tris(2,6-dimethoxyphenyl)borane | 142453-07-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: tris(2,6-dimethoxyphenyl)borane
• CAS: 142453-07-4
• 化学式: C₂₄H₂₇BO₆
• 分子量: 422.286
• InChiKey: LCYPBCGOGMBOLO-UHFFFAOYSA-N

物化性质

• 沸点：
  552.8±50.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.25
• 重原子数：
  31.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  55.38
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  tris(2,6-dimethoxyphenyl)borane 在 正丁基锂 、 Pd(ϖ-allyl)Cl(xantphos) 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 1.75h， 生成 (E)-1-(2,6-dimethoxyphenyl)-1-bis(2,6-dimethoxyphenyl)boryl-2-phenylpenta-1,4-diene
  参考文献：
  名称：

  Palladium-Catalyzed Allylation Reaction of Alkynylborates

  摘要：

  阴离子四面体硼化合物炔基（芳基）（二甘氨酰）硼酸盐在钯（0）催化剂存在下与烯丙基溴化物发生反应，生成（二甘氨酰）（三取代烯基）硼烷。烯丙基化作用发生在炔基碳 β 与硼之间，诱导阴离子硼中心上的芳基向 α 碳发生 1,2 迁移。

  DOI：

  10.1246/bcsj.20100189
• 作为产物：
  描述：

  trifluoroborane diethyl ether 、 (2,6-二甲氧基苯基)锂 以 二氯甲烷 为溶剂， 生成 tris(2,6-dimethoxyphenyl)borane
  参考文献：
  名称：

  Comparison of twists in isosteric propellers: X-ray structures of tris(2,6-dimethoxyphenyl)borane, tris(2,6-dimethoxyphenyl)methyl cation and tris(2,6-dimethoxyphenyl)methyl radical

  摘要：

  The X-ray structures of three per-o-methoxytriphenyl-X molecules were determined by direct methods. Tris(2,6-dimethoxyphenyl)borane (1), C24H27BO6, M(r) = 422.3, monoclinic, C2/c, a = 11.076 (5), b = 20.839 (8), c = 9.944 (4) angstrom, beta = 98.40 (3)-degrees, V = 2271 (1) angstrom3, Z = 4, D(x) = 1.24 g cm-3 lambda(Mo K-alpha) = 0.71073 angstrom, mu = 0.8 cm-1, F(000) = 896, T = 295 K. Refinement based on 926 unique observed reflections and 170 parameters gave a final R(F(o)) = 0.045. The tetrafluoroborate salt of the isoelectronic tris(2,6-dimethoxyphenyl)methyl cation (2), C25H27O6+.BF4-, M(r) = 510.3, triclinic, P1BAR, a = 7.214 (5), b = 12.931 (4), c = 13.633 (3) angstrom, alpha = 83.13 (2), beta = 77.70 (3), gamma = 80.56 (4)-degrees, V = 1221 (1) angstrom3, Z = 2, D(x) = 1.39 g cm-3, lambda(Cu K-alpha) = 1.5418 angstrom, mu = 9.7 cm-1, F(000) = 532, T = 110 K. Refinement based on 2393 unique observed reflections and 325 parameters gave a final R(F(o)) = 0.056. Tris(2,6-dimethoxyphenyl)methyl radical (3), C25H27O6, M(r) = 423.5, monoclinic, P2/n, a = 10.405 (1), b = 9.429 (2), c = 11.767 (2) angstrom, beta = 102.120 (9)-degrees, V = 1128.7 (6) angstrom3, Z = 2, D(x) = 1.25 g cm-3, lambda(Mo K-alpha) = 0.71073 angstrom, mu = 0.8 cm-1, F(000) = 450, T = 295 K. Refinement based on 1189 unique observed reflections and 142 parameters gave a final R(F(o)) = 0.059. The borane (1) adopts an approximate D3 conformation in the lattice at a site with crystallographic C2 symmetry and aryl twist angles of 62.8 (2) and 64.18 (2)-degrees for the special and general rings. The cation (2) adopts a general position in the lattice with approximate C2 symmetry. The aryl twist angles are 32.6 (2), 46.1 (2) and 48.9 (2)-degrees. The free radical (3) adopts a conformation that deviates markedly from the expected ground-state structure; the special ring on a crystallographic C2 axis is twisted out of the plane of coordination by only 12.3 (5)-degrees while the general rings are twisted by 61.0 (1)-degrees.

  DOI：

  10.1107/s0108768191014982

文献信息

• Tris(2-6-dimethoxephenyl) borane and its adducts
  作者：Masanori Wada、Mitsuyuki Kanzaki、Hideo Ogura、Shuichi Hayase、Tatsuo Erabi

  DOI：10.1016/0022-328x(94)24763-9

  日期：1995.1

  Tris(2,6-dimethoxyphenyl)borane, Phi(3)B (Phi = 2,6-(MeO)(2)C6H3), an air-stable crystalline compound, formed isolable 1:1 adducts with ammonia and some primary amines but not with tertiary amines, secondary amines, or sec-alkylamines. Some tetraalkylammonium tris(2,6-dimethoxyphenyl)cyanoborates [R,N][Phi(3)B-CN] are soluble both in water and in benzene, and the stearyltrimethylammonium salt is soluble even in n-hexane. The freezing point depression measurements for some tetraalkylammonium salts suggested that they are associated in benzene by several molecules.