boraadamantane-pyridine adduct | 37863-04-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: boraadamantane-pyridine adduct
• 英文别名: 1-boraadamantane * pyridine；1-pyridine-1-boraadamantane；1-(1-Boranuidatricyclo[3.3.1.13,7]decan-1-yl)pyridin-1-ium
• CAS: 37863-04-0
• 化学式: C₁₄H₂₀BN
• 分子量: 213.13
• InChiKey: IERMXJWLPVXHIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.83
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  3.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-bromo-7-bromomethyl-3-borabicyclo{3.3.1}nonane 在 吡啶 、 magnesium 作用下， 以 乙醚 为溶剂， 以67%的产率得到boraadamantane-pyridine adduct
  参考文献：
  名称：

  Organoboron化合物：CCCXCIX。3-borabicyclo [3.3.1]壬烷系列化合物的Matteson-Pasto重排

  摘要：

  3-异丙基-7-甲基-和3-异丙基-7-溴甲基-3-borabicyclo [3.3.1]壬烷的溴化反应生成相应的3-（2-溴-2-丙基）衍生物，将其用醇处理吡啶或吡啶以及加热后，进行Matteson-Pasto重排，转化为3-X-4,4,8-三甲基-和3-X-4,4-二甲基-8-溴甲基-3-borabicyclo [4.3。 1]癸烷（X = Br，OR）。三乙胺和3-（2-溴-2-丙基）-7-甲基-3-硼环[3.3.1]壬烷之间的相互作用伴随有脱氢溴化作用，导致3-异丙烯基-7-甲基-3-硼环[3.3.1] ]壬烷。3,4,4,8-四甲基-3-borabicyclo [4.3.1]癸烷在140°C的羰基化反应伴随着两个烷基从硼迁移到碳原子，随后被H 2 O 2氧化生产1-（2-羟基-2-甲基-1-丙基）-3-丙酮基-5-甲基-环己烷。在更强的条件下（180-195°C），第三烷基也迁移，在氧化后得到异构体3

  DOI：

  10.1016/s0022-328x(00)87427-6

文献信息

• 1-Pyridine- and 1-Quinuclidine-1-boraadamantane as Models for Derivatives of 1-Borabicyclo[2.2.2]octane. Experimental and Theoretical Evaluation of the B−N Fragment as a Polar Isosteric Substitution for the C−C Group in Liquid Crystal Compounds
  作者：Piotr Kaszynski、Serhii Pakhomov、Mikhail E. Gurskii、Sergey Yu. Erdyakov、Zoya A. Starikova、Konstantin A. Lyssenko、Mikhail Yu. Antipin、Victor G. Young、Yurii N. Bubnov

  DOI：10.1021/jo802504c

  日期：2009.2.20

  1-boraadamantane (2, SE = 16.5 kcal/mol). The chemical stability of 2-P and 2-Q, with respect to hydrolytic and oxidative reagents, is high for the pyridine derivative and satisfactory for the quinuclidine complex at ambient temperature, which implies sufficiently high stability of 1-borabicyclo[2.2.2]octane complexes for materials applications. Molecular dipole moments of 6.2 ± 0.1 and 6.0 ± 0.15 D were measured

  使用计算方法和对其紧密类似物1-硼烷金刚烷（2）的两种配合物进行的实验研究，评估了1-borabicyclo [2.2.2]辛烷（1）作为液晶结构元素的适用性。1-吡啶-1-硼烷金刚烷[ 2-P，C 14 H 20 BN，P 2 1 / m，a = 8.4404（13）Å，b = 6.8469（10）Å，c = 10.5269（ 16）Å，β= 104.712（3）°，Z = 2]，1-奎宁环-1-硼酸金刚烷[ 2-Q，C 16 H 28 BN，P2 1 / n，a = 6.6529（3）Å，b = 10.6665（6）Å，c = 19.3817（10）Å，β= 94.689（3）°，Z = 4]和1-吡啶-三甲基硼烷[ 3 -P，C 8 H 14 BN，C cma，a = 6.9875（10）Å，b = 15.011（2）Å，c = 16.556（2）Å，Z = 8]由X射线晶体学测定并
• 1-Boraadamantane: reactivity towards mono-1-alkynyltin, -germanium and -silicon compounds—synthesis of 4-methylene-3-borahomoadamantanes
  作者：B Wrackmeyer

  DOI：10.1016/s0022-328x(00)00746-4

  日期：2001.2.15

  The reaction of 1-boraadamantane 1 with 1-alkynyltin (3), -germanium (4), and -silicon compounds (5) leads to enlargement of the tricyclic system by formation of 4-methylene-3-borahomoadamantanes (6-9). These are 1,1-organoboration reactions which proceed by cleavage of the M-C equivalent to bond (M = Sn, Ge, Si). There is evidence for 1,1-deorganoboration which apparently take place much more readily than for non-cyclic analogues, most likely as the result of the strained tricyclic system. When 2-ethyl-1-boraadamantane (2) is used, again 3-borahomoadamantanes are formed, the isomers 15-18. The product distribution is sensitive to steric effects. However, it appears that the B-C(H)Et bond in 2 is slightly more reactive than the B-CH2 bonds. All products were characterised by H-1-, B-11-,C-13-, Si-29- and Sn-119-NMR. (C) 2001 Elsevier Science B.V. All rights reserved.
• Organoboron compounds
  作者：B.M. Mikhailov、K.L. Cherkasova

  DOI：10.1016/s0022-328x(00)98646-7

  日期：1983.4