1-bromo-3,3-bis(2′-bromoethyl)octane | 203931-65-1

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机溴化物
• 英文名称: 1-bromo-3,3-bis(2′-bromoethyl)octane
• 英文别名: 1-bromo-3,3-bis(2-bromoethyl)octane
• CAS: 203931-65-1
• 化学式: C₁₂H₂₃Br₃
• 分子量: 407.027
• InChiKey: CGWADPPHPOEGCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  15
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  sodium 1.carba/closo-dodecaborane-1-amide 、 1-bromo-3,3-bis(2′-bromoethyl)octane 在 K₂CO₃ 、 catalyst: 18-crown-6 作用下， 以 乙腈 为溶剂， 以29%的产率得到1-(4-pentylquinuclidin-1-yl)-1-carba-closo-dodecaborane
  参考文献：
  名称：

  Synthesis and Molecular Structure of 12-Iodo-1-(4-pentylquinuclidin-1-yl)-1-carba-closo-dodecaborane

  摘要：

  Trialkylation of 1-amino-1-carba-closo-dodecabarane with 1-bromo-3,3-bis(2-bromoethyl)octane affords 1-(4-pentylquinuclidin-1-yl)-1-carba-closo-dodecaborane in 29% yield which can then be iodinated to form title compound 1 in 40% yield. The molecular and crystal structure of 1 has been determined by X-ray crystallography [C13H33B11IN, monoclinic P2(1)/c: a 10.3405(2) Angstrom, b = 16.4404(1) Angstrom, c = 12.7223(2) Angstrom, beta = 100.156(1)degrees, Z = 4]. The structural features of 1 are compared with those in analogous compounds. The B-I bond length (2.196(6) Angstrom) is an intermediate value between those found in neutral iodocarboranes and charged B12H11I(-2). NMR data is correlated with the structure of 1 and the additivity of NR3 and halogen substituent effects is tested.

  DOI：

  10.1021/ic980775x
• 作为产物：
  描述：

  methyl (4-n-pentyl-4-tetrahydro-4H-pyranyl)cyanoacetate 在 lithium aluminium tetrahydride 、 硫酸 、 氢溴酸 、 sodium carbonate 、 十六烷基三丁基溴化磷 作用下， 以 乙醚 为溶剂， 反应 117.5h， 生成 1-bromo-3,3-bis(2′-bromoethyl)octane
  参考文献：
  名称：

  1-溴-3,3-双（2-溴乙基）烷烃：4-取代奎宁环和1-磷杂双环[2.2.2]辛烷的前体

  摘要：

  摘要 1-Bromo-3,3-bis(2-bromoethyl)octane 由四氢-4H-pyran-4-one 分 6 步合成，总产率为 18%。这种方法更方便，总产率更高，并且可能比之前报道的相关三溴化物更通用。

  DOI：

  10.1080/00397919808005108

文献信息

• Synthesis and Characterization of Quinuclidinium Derivatives of the [<i>closo</i>-1-CB₁₁H₁₂]⁻ Anion as Potential Polar Components of Liquid Crystal Materials
  作者：Jacek Pecyna、Piotr Kaszyński、Bryan Ringstrand、Damian Pociecha、Serhii Pakhomov、Andrew G. Douglass、Victor G. Young

  DOI：10.1021/acs.inorgchem.6b00319

  日期：2016.4.18

  high temperature in-plane ordered smectic phases that are stabilized by dipolar interactions. The ordered phases were investigated by powder XRD methods. Thermal and dielectric parameters for two derivatives, 1[0] and 1[6], were evaluated in nematic hosts, ClEster and BPhF. The dielectric data were analyzed with the Maier-Meier formalism augmented with density functional theory methods, and the results

  的[对映的取代闭合碳-1-CB 11 ħ 12 ] -阴离子与一个4 pentylquinuclidinium片段和在位置烷基C（1）和B（12），得到极性两性离子1 [N]和2 [n]的。的分子结构1 [5]使用X射线衍射成立（XRD）方法：P 1，一个= 15.162（2）埃，b = 16.546（3）埃，c ^ = 19.794（3）; α= 84.871（2）°，β= 84.057（2）°，γ= 84.058（3）°; ž＝ 8。所有化合物均表现出高温面内有序近晶相，其通过偶极相互作用而稳定。通过粉末XRD方法研究有序相。在向列型宿主ClEster和BPhF中评估了两个导数1 [0]和1 [6]的热和介电参数。用Maier-Meier形式主义和密度泛函理论方法对电介质数据进行了分析，并将结果与​​先前报道的类似两性离子进行了比较。
• 1-Bromo-3,3-<i>bis</i>(2-bromoethyl)alkanes: Precursors to 4-Substituted Quinuclidines and 1-Phosphabicyclo[2.2.2]octanes
  作者：Kerim A. Bairamov、Andrew G. Douglass、Piotr Kaszynski

  DOI：10.1080/00397919808005108

  日期：1998.2

  Abstract 1-Bromo-3,3-bis(2-bromoethyl)octane has been synthesized from tetrahydro-4H-pyran-4-one in 6 steps and 18% overall yield. This method is more convenient, gives higher overall yields and is potentially more general than those previously reported for related tribromides.

  摘要 1-Bromo-3,3-bis(2-bromoethyl)octane 由四氢-4H-pyran-4-one 分 6 步合成，总产率为 18%。这种方法更方便，总产率更高，并且可能比之前报道的相关三溴化物更通用。
• Synthesis and Molecular Structure of 12-Iodo-1-(4-pentylquinuclidin-1-yl)-1-carba-<i>c</i><i>loso</i>-dodecaborane
  作者：Andrew G. Douglass、Zbynek Janousek、Piotr Kaszynski、Victor G. Young

  DOI：10.1021/ic980775x

  日期：1998.11.1

  Trialkylation of 1-amino-1-carba-closo-dodecabarane with 1-bromo-3,3-bis(2-bromoethyl)octane affords 1-(4-pentylquinuclidin-1-yl)-1-carba-closo-dodecaborane in 29% yield which can then be iodinated to form title compound 1 in 40% yield. The molecular and crystal structure of 1 has been determined by X-ray crystallography [C13H33B11IN, monoclinic P2(1)/c: a 10.3405(2) Angstrom, b = 16.4404(1) Angstrom, c = 12.7223(2) Angstrom, beta = 100.156(1)degrees, Z = 4]. The structural features of 1 are compared with those in analogous compounds. The B-I bond length (2.196(6) Angstrom) is an intermediate value between those found in neutral iodocarboranes and charged B12H11I(-2). NMR data is correlated with the structure of 1 and the additivity of NR3 and halogen substituent effects is tested.