4,4,5,5-tetramethyl-2-(1-phenyl-3,4-nonadien-5-yl)-[1,3,2]dioxaborolane | 1082069-29-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4,4,5,5-tetramethyl-2-(1-phenyl-3,4-nonadien-5-yl)-[1,3,2]dioxaborolane
• 英文别名: 4,4,5,5-tetramethyl-2-(1-phenylnona-3,4-dien-5-yl)-1,3,2-dioxaborolane；PhCH2CH2CHCC(Bu)B(pinacolato)；PhCH2CH2CHCC(Bu)B(pin)
• CAS: 1082069-29-1
• 化学式: C₂₁H₃₁BO₂
• 分子量: 326.287
• InChiKey: FGTVPZJBXAQJEM-QGZVFWFLSA-N

物化性质

• 沸点：
  394.8±45.0 °C(Predicted)
• 密度：
  0.94±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.52
• 重原子数：
  24.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  碘苯 、 4,4,5,5-tetramethyl-2-(1-phenyl-3,4-nonadien-5-yl)-[1,3,2]dioxaborolane 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium carbonate 、 copper(l) chloride 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 16.0h， 以18%的产率得到nona-3,4-diene-1,5-diyldibenzene
  参考文献：
  名称：

  Synthesis of Allenes by Catalytic Coupling of Propargyl Carbonates with Aryl Iodides in the Presence of Diboron Species

  摘要：

  Bimetallic copper-/palladium-catalyzed multicomponent reaction of propargyl carbonates, aryl iodides, and diboron species was studied. This procedure can be used for synthesis of di-, tri-, and tetra-substituted allenes. Using diboronic acid, the reaction is supposed to proceed via allenylboronic acid intermediate.

  DOI：

  10.1021/acs.joc.5b01842
• 作为产物：
  描述：

  苯丙醛 在 吡啶 、 copper(l) iodide 、 四(三苯基膦)钯 、 正丁基锂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 18.67h， 生成 4,4,5,5-tetramethyl-2-(1-phenyl-3,4-nonadien-5-yl)-[1,3,2]dioxaborolane
  参考文献：
  名称：

  Borylation of Propargylic Substrates by Bimetallic Catalysis. Synthesis of Allenyl, Propargylic, and Butadienyl Bpin Derivatives

  摘要：

  Bimetallic Pd/Cu and Pd/Ag catalytic systems were used for borylation of propargylic alcohol derivatives. The substrate scope includes even terminal alkynes. The reactions proceed stererospecifically with formal S(N)2' pathways to give allenyl boronates. Opening of propargyl epoxides leads to 1,2-diborylated butadienes probably via en allenylboronate intermediate.

  DOI：

  10.1021/ja502792s

文献信息

• Practical Synthesis of Allyl, Allenyl, and Benzyl Boronates through S_N1′-Type Borylation under Heterogeneous Gold Catalysis
  作者：Hiroki Miura、Yuka Hachiya、Hidenori Nishio、Yohei Fukuta、Tomoya Toyomasu、Kosa Kobayashi、Yosuke Masaki、Tetsuya Shishido

  DOI：10.1021/acscatal.0c03771

  日期：2021.1.15

  Efficient borylation of sp3 C–O bonds by supported Au catalysts is described. Au nanoparticles supported on TiO2 showed high activity under mild conditions employing low catalyst loading conditions without the aid of any additives, such as phosphine and bases. A variety of allyl, propargyl, and benzyl substrates participated in the heterogeneously catalyzed reactions to furnish the corresponding allyl

  描述了负载型Au催化剂对sp 3 C–O键的有效硼化作用。负载在TiO 2上的Au纳米颗粒在温和条件下采用低催化剂负载条件显示出高活性，而无需任何添加剂，例如膦和碱。各种烯丙基，炔丙基和苄基底物参与了非均相催化反应，以高产率提供了相应的烯丙基，烯丙基和苄基硼酸酯。此外，Au / TiO 2对烯丙基和苄基醇的直接硼化也有效。基于Hammett研究和控制实验的机理研究表明，负载型Au催化剂上的sp 3 C–O键硼化通过S N进行1'型机制涉及碳阳离子中间体的形成。负载的金催化剂的高活性，可重复使用性和环境相容性以及反应体系的可扩展性使有价值的有机硼化合物的实际合成成为可能。
• Copper(I)-Catalyzed Substitution of Propargylic Carbonates with Diboron: Selective Synthesis of Multisubstituted Allenylboronates
  作者：Hajime Ito、Yusuke Sasaki、Masaya Sawamura

  DOI：10.1021/ja806602h

  日期：2008.11.26

  A versatile synthetic method for the preparation of the allenylboronates, Cu(I)-catalyzed reaction of propargylic carbonates with a diboron, is described. A Cu(O-t-Bu)-Xantphos catalyst system was effective for the preparation of various allenylboron compounds, allenylboronates with different substitution patterns, those with functional groups, and an axially chiral one. The Lewis acid promoted stereoselective addition to aldehydes leading to homopropargylic alcohols showed the usefulness of the new allenylboronates.