di(1'-naphthyl)borinic acid | 62981-91-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: di(1'-naphthyl)borinic acid
• 英文别名: Dinaphthalen-1-ylborinic acid
• CAS: 62981-91-3
• 化学式: C₂₀H₁₅BO
• 分子量: 282.149
• InChiKey: JZZJOBIELUXIGQ-UHFFFAOYSA-N

物化性质

• 熔点：
  105-106 °C
• 沸点：
  500.9±33.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.09
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  di(1'-naphthyl)borinic acid 在 盐酸 作用下， 生成 (β-amino-isobutoxy)-di-[1]naphthyl-borane
  参考文献：
  名称：

  Organoboron Compounds. V. The Preparation of an Unsymmetrical Diarylborinate

  摘要：

  DOI：

  10.1021/ja01614a038
• 作为产物：
  描述：

  Tri-naphthalen-1-yl-borane 以 乙醚 为溶剂， 生成 di(1'-naphthyl)borinic acid
  参考文献：
  名称：

  Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: B: B-Verb.8, 11.3.10, page 213 - 216

  摘要：

  DOI：

文献信息

• Highly efficient synthesis of aryl ketones by PEPPSI-palladium catalyzed acylative Suzuki coupling of amides with diarylborinic acids
  作者：Chen Wang、Lingyun Huang、Fengze Wang、Gang Zou

  DOI：10.1016/j.tetlet.2018.05.003

  日期：2018.6

  An improved acylative cross-coupling of various N-methyl-N-tosyl amides with diarylborinic acids for synthesis of aryl ketones is developed. In most cases, aryl ketones could be obtained in excellent yields by using 1 mol% 2,6-diisopropylphenylimidazolylidene and 3-chloropyridine co-supported palladium chloride as catalyst in the presence of 3 equiv. K2CO3 as base in refluxing THF. The readily prepared

  已开发了用于合成芳基酮的各种N-甲基-N-甲苯磺酰基酰胺与二芳基硼酸的改进的酰基交叉偶联。在大多数情况下，在3当量的存在下，通过使用1mol％的2,6-二异丙基苯基咪唑基亚甲基和3-氯吡啶共负载的氯化钯作为催化剂，可以以优异的产率获得芳基酮。在回流的THF中，以K 2 CO 3为碱。容易制备且具有成本效益的底物，N-甲基-N-甲苯磺酰胺和二芳基硼酸，以及可商购的催化剂体系，保证了实用和有效地获得芳基酮。
• Nitrones and oximes of bifunctional carbonyl compounds and their reaction products with diarylborinic acids. Crystal and molecular structure of examples of five-, six-, and seven-membered boron chelates
  作者：Wolfgang Kliegel、Gottfried Lubkowitz、Jens O Pokriefke、Steven J Rettig、James Trotter

  DOI：10.1139/v00-137

  日期：2000.10.1

  Synthesis has been carried out of diarylboron chelates of 2- and 3-hydroxynitrones, of 2- and 3-hydroxyoximes, and of 2-carboxynitrones and a 2-carboxyoxime. The structures have been determined from spectroscopic data and from X-ray analyses of 5d, 9a, 11b, and 19. Crystals (at 180 K) of 5d are monoclinic, a = 10.543(2), b = 19.085(4), c = 10.2667(3) Å, β = 90.4978(7)°, Z = 4, space group P2₁/c; those of 9a are orthorhombic, a = 10.9913(5), b = 14.9329(7), c = 10.2460(13) Å, Z = 4, space group P2₁2₁2₁; those of 11b are monoclinic, a = 11.227(2), b = 9.967(2), c = 17.0537(4) Å, β = 105.4179(5)°, Z = 4, space group P2₁/n; those of 19 are monoclinic, a = 11.1847(15), b = 13.715(3), c = 11.5559(5) Å, β = 104.8730(10)°, Z = 4, space group P2₁/n. The structures were solved by direct methods and refined by full-matrix least-squares procedures to R(F, I [Formula: see text] 3σ(I)) = 0.049, 0.047, 0.042, and 0.047, respectively, for CCD data for 5d, 9a, 11b, and 19. The four molecules contain five-, seven-, six-, and five-membered rings, respectively, with O-B-N groups in the 5d, 11b, and 19, and O-B-O in 9a; the rings exhibit various deviations from planarity, particularly the seven-membered ring.Key words: diarylboron chelates, hydroxyoximes, hydroxynitrones, carboxyoximes, carboxynitrones, organoboron compounds, crystal structure.

