hydroxy-[1]naphthyl-phenyl-borane | 13331-25-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: hydroxy-[1]naphthyl-phenyl-borane
• 英文别名: [1]Naphthyl-phenyl-borinsaeure；Hydroxy-[1]naphthyl-phenyl-boran；Naphthalen-1-yl(phenyl)borinic acid
• CAS: 13331-25-4
• 化学式: C₁₆H₁₃BO
• 分子量: 232.09
• InChiKey: MXLUZENZSFGANK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.94
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• 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：

  hydroxy-[1]naphthyl-phenyl-borane 在 盐酸 作用下， 生成 (β-amino-isobutoxy)-[1]naphthyl-phenyl-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：

  diisobutyl phenylborate 在 sodium hydroxide 、 五氯化磷 作用下， 生成 hydroxy-[1]naphthyl-phenyl-borane
  参考文献：
  名称：

  Michailow; Fedotow, Zhurnal Obshchei Khimii, 1959, vol. 29, p. 2244,2247; engl. Ausg. S. 2210, 2213

  摘要：

  DOI：

文献信息

• Formation of heterocyclic arylboronates by thermally induced 1,4-aryl migration in diarylboron chelates of <i>C</i>-(1-hydro×yalkyl)nitrones. Crystal and molecular structures of some of the rearrangement products and of one of the educts
  作者：Wolfgang Kliegel、Gottfried Lubkowitz、Jens O. Pokriefke、Steven J. Rettig、James Trotter

  DOI：10.1139/cjc-79-2-226

  日期：——

  Synthesis of heterocyclic arylboronates has been carried out by thermally induced rearrangement of diarylboron chelates of C-(1-hydroxyalkyl)nitrones. The structures have been determined from spectroscopic data and from X-ray analyses. Thermoanalytical and time-dependent NMR measurements give information on the nature of the isomerization reaction. Crystal data (at 293 K for 2j, 180 K for the others): 1m, monoclinic, P2(1)/n, a = 14.059(3), b = 12.5531(13), c = 14.8531(6) A, beta = 95.8067(12)degrees, Z = 4; 2j, triclinic, (P) over bar1, a = 10.4729(11), b = 13.5896(11), c = 9.5803(7) A, alpha = 104.764(6), beta = 103.279(7), gamma = 107.278(7)degrees, Z = 2; 2m, monoclinic, P2(1)/n, a = 14.9442(13), b = 11.990(2), c = 16.0613(4) A, beta = 114.0153(7)degrees, Z = 4; 9, monoclinic, P2(1)/n, a = 11.123(2), b = 18.433(3), c = 13.4852(4) A, beta = 108.2075(7)degrees, Z = 4. The structures were solved by direct methods and refined by full-matrix least-squares procedures to R(F, I greater than or equal to 3 sigma (I)) = 0.036, 0.052, 0.043, and 0.040, respectively, for AFC6 data for 2j and CCD data for 1m,2m, and 9. All four molecules contain six-membered OBONCC rings, with an approximately planar ON=CC segment in the educt 1m and approximately planar OBOC segments in the rearrangement products. A probable transition state geometry is derived for the isomerization process.