5-甲氧基-7-甲基二环[4.2.0]辛-1,3,5-三烯-7-醇 | 681478-55-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 5-甲氧基-7-甲基二环[4.2.0]辛-1,3,5-三烯-7-醇
• 英文名称: 6-methoxy-1-methyl-1,2-dihydrocyclobutabenzen-1-ol
• 英文别名: benzocyclobutenol；5-methoxy-7-methylbicyclo[4.2.0]octa-1,3,5-trien-7-ol；5-Methoxy-7-methylbicyclo[4.2.0]octa-1(6),2,4-trien-7-ol
• CAS: 681478-55-7
• 化学式: C₁₀H₁₂O₂
• 分子量: 164.204
• InChiKey: FJTNDUJCXCXAIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-甲氧基-7-甲基二环[4.2.0]辛-1,3,5-三烯-7-醇 在 tris-(dibenzylideneacetone)dipalladium(0) 、 对苄基三氟甲磺酸 、 caesium carbonate 、 2-二环己膦基-2'-(N,N-二甲胺)-联苯 作用下， 以 甲苯 为溶剂， 以82%的产率得到3-甲氧基苯基丙酮
  参考文献：
  名称：

  Palladium-Catalyzed Selective Carboelimination and Cross-Coupling Reactions of Benzocyclobutenols with Aryl Bromides

  摘要：

  The palladium-catalyzed selective beta-carboelimination and cross-coupling chemistry of benzocyclobutenols is described. In contrast to the base-mediated ring-opening reactions of benzocyclobutenols, this variant proceeds with exclusive cleavage of the proximal bond.

  DOI：

  10.1021/jo201632c

文献信息

• Expeditious Synthesis of Isoquinolone Derivatives by Rhodium(I)-Catalyzed Annulation Reaction through C–C Bond Cleavage
  作者：Yiyi He、Chengsha Yuan、Zeqi Jiang、Li Shuai、Qing Xiao

  DOI：10.1021/acs.orglett.8b03653

  日期：2019.1.4

  A Rh(I)-catalyzed intermolecular cyclization between isocyanates and benzocyclobutenols leading to isoquinolin-1(2H)-ones through selective cleavage of a C–C bond has been realized. Exploiting the same strategy, we developed a Rh(I)-catalyzed three-component reaction of benzocyclobutenols, isonitriles, and sulfonyl azides to access isoquinolin-1(2H)-imines. These procedures provide unique and expeditious

  通过选择性裂解CC键，Rh（I）催化的异氰酸酯和苯并环丁烯醇之间的分子间环化反应导致异喹啉-1（2 H）-ones的形成。利用相同的策略，我们开发了Rh（I）催化的苯并环丁烯醇，异腈和磺酰叠氮化物的三组分反应，以访问异喹啉-1（2 H）-亚胺。这些程序提供了异喹诺酮衍生物的独特而迅速的途径，否则在温和的反应条件下，很难以令人满意的产率制备具有优异的官能团耐受性的异喹诺酮衍生物。
• Pd-Catalyzed Ring-Closing/Ring-Opening Cross Coupling Reactions: Enantioselective Diarylation of Unactivated Olefins
  作者：Lantao Liu、Fangyuan Cheng、Chenxiang Meng、An-An Zhang、Mingliang Zhang、Kai Xu、Naoki Ishida、Masahiro Murakami

  DOI：10.1021/acscatal.1c02277

  日期：2021.7.16

  Pd-catalyzed chemo-, regio-, and enantioselective ring-closing/ring-opening cross coupling reaction has been developed with diverse aryl halide-tethered alkenes and benzocyclobutenols as substrates, which renders the highly enantioselective diarylation of unactivated alkenes and provides a convenient method toward chiral 2,3-dihydrobenzofurans bearing a quaternary stereocenter with excellent enantioselectivities

  Pd催化的化学-、区域-和对映选择性闭环/开环交叉偶联反应已经开发出来，以多种芳基卤化物系链烯烃和苯并环丁烯醇为​​底物，这使得未活化烯烃的高度对映选择性二芳基化并提供了一种方便的方法具有四元立体中心的手性 2,3-二氢苯并呋喃，具有出色的对映选择性（高达 98% ee）。描述了大麻素受体2激动剂类似物在简明合成中的应用。
• Formal Carbene Insertion into C–C Bond: Rh(I)-Catalyzed Reaction of Benzocyclobutenols with Diazoesters
  作者：Ying Xia、Zhenxing Liu、Zhen Liu、Rui Ge、Fei Ye、Mohammad Hossain、Yan Zhang、Jianbo Wang

  DOI：10.1021/ja500118w

  日期：2014.2.26

  formal carbene insertion into C-C bond of benzocyclobutenols has been realized by employing diazoesters as carbene precursors. The product indanol derivatives were obtained in good yields and in diastereoselective manner under mild reaction conditions. All-carbon quaternary center is constructed at the carbenic carbon. This catalytic reaction involves selective cleavage of C-C bond, Rh(I) carbene insertion

  已经通过使用重氮酯作为卡宾前体实现了 Rh(I) 催化的形式卡宾插入苯并环丁烯醇的 CC 键。在温和的反应条件下，以良好的收率和非对映选择性的方式获得了产物茚满醇衍生物。全碳四元中心是在碳碳上构建的。该催化反应涉及 CC 键的选择性裂解、Rh(I) 卡宾插入和分子内醛醇反应。
• A palladium-catalyzed sequential Heck coupling/C–C bond activation approach to oxindoles with all-carbon-quaternary centers
  作者：Guoliang Mao、Chenxiang Meng、Fangyuan Cheng、Wenbo Wu、Yuan-Yuan Gao、Gao-Wei Li、Lantao Liu

  DOI：10.1039/d1ob02440j

  日期：——

  Catalytic construction of oxindoles bearing all-carbon-quaternary centers attracts wide attention from the synthetic chemistry community. Herein, we report a palladium-catalyzed sequential Heck coupling/C–C bond activation of aryl halide-tethered alkenes with benzocyclobutenols affording a series of oxindole-derived compounds in good to excellent yields, as well as the preliminary enantioselectivity

  全碳四元中心羟基吲哚的催化构建引起了合成化学界的广泛关注。在此，我们报告了钯催化的芳基卤化物系链烯烃与苯并环丁烯醇的顺序 Heck 偶联/C-C 键活化，以良好至优异的产率提供了一系列羟吲哚衍生化合物，以及初步的对映选择性结果。