  已合成2-和3-羟基亚硝基酮的二芳基硼螯合物，2-和3-羟基肟的二芳基硼螯合物，以及2-羧基亚硝基酮和2-羧基肟。这些结构是通过光谱数据和对5d、9a、11b和19的X射线分析确定的。5d的晶体（在180K）为单斜晶系，a = 10.543(2) Å，b = 19.085(4) Å，c = 10.2667(3) Å，β = 90.4978(7)°，Z = 4，空间群P21/c；9a的晶体为正交晶系，a = 10.9913(5) Å，b = 14.9329(7) Å，c = 10.2460(13) Å，Z = 4，空间群P212121；11b的晶体为单斜晶系，a = 11.227(2) Å，b = 9.967(2) Å，c = 17.0537(4) Å，β = 105.4179(5)°，Z = 4，空间群P21/n；19的晶体为单斜晶系，a = 11.1847(15) Å，b = 13.715(3) Å，c = 11.5559(5) Å，β = 104.8730(10)°，Z = 4，空间群P21/n。这些结构是通过直接方法解决的，并通过全矩阵最小二乘法进行了精细化处理，对于5d、9a、11b和19的CCD数据，分别为R(F, I [Formula: see text] 3σ(I)) = 0.049、0.047、0.042和0.047。这四种分子分别包含五、七、六和五元环，其中5d、11b和19含有O-B-N基团，9a含有O-B-O基团；这些环体现出各种与平面性的偏差，特别是七元环。关键词：二芳基硼螯合物、羟基肟、羟基亚硝基酮、羧基肟、羧基亚硝基酮、有机硼化合物、晶体结构。
• Absolute stereochemical determination of 1,2‐diols via complexation with dinaphthyl borinic acid
  作者：Saeedeh Torabi Kohlbouni、Aritra Sarkar、Jun Zhang、Xiaoyong Li、Babak Borhan

  DOI：10.1002/chir.23223

  日期：2020.6

  Rapid derivatization of chiral 1,2‐diols with dinaphthyl borinic acid (DBA) leads to a cyclic boronate, enabling the absolute stereochemical prediction via exciton‐coupled circular dichroic (ECCD) of the naphthyl groups. Aryl‐ and alkyl‐substituted 1,2‐diols derivatized with DBA yield a predictable ECCD, which is also in agreement with theoretical predictions derived from computationally minimized

  手性1,2-二醇与二萘基硼酸（DBA）的快速衍生化生成环状硼酸酯，从而可以通过对萘基的激子偶联圆二色性（ECCD）进行绝对立体化学预测。用DBA衍生的芳基和烷基取代的1,2-二醇可产生可预测的ECCD，这也与从计算最小化结构得出的理论预测相符。
• New Boron-Containing Molybdenum Imido Alkylidene Complexes for Linear Olefin Homometathesis
  作者：Alexandre Nasr、Pierre-Alain R. Breuil、Duarte C. Silva、Mikaël Berthod、Nicolas Dellus、Erwann Jeanneau、Marc Lemaire、Hélène Olivier-Bourbigou

  DOI：10.1021/om400577k

  日期：2013.10.14

  X-ray diffraction, and elemental analysis. Complex 1 proved to be active for homometathesis reactions of 1- and 2-octene at 0.1 mol % loading. The synthesis of mixed pyrrolide boroxide imido molybdenum alkylidene complexes was extended to other borinic acids. The catalytic activity of these new complexes was evaluated in the homometathesis of linear olefins.

  新的钼亚氨基亚烷基络合物Mo（N（2,6- i Pr 2 C 6 H 3））（CHCMe 2 Ph）（NC 4 H 2 Me 2）（OB（Mes）2）（1 ; Mes = 2，据报道同时含有硼氧化物和吡咯化物配体的4，6-MePh）。它的形成是由于双（甲磺酰基）硼酸（（Mes）2 BOH）与双吡咯化物Schrock型前体Mo（N-2,6- i Pr 2 C 6 H 3）（CHCMe 2 Ph）之间的反应（NC 4 H 2我2）2。该复合物通过1 H，13 C，11 B和95 Mo NMR光谱，X射线衍射和元素分析充分表征。事实证明，配合物1在0.1摩尔％的负载下对1-和2-辛烯的复分解反应具有活性。混合的吡咯化物硼氧化物亚氨基酰亚胺钼亚烷基络合物的合成扩展到其他硼酸。这些新的配合物的催化活性在线性烯烃的均复分解中进行了评估。
• Boron photochemistry III. Photolysis of some naphthalene-substituted borate complexes
  作者：J.L.R. Williams、P.J. Grisdale、J.C. Doty、M.E. Glogowski、B.E. Babb、D.P. Maier

  DOI：10.1016/s0022-328x(00)92638-x

  日期：1968.9

  The photolysis of two naphthalene-substituted “ate” complexes, lithium tetra-2-naphthylborate and lithium phenyltri-1-naphthylborate, has been carried out in the presence and absence of air. In both cases in the absence of air, the products are dihydrobiaryls, biaryls and diarylborinic acids. Air eliminates the dihydro derivatives to provide the biaryls and naphthols which result at the expense of

  两种萘取代的“酸酯”络合物，四-2-萘基硼酸锂和苯基三-1-萘基硼酸锂的光解是在有空气和没有空气的条件下进行的。在没有空气的两种情况下，产物都是二氢联芳基，联芳基和二芳基硼酸。空气消除了二氢衍生物，从而提供了联芳基和萘酚，其结果是以牺牲二芳基硼酸为代价的。苯基三-1-萘基硼酸锂的光解产物中不存在联苯和苯基环己二烯，表明该光解是分子内的。