5,6-(methylenedioxy)benzocyclobutenone | 118112-19-9

• 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: 5,6-(methylenedioxy)benzocyclobutenone
• 英文别名: 2H-Cyclobuta[e][1,3]benzodioxol-7(6H)-one；6H-cyclobuta[g][1,3]benzodioxol-7-one
• CAS: 118112-19-9
• 化学式: C₉H₆O₃
• 分子量: 162.145
• InChiKey: ZKANRXBZUFUUTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,6-(methylenedioxy)benzocyclobutenone 在 正丁基锂 、 三氟乙酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.25h， 生成 2-ethenyl-2-hydroxy-6,7-(methylenedioxy)indan-1-one
  参考文献：
  名称：

  Acid-catalyzed ring expansion of 1-(1-methoxy-1,2-propadienyl)-2-cyclobuten-1-ols. Synthesis of 5-hydroxy-5-vinyl-2-cyclopenten-1-ones and their stereoselective transformation to 5-(2-acetoxyethylidene)-2-cyclopenten-1-ones

  摘要：

  DOI：

  10.1021/jo00302a027
• 作为产物：
  描述：

  1,1-Dimethoxy-1,2-dihydro-5,7-dioxa-cyclobuta[e]indene 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 25.0h， 生成 5,6-(methylenedioxy)benzocyclobutenone
  参考文献：
  名称：

  Synthesis of substituted benzocyclobutenediones

  摘要：

  DOI：

  10.1021/jo00267a037

文献信息

• Thermal <i>Hetero</i>-Diels–Alder Reaction of Benzocyclobutenones with Isatins To Form 2-Oxindole Spirolactones
  作者：Thomas Wurm、Ben W. H. Turnbull、Brett R. Ambler、Michael J. Krische

  DOI：10.1021/acs.joc.7b02769

  日期：2017.12.15

  or “ortho-quinoid ketene methides”, which engage in intermolecular [4+2] cycloadditions with isatins 2a–2f to form 2-oxindole spirolactones 3a–3l. This process tolerates an array of different functional groups and substitution patterns, and is applicable to unprotected isatins 2b–2f bearing free NH-functionalities. The superior performance of isatins compared to other carbonyl based dienophiles was

  苯并环丁烯酮1a – 1g在间二甲苯溶剂中于 150 °C 下发生环化，形成瞬态 α-氧代-邻醌二甲烷或“邻醌烯酮甲基化物”，其与靛红2a – 2f进行分子间 [4+2] 环加成，生成形成 2-羟吲哚螺内酯3a – 3l 。该过程可耐受一系列不同的官能团和取代模式，并且适用于带有游离 NH 官能团的未受保护的靛红2b – 2f 。与其他基于羰基的亲二烯体相比，靛红的优越性能通过量子化学计算得到了证明和合理化。
• Synthesis of metallacyclopentenones by insertion of rhodium into cyclobutenones
  作者：Mark A. Huffman、Lanny S. Liebeskind、William T. Pennington

  DOI：10.1021/om00158a009

  日期：1990.8
• Huffman, Mark A.; Liebeskind, Lanny S.; Pennington, William T., Organometallics, 1992, vol. 11, # 1, p. 255 - 266
  作者：Huffman, Mark A.、Liebeskind, Lanny S.、Pennington, William T.

  DOI：——

  日期：——
• Rapid, convergent, and regioselective synthesis of anthracenes
  作者：John J. Fitzgerald、Neville E. Drysdale、R. A. Olofson

  DOI：10.1021/jo00052a027

  日期：1992.12

  Anthracenes are obtained in moderate to good yield by the simultaneous treatment of benzocyclobutenols and halobenzenes with LTMP in tetrahydropyran. In the key step of this one-pot process, o-toluoyl anion intermediates from the known ring-opening of benzocyclobutenoxides add to halobenzene derived arynes. Methoxy-substituted benzocyclobutenols which are readily made regiospecifically by known methods also react regiospecifically with the single benzyne generated from either a 2- or 3-haloanisole. For example, the only trimethoxyanthracene isolated (48% yield) from the reaction of 6-methoxybenzocyclobutenol (8) with 5-chloro-1,3-dimethoxybenzene is the 1,3,8-isomer 20. When 1,2-dihydrocyclobuta[l]phenanthren-1-ol (14) and/or halonaphthalenes are the reactants, benzannulated anthracenes are formed; e.g., tribenz[a,c,h]anthracene in 68% yield from 14 and bromonaphthalene. In another extension, pentaphene (31) was made in one pot from o-dichlorobenzene.
• STONE, GUY B.;LIEBESKIND, LANNY S., J. ORG. CHEM., 55,(1990) N5, C. 4614-4622
  作者：STONE, GUY B.、LIEBESKIND, LANNY S.

  DOI：——

  日期：——