2,4,6-tris(3-acetylphenyl)boroxine | 1313872-77-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,4,6-tris(3-acetylphenyl)boroxine
• 英文别名: 3-acetylphenylboroxine
• CAS: 1313872-77-3
• 化学式: C₂₄H₂₁B₃O₆
• 分子量: 437.86
• InChiKey: CJFQWXAHSZWQII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.84
• 重原子数：
  33.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  78.9
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2,4,6-tris(3-acetylphenyl)boroxine 、 (R)-4-phenylbutan-2-yl pivalate 在 bis(1,5-cyclooctadiene)nickel (0) 、 sodium methylate 、 苄基二苯膦 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以86%的产率得到(S,E)-1-(3-(4-phenylbut-3-en-2-yl)phenyl)ethanone
  参考文献：
  名称：

  Enantiospecific, Nickel-Catalyzed Cross-Couplings of Allylic Pivalates and Arylboroxines

  摘要：

  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.

  DOI：

  10.1021/ol5016724
• 作为产物：
  描述：

  3-乙酰基苯硼酸 120.0 ℃ 、10.0 Pa 条件下， 生成 2,4,6-tris(3-acetylphenyl)boroxine
  参考文献：
  名称：

  钯（II）催化的α-（三氟甲基）芳基甲胺的对映选择性合成

  摘要：

  我们描述了一种合成α-（三氟甲基）芳基甲胺的方法，该方法由钯（II）催化将芳基硼氧烷加成到衍生自三氟乙醛的亚胺上。乙酸钯用作具有电子中性或电子富集的芳基硼氧烷的催化剂，并且发现添加铵盐或银盐对于促进贫电子的硼氧烷的反应至关重要。以（S）-t -Bu-PyOX为手性配体，该方法以57-91％的产率提供了多种α-三氟甲基化胺，在大多数情况下，ee大于92％。

  DOI：

  10.1021/acs.joc.6b00657

文献信息

• Highly Functional Group Compatible Rh-Catalyzed Addition of Arylboroxines to Activated <i>N</i>-<i>tert</i>-Butanesulfinyl Ketimines
  作者：Hyung Hoon Jung、Andrew W. Buesking、Jonathan A. Ellman

  DOI：10.1021/ol201438k

  日期：2011.8.5

  The rhodium-catalyzed addition of readily accessible arylboroxines to N-tert-butanesulfinyl ketimines derived from oxetan-3-one, N-Boc-azetidin-3-one, and isatins proceeds In high yields with excellent functional group compatibility. Moreover, high diastereoselectivities are observed for the additions to the N-sulfinyl ketimines derived from isatins.
• Rh-Catalyzed Addition of Arylboroxines to Cyclic <i>N</i>-(Isopropanesulfinyl)ketimines
  作者：Hyung Hoon Jung、Andrew W. Buesking、Jonathan A. Ellman

  DOI：10.1021/jo301634y

  日期：2012.11.2

  Arylboroxines, which are easily accessed by drying commercially available arylboronic acids, are added to N-(isopropanesulfinyl)ketimines derived from cyclohexanone, N-Boc-piperidin-4-one, and tetrahydropyran-4-one in high yields and with excellent functional group compatibility via rhodium catalysis. These results contrast with additions to the corresponding ketimines incorporating the larger N-tert-butanesulfinyl group, which give considerably lower yields. Efficient two-step preparation of racemic isopropanesulfinamide from inexpensive isopropyl disulfide and recycling of the isopropanesulfinyl group from the addition products are also described.
• Rhodium-Catalyzed Asymmetric Hydroarylation of 3-Pyrrolines Giving 3-Arylpyrrolidines: Protonation as a Key Step
  作者：Chau Ming So、Satoshi Kume、Tamio Hayashi

  DOI：10.1021/ja406169s

  日期：2013.7.31

  A hydroxorhodium complex coordinated with (R)-segphos was found to catalyze the hydroarylation of 3-pyrrolines with arylboroxines under neutral conditions to give 3-arylpyrrolidines with high enantioselectivity in high yields.