tris(4-dimethylamino phenyl)boroxine | 107176-00-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: tris(4-dimethylamino phenyl)boroxine
• 英文别名: Tris-(4-dimethylamino-phenyl)-boroxin；4-[4,6-bis[4-(dimethylamino)phenyl]-1,3,5,2,4,6-trioxatriborinan-2-yl]-N,N-dimethylaniline
• CAS: 107176-00-1
• 化学式: C₂₄H₃₀B₃N₃O₃
• 分子量: 440.954
• InChiKey: SWJAGLLWSGUJIF-UHFFFAOYSA-N

物化性质

• 沸点：
  523.8±60.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.43
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  碘化氰 、 tris(4-dimethylamino phenyl)boroxine 在 (CuOTf)*toluene 、 cesium fluoride 、 4,4'-二叔丁基-2,2'-二吡啶 作用下， 以 甲醇 、 水 为溶剂， 反应 12.0h， 以64%的产率得到4-(二甲胺基)苄腈
  参考文献：
  名称：

  Copper-Catalyzed Cyanation of Aryl- and Alkenylboronic Reagents with Cyanogen Iodide

  摘要：

  Direct catalytic cyanation of organoboronic acids with cyanogen iodide has been achieved by using a copper bipyridine catalyst system. The cyanation reaction is likely to occur through two catalytic cycles: copper(II)-catalyzed iodination of organoboronic acids and the following cyanidocopper(I)-mediated cyanation of organic iodides.

  DOI：

  10.1021/acs.orglett.5b01924
• 作为产物：
  描述：

  [4-(dimethylamino)phenyl]-[di(propan-2-yl)amino]boron 在 水 作用下， 反应 16.0h， 生成 tris(4-dimethylamino phenyl)boroxine
  参考文献：
  名称：

  Improved transparency–nonlinearity trade-off with boroxine-based octupolar molecules

  摘要：

  一系列源自硼环结构的八极分子被设计，并通过在溶液中进行谐波光散射实验来研究其光学非线性特性；结果发现，这些分子在近紫外-可见区域（λmax ≤ 280 nm）具有优良的透明度，并且显著的一级超极化率（高达β(0) = 56 × 10⁻³⁰ esu）。

  DOI：

  10.1039/b308664j

文献信息

• Mutual Activation: Suzuki-Miyaura Coupling through Direct Cleavage of the sp2 CO Bond of Naphtholate
  作者：Da-Gang Yu、Zhang-Jie Shi

  DOI：10.1002/anie.201101461

  日期：2011.7.25

  Working together: A new approach of mutual activation between naphtholates and aryl boronic acid derivatives by the formation of borates to facilitate the Suzuki–Miyaura coupling through direct cleavage of the sp2 CO bond by nickel catalysis is described (see scheme; R′: annulated ring system). Various naphtholates and aryl boronic acid derivatives could be directly coupled in good yields.

  一起工作：由硼酸盐的形成相互活化的naphtholates和芳基硼酸衍生物之间的一种新方法，以促进通过SP的直接裂解铃木-宫浦偶合2 ç  Ò由镍催化键被描述（参见方案; R' ：环形环系统）。各种萘甲酸酯和芳基硼酸衍生物可以以良好的产率直接偶联。
• Torssell, Arkiv foer Kemi, 1957, vol. 10, p. 507,509
  作者：Torssell

  DOI：——

  日期：——
• Enantiospecific, Nickel-Catalyzed Cross-Couplings of Allylic Pivalates and Arylboroxines
  作者：Harathi D. Srinivas、Qi Zhou、Mary P. Watson

  DOI：10.1021/ol5016724

  日期：2014.7.3

  We have developed an enantiospecific, nickel-catalyzed cross-coupling of unsymmetric 1,3-disubstituted allylic pivalates with arylboroxines. The success of this reaction relies on the use of BnPPh2 as a supporting ligand for the nickel(0) catalyst and NaOMe as a base. This method shows excellent functional group tolerance and broad scope in both the allylic pivalate and arylboroxine, enabling the preparation of 1,3-diaryl allylic products in high yields with excellent levels of regioselectivity and stereochemical fidelity.
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: B: B-Verb.13, 4.7.2.6, page 219 - 226
  作者：

  DOI：——

  日期：——
• Stereospecific, Nickel-Catalyzed Suzuki–Miyaura Cross-Coupling of Allylic Pivalates To Deliver Quaternary Stereocenters
  作者：Kelsey M. Cobb、Javon M. Rabb-Lynch、Megan E. Hoerrner、Alex Manders、Qi Zhou、Mary P. Watson

  DOI：10.1021/acs.orglett.7b02063

  日期：2017.8.18

  Recognizing the importance of all-carbon, quaternary stereocenters in complex molecule synthesis, a stereospecific, nickel-catalyzed cross-coupling of allylic pivalates with arylboroxines to deliver products equipped with quaternary stereocenters and internal alkenes was developed. The enantioenriched allylic pivalate starting materials are readily prepared, and a variety of functional groups can be incorporated on both the allylic pivalate and the arylboroxine. Additional advantages include the use of a commercially available and air-stable Ni(II) salt and BISBI ligand, mild reaction conditions, and high yields and ee's. The observed stereoinversion of this reaction is consistent with an open transition state in the oxidative addition step.