrocyclobuta[a]naphthalene-1,2-diones with 1.2 equiv. bromine effects dehydrogenation and affords cyclobuta[a] naphthalene-1,2-diones (9a-e) and (13b-f). Any efforts to extend this annulation reaction to dimethoxy-(l-alkenyl)benzenes with the methoxy groups in other than the 1,2-positions, e. g. 14a, b, 16a, b have been unsuccessful. The reaction of 1,2,3-trimethoxy-4-(l-propenyl) [and 4-(1-butenyl)]-benzenes (18a) and (18b) with semisquaric chloride (3) leads to the elimination of HCl and CH3OH and gives 5,6-dimethoxy-3-methyl [and 3-ethyl]-cyclobuta[a]naphthalene-1,2-diones (20a) and (20b). The reaction pathway of this novel annulation reaction is discussed.

  DOI：

  10.1002/prac.199733901100

文献信息

• West, Journal of the Chemical Society, 1945, p. 490
  作者：West

  DOI：——

  日期：——
• Oxokohlenstoffe und verwandte Verbindungen. 27. Synthese von Dihydrocyclobuta[a]naphthalen-1,2-dionen und Cyclobuta[a]naphthalen-1,2-dionen durch Anellierung von Alkoxy-(1-alkenyl)benzolen mit 3-Chlor-3-cyclobuten-1,2-dion. Anwendungsbereich und Grenzen
  作者：Arthur H. Schmidt、Gunnar Kircher、Mathias Spring、Markus W. Hendriok、Christian Künz

  DOI：10.1002/prac.199733901100

  日期：——

  The reaction of alkoxy-(1-alkenyl)benzenes with semisquaric chloride (3) has been investigated systematically. 1,2-Dialkoxy- and 1-alkoxy'-2-alkoxy ''-4-(1-alkenyl)benzenes (6a-j) and (11a-i) react with 3 to give the 3,4-dihydrocyclobuta[a]naphthalene-1,2-diones (8a-j) and (12a-i). Treatment of the dihydrocyclobuta[a]naphthalene-1,2-diones with 1.2 equiv. bromine effects dehydrogenation and affords cyclobuta[a] naphthalene-1,2-diones (9a-e) and (13b-f). Any efforts to extend this annulation reaction to dimethoxy-(l-alkenyl)benzenes with the methoxy groups in other than the 1,2-positions, e. g. 14a, b, 16a, b have been unsuccessful. The reaction of 1,2,3-trimethoxy-4-(l-propenyl) [and 4-(1-butenyl)]-benzenes (18a) and (18b) with semisquaric chloride (3) leads to the elimination of HCl and CH3OH and gives 5,6-dimethoxy-3-methyl [and 3-ethyl]-cyclobuta[a]naphthalene-1,2-diones (20a) and (20b). The reaction pathway of this novel annulation reaction is discussed.