5,5-Dimethyl-2-(7-phenyl-1,3-dihydro-2-benzofuran-4-yl)-1,3,2-dioxaborinane | 892869-30-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: 5,5-Dimethyl-2-(7-phenyl-1,3-dihydro-2-benzofuran-4-yl)-1,3,2-dioxaborinane
• 英文别名: 5,5-dimethyl-2-(7-phenyl-1,3-dihydro-2-benzofuran-4-yl)-1,3,2-dioxaborinane
• CAS: 892869-30-6
• 化学式: C₁₉H₂₁BO₃
• 分子量: 308.185
• InChiKey: BUKPSSQHSJAQKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.15
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,7-Diiodo-2',2'-dimethylspiro[1,3-dihydroindene-2,5'-1,3-dioxane] 、 5,5-Dimethyl-2-(7-phenyl-1,3-dihydro-2-benzofuran-4-yl)-1,3,2-dioxaborinane 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 2-双环己基膦-2',6'-二甲氧基联苯 、 potassium phosphate 作用下， 以 甲苯 为溶剂， 反应 15.0h， 以50%的产率得到
  参考文献：
  名称：

  Synthesis of Bicyclic p-Diiodobenzenes via Silver-Catalyzed Csp-H Iodination and Ruthenium-Catalyzed Cycloaddition

  摘要：

  Highly substituted iodobenzenes were efficiently and regioselectively synthesized from readily available 1,6-diynes via two-step process consisting of silver-catalyzed Csp-H iodination and subsequent ruthenium-catalyzed [2+2+2] cycloaddition of resultant iododiynes. Some of the obtained iodobenzenes were subjected to palladium-catalyzed C-C bond-forming reactions such as Mizoroki-Heck reaction, Sonogashira reaction, and Suzuki-Miyaura coupling, giving highly conjugated molecules.

  DOI：

  10.1021/ja061619p
• 作为产物：
  描述：

  5,5-Dimethyl-2-[3-(3-phenylprop-2-ynoxy)prop-1-ynyl]-1,3,2-dioxaborinane 、 乙炔 在 chloro(1,5-cyclooctadiene)(pentamethylcyclopentadiene)ruthenium(II) 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.0h， 以73%的产率得到5,5-Dimethyl-2-(7-phenyl-1,3-dihydro-2-benzofuran-4-yl)-1,3,2-dioxaborinane
  参考文献：
  名称：

  Synthesis of arylboronates via Cp*RuCl-catalyzed cycloaddition of alkynylboronates

  摘要：

  In the presence of 5-10 mol% Cp*RuCI(cod), 1,6- and 1,7-diynes were allowed to react with an ethynylboronate at ambient temperature to give rise to bicyclic arylboronates in 64-93% isolated yields. 1,6-Diynes bearing a boronate terminal also underwent cycloaddition with monoalkynes to give the corresponding bicyclic arylboronates. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.02.068

文献信息

• Synthesis of arylboronates via Cp*RuCl-catalyzed cycloaddition of alkynylboronates
  作者：Yoshihiko Yamamoto、Kozo Hattori、Jun-ichi Ishii、Hisao Nishiyama

  DOI：10.1016/j.tet.2006.02.068

  日期：2006.5

  In the presence of 5-10 mol% Cp*RuCI(cod), 1,6- and 1,7-diynes were allowed to react with an ethynylboronate at ambient temperature to give rise to bicyclic arylboronates in 64-93% isolated yields. 1,6-Diynes bearing a boronate terminal also underwent cycloaddition with monoalkynes to give the corresponding bicyclic arylboronates. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis of Bicyclic <i>p</i>-Diiodobenzenes via Silver-Catalyzed C<i>sp</i>-H Iodination and Ruthenium-Catalyzed Cycloaddition
  作者：Yoshihiko Yamamoto、Kozo Hattori、Hisao Nishiyama

  DOI：10.1021/ja061619p

  日期：2006.6.1

  Highly substituted iodobenzenes were efficiently and regioselectively synthesized from readily available 1,6-diynes via two-step process consisting of silver-catalyzed Csp-H iodination and subsequent ruthenium-catalyzed [2+2+2] cycloaddition of resultant iododiynes. Some of the obtained iodobenzenes were subjected to palladium-catalyzed C-C bond-forming reactions such as Mizoroki-Heck reaction, Sonogashira reaction, and Suzuki-Miyaura coupling, giving highly conjugated molecules.