5-(1-cyclobuten-1-yl)-1,3-benzodioxole | 203377-85-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 5-(1-cyclobuten-1-yl)-1,3-benzodioxole
• 英文别名: 5-(Cyclobuten-1-yl)-1,3-benzodioxole
• CAS: 203377-85-9
• 化学式: C₁₁H₁₀O₂
• 分子量: 174.199
• InChiKey: LXFLNCNYVKEVTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  3-溴-3-环丁烯-1,2-二酮 、 5-(1-cyclobuten-1-yl)-1,3-benzodioxole 生成 2b,3,4,4a-tetrahydrodicyclobuta[5,6:7,8]naphtho[2,3-d][1,3]dioxole-1,2-dione
  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
• 作为产物：
  描述：

  1-(benzo[d][1,3]dioxol-5-yl)cyclobutanol 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 生成 5-(1-cyclobuten-1-yl)-1,3-benzodioxole
  参考文献：
  名称：

  布朗斯台德酸催化芳基环丁烯的马尔可夫尼科夫氢芳基化：生成宝石二芳基取代的环丁烷的路线

  摘要：

  使用布朗斯台德酸催化，通过质子化/弗里德尔-克拉夫茨序列开发了芳基环丁烯的区域选择性马尔可夫尼科夫加氢芳基化。与之前使用精心设计的芳基环丁烯和特定多氟化试剂的报道相比，无金属催化反应操作简单且可行，以良好至优异的收率提供了各种偕二芳基取代的芳基环丁烯。通过逐步控制实验探索了该反应的可能机制。该方案涉及偕二芳基取代的环丁烯支架中的吲哚，不仅丰富了布朗斯台德酸催化加氢芳基化的应用，而且为更广泛地获得潜在的生物活性环丁烷结构铺平了道路。

  DOI：

  10.1002/adsc.202400109

文献信息

• Preparation of Aryl Cyclobutenes Under Mild and Neutral Conditions
  作者：H. Juteau、Y. Gareau

  DOI：10.1080/00397919808004932

  日期：1998.10

  Aryl cyclobutyl acetates were converted to the corresponding aryl cyclobutenes with lithium bromide in good yields (50-97%) and in high purity.
• 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.
• 10.1002/adsc.202400109
  作者：Wang, Xiuhong、Sun, Zhening、Wang, Juanjuan、Zheng, Zhaojing、Lu, Hong、Wei, Hao

  DOI：10.1002/adsc.202400109

  日期：——

  A regioselective Markovnikov hydroarylation of arylcyclobutene has been developed using Brønsted acid catalysis through a protonation/Friedel‐Crafts sequence. The metal‐free catalytic reaction is operationally simple and feasible compared to previous reports that utilized elaborate arylcyclobutene and specific polyfluorinated reagents, affording a variety of gem‐diaryl‐ substituted arylcyclobutene

  使用布朗斯台德酸催化，通过质子化/弗里德尔-克拉夫茨序列开发了芳基环丁烯的区域选择性马尔可夫尼科夫加氢芳基化。与之前使用精心设计的芳基环丁烯和特定多氟化试剂的报道相比，无金属催化反应操作简单且可行，以良好至优异的收率提供了各种偕二芳基取代的芳基环丁烯。通过逐步控制实验探索了该反应的可能机制。该方案涉及偕二芳基取代的环丁烯支架中的吲哚，不仅丰富了布朗斯台德酸催化加氢芳基化的应用，而且为更广泛地获得潜在的生物活性环丁烷结构铺平了道路。