(3-bromopropyl)dichloroborane | 118508-72-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 英文名称: (3-bromopropyl)dichloroborane
• 英文别名: (3-Bromopropyl)(dichloro)borane；3-bromopropyl(dichloro)borane
• CAS: 118508-72-8
• 化学式: C₃H₆BBrCl₂
• 分子量: 203.702
• InChiKey: MYUDSKRUAWPJQR-UHFFFAOYSA-N

物化性质

• 沸点：
  35-40 °C(Press: 15 Torr)
• 密度：
  1.498±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.74
• 重原子数：
  7
• 可旋转键数：
  2
• 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：

  (3-bromopropyl)dichloroborane 、 1-azido-4-(N-methylamino)pentane 在 盐酸 、 甲醇 作用下， 生成 N¹-methyl-N⁴-(3-bromopropyl)-1-methyl-1,4-diaminobutane dihydrochloride
  参考文献：
  名称：

  Aliphatic amino azides as key building blocks for efficient polyamine syntheses

  摘要：

  New routes to open-chain polyamines have been developed using aliphatic amino azides as common precursors for the construction of the carbon-nitrogen framework. These alpha,omega-diaminoalkane synthetic equivalents were combined with (omega-halogenoalkyl)dichloroboranes to extend the polyamine chain from the azido moiety. An extension from the free amino group can also be achieved via a Michael type addition with acrylonitrile or a reductive amination with a gamma-azido ketone. Further transformations led to a large variety of regioselectively C- or (and) N-substituted polyamines.

  DOI：

  10.1021/jo00066a028
• 作为产物：
  描述：

  3-溴丙烯 在 三乙基硅烷 、 三氯化硼 作用下， 生成 (3-bromopropyl)dichloroborane
  参考文献：
  名称：

  通过硼酸酯对环丁烷的高度对映选择性和非对映选择性合成。

  摘要：

  [分子式：见正文]用LDA对映纯（R，R）-1,2-二环己基-1,2-乙二醇1-氯-4-氰基丁基硼酸酯5进行质子化，然后用无水溴化镁处理（R）-（反式高非对映异构和对映异构纯度的-2-氰基环丁基）硼酸酯7。在至少催化量的卤化镁不存在下未观察到环丁烷形成。

  DOI：

  10.1021/ol990579+

文献信息

• An Efficient Synthesis of N,N'-Substituted Symmetrical Diamines
  作者：Michel Vaultier、Bertrand Carboni、Pilar Martinez-Fresneda

  DOI：10.1080/00397919208019266

  日期：1992.3

  Abstract N,N'-substituted symmetrical diamines are readily prepared in high yields in a one-pot procedure from diazidoalcanes and dichloroboranes. This approach has been extended to the synthesis of thermine, a tetramine isolated from Thermus Thermophilus.

  摘要 N,N'-取代的对称二胺可以通过一锅法从二叠氮烷和二氯硼烷中以高收率轻松制备。这种方法已扩展到thermine的合成，一种从嗜热栖热菌中分离的四胺。
• Synthesis and characterization of ortho-3- and meta-2-substituted carboranes through a boron-insertion reaction, including the structure of the product of a double-insertion reaction
  作者：Weilin Chen、Juston J Rockwell、Carolyn B Knobler、David E Harwell、M.Frederick Hawthorne

  DOI：10.1016/s0277-5387(99)00038-8

  日期：1999.4

  synthesized directly using this method, they can be prepared first by functionalization of the brominated products, 6a and 6b, to their respective acetate derivatives, 7a and 7b. Then, these acetate derivatives can be reduced to the alcohols, 8a and 8b, respectively. Symmetric or asymmetric double boron-insertion reactions were employed for synthesis of 1,6-bis(closo-1,2-dicarba-3-dodecaboranyl) hexane, 9

  提出了硼插入反应的例子，其中将官能化的烯烃或醇插入双糖脂离子的开放面中。两者的硼插入产品邻-和间位-carborane被合成，如闭合碳-3-（3-溴丙基）-1,2-二碳-十二硼烷，6A，和闭合碳-2-（3-溴丙基）-1， 7-二卡巴多癸硼烷，6b。尽管不能直接使用此方法直接合成邻-3-烷基和间-2-烷基羟基-碳硼烷衍生物8a或8b，但可以先通过将溴化产物6a官能化来制备它们和6b分别为它们的乙酸酯衍生物7a和7b。然后，可以将这些乙酸酯衍生物分别还原为醇8a和8b。对称或不对称的双硼插入反应采用1,6-双合成（闭合碳-1,2-二碳-3- dodecaboranyl）己烷，9，和1,4-双（闭合碳-1,2- dicarba- 3-十二硼烷基）-1-氧杂丁烷，11。这两种类型的硼插入产品，4-（闭合碳-1,2-二碳-3- dodecaboranyl）-4- oxabut -1-烯，10，和图8
• Hydroboration with Haloborane/Trialkylsilane Mixtures
  作者：Raman Soundararajan、Donald S. Matteson

  DOI：10.1021/om00009a018

  日期：1995.9

  Trialkylsilanes or dialkylsilanes react rapidly with boron trichloride in the absence of ethereal solvents or other nucleophiles to form unsolvated dichloroborane. If no substrate is present, dichloroborane disproportionates to trichloroborane and two geometric isomers of chloroborane dimer, which in turn yield monochlorodiborane and, slowly but irreversibly, diborane. All of the B-H compounds in the mixture except diborane are highly active hydroborating agents. With alkenes in the presence of sufficient boron trichloride, the products are alkyldichloroboranes. These are free from detectable contamination by dialkylchloroboranes unless more than 1 mol of hydride is present. Similar hydroboration of terminal acetylenes can be controlled to yield either (E)-1-(dichloroboryl)alkenes or 1,1-bis(dichloroboryl)alkanes, each free from significant contamination by the other. Alkyldichloroboranes with trialkylsilanes at 25 degrees C produce alkylmonochloroboranes, detected by B-11 NMR. 1,1-Bis(dichloroboryl)alkanes similarly yield 1,1-diborylalkane dimers. An alkylmonochloroborane can hydroborate a second alkene to form a dialkylchloroborane. For this purpose, differing alkyl groups may be introduced in either order, regardless of their relative steric properties. With 2 mol of trialkylsilane, alkyldichloroboranes are converted to alkylborane dimers. Boron tribromide and its bromoborane derivatives behave similarly to the chloro compounds in the examples tested.
• A New polyamine synthesis.
  作者：B. Carboni、M. Vaultier、R. Carrié

  DOI：10.1016/s0040-4039(00)80276-2

  日期：1988.1
• CARBONI, B.;VAULTIER, M.;CARRIE, R., TETRAHEDRON LETT., 29,(1988) N 11, 1279-1282
  作者：CARBONI, B.、VAULTIER, M.、CARRIE, R.

  DOI：——

  日期：——