2-(trifluoroacetoxy)-2,3,4,5,6,7-hexahydro-1H-cyclobuta[5,6]cyclohepta[7,8]naphtho[2,3-d][1,3]dioxol-1-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(trifluoroacetoxy)-2,3,4,5,6,7-hexahydro-1H-cyclobuta[5,6]cyclohepta[7,8]naphtho[2,3-d][1,3]dioxol-1-one
• 英文别名: (3-Oxo-16,18-dioxapentacyclo[11.7.0.02,5.06,12.015,19]icosa-1(20),2(5),6(12),13,15(19)-pentaen-4-yl) 2,2,2-trifluoroacetate
• 化学式: C₂₀H₁₅F₃O₅
• 分子量: 392.331
• InChiKey: XXQWLGXMEFDDQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  5-Cyclohept-1-enyl-benzo[1,3]dioxole 以 苯 为溶剂， 反应 1.17h， 生成 2-(trifluoroacetoxy)-2,3,4,5,6,7-hexahydro-1H-cyclobuta[5,6]cyclohepta[7,8]naphtho[2,3-d][1,3]dioxol-1-one
  参考文献：
  名称：

  Regioselective Annulation of Alicyclic−Aromatic Dienes with 3-Halo-3-cyclobutene-1,2-diones. Synthesis of Annulated α-Halobenzocyclobutenones¹

  摘要：

  4-(1-Cycloalken-1-yl)-1,2-dialkoxybenzenes 8, 10, and 11 and 5-(1-cycloalken-1-yl)-1,3-benzodioxoles 12-15 react with the semisquaric halides 5a and 5b in a dehydrative annulation process to give the annulated alpha-halobenzocyclobutenones 9a,b and 16a,b-21a,b in poor to good yields (20-76%). The reaction failed with alicyclic-aromatic dienes having no or only one alkoxy group in the benzene ring. The dehydrative annulation process could be extended to 4-(3,4-dimethoxyphenyl)-1,2-dihydronaphthalene (24), affording the highly annulated alpha-chlorobenzocyclobutenone 25 in 50% yield. In the case of 5-(1-cyclobuten-1-yl)-1,3-benzodioxole (22), reaction with the semisquaric halides 5a,b yielded the dicyclobutanaphthodioxole-1,2-dione (23) as the sole product in a dehydrochlorinative annulation process. A reaction pathway has been suggested for the dehydrative annulation process. Several of the annulated alpha-halobenzocyclobutenones prepared were submitted to selected chemical transformations. Thus, the reaction with tributyltin hydride afforded the annulated benzocyclobutenones 26a-f in excellent yields (74-78%), and treatment with silver trifluoroacetate afforded the alpha-(trifluoroacetoxy)benzocyclobutenones 27a-c in 71-79% yields.

  DOI：

  10.1021/jo971948n

文献信息

• Regioselective Annulation of Alicyclic−Aromatic Dienes with 3-Halo-3-cyclobutene-1,2-diones. Synthesis of Annulated α-Halobenzocyclobutenones¹
  作者：Arthur H. Schmidt、Gunnar Kircher、Elmar Bräu

  DOI：10.1021/jo971948n

  日期：1998.3.1

  4-(1-Cycloalken-1-yl)-1,2-dialkoxybenzenes 8, 10, and 11 and 5-(1-cycloalken-1-yl)-1,3-benzodioxoles 12-15 react with the semisquaric halides 5a and 5b in a dehydrative annulation process to give the annulated alpha-halobenzocyclobutenones 9a,b and 16a,b-21a,b in poor to good yields (20-76%). The reaction failed with alicyclic-aromatic dienes having no or only one alkoxy group in the benzene ring. The dehydrative annulation process could be extended to 4-(3,4-dimethoxyphenyl)-1,2-dihydronaphthalene (24), affording the highly annulated alpha-chlorobenzocyclobutenone 25 in 50% yield. In the case of 5-(1-cyclobuten-1-yl)-1,3-benzodioxole (22), reaction with the semisquaric halides 5a,b yielded the dicyclobutanaphthodioxole-1,2-dione (23) as the sole product in a dehydrochlorinative annulation process. A reaction pathway has been suggested for the dehydrative annulation process. Several of the annulated alpha-halobenzocyclobutenones prepared were submitted to selected chemical transformations. Thus, the reaction with tributyltin hydride afforded the annulated benzocyclobutenones 26a-f in excellent yields (74-78%), and treatment with silver trifluoroacetate afforded the alpha-(trifluoroacetoxy)benzocyclobutenones 27a-c in 71-79% yields.