allyldibromoborane | 126566-51-6

• 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: allyldibromoborane
• 英文别名: dibromo(prop-2-enyl)borane
• CAS: 126566-51-6
• 化学式: C₃H₅BBr₂
• 分子量: 211.692
• InChiKey: WTZWFHJKIPMGPT-UHFFFAOYSA-N

物化性质

• 沸点：
  148.7±33.0 °C(Predicted)
• 密度：
  1.742±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.45
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  allyldibromoborane 、 甲基环己二烯 以 正己烷 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Carbometalations of Simple Alkenes with Allyldibromoborane

  摘要：

  [GRAPHICS]The allylboration of alkenes with allyldibromoborane is described. Utilizing an improved methodology for the synthesis of allyldibromoborane, 1,3-dienes, styrene, and even isolated alkenes could be carbometalated in high yield regio- and stereospecifically at 0 degrees C. This high reactivity of allyldibromoborane significantly expands the scope of carbometalations of alkenes.

  DOI：

  10.1021/ol990673q
• 作为产物：
  描述：

  四烯丙基锡 在 三溴化硼 作用下， 以 正己烷 为溶剂， 反应 1.0h， 生成 allyldibromoborane
  参考文献：
  名称：

  立体控制形式的（+/-）-platensimycin的合成。

  摘要：

  通过以下关键步骤立体选择性地合成了被称为尼古拉（Nicolaou's）的全合成关键中间体尼古拉的关键中间体的笼形结构：（i）γ-苯甲酰氧基烯酮与叔丁基二甲基甲硅烷氧基二烯之间的非对映选择性Diels-Alder反应，（ii）形成通过分子内催化的羰基缩合反应制得二氢吡喃环，以及（iii）用氢化三丁基锡和AIBN对单硫缩醛进行环戊基自由基环化。

  DOI：

  10.1021/ol801584r

文献信息

• Syntheses with organoboranes. IX. Vinyl- and 1-alkenyldichloroboranes as ethylene and 1-alkene equivalents for the Diels–Alder reaction
  作者：Marek Zaidlewicz、Jacek R Binkul、Wojciech Sokół

  DOI：10.1016/s0022-328x(98)01175-9

  日期：1999.5

  Vinyl- and 1-alkenyldichloroboranes were used as dienophiles for the Diels–Alder reaction with representative aliphatic and cyclic 1,3-dienes. The organoborane adducts were transformed into the corresponding olefins either by protonolysis or by oxidation–mesylation–reduction. Direct protonolysis of the adducts gave in most cases mixtures of olefins whereas the reduction of mesylates with lithium triethylborohydride

  乙烯基和1-烯基二氯硼烷被用作与亲脂性和环状1,3-二烯代表的狄尔斯-阿尔德反应的亲二烯体。有机硼烷加合物通过质子分解或氧化-甲磺酰化-还原转化为相应的烯烃。在大多数情况下，加合物的直接质子分解得到烯烃的混合物，而用三乙基硼氢化锂还原甲磺酸酯则可得到高纯度的纯烯烃。
• NMR study of the exchange reactions between allyltrialkyltin compounds and lewis acids part 1. Exchanges with boron tribromide and trifluoride and titanium tetrachloride
  作者：Paul Harston、James L. Wardell、Daniele Marton、Giuseppe Tagliavini、Peter J. Smith

  DOI：10.1016/s0020-1693(00)83155-2

  日期：1989.8

  Abstract Reactions between BX 3 (X = F or Br) and TiCl 4 with R 1 CHCHCH 2 SnR 3 [ I , R = Me, Bu or cyclohexyl(Cy); R 1 = H or Me] have been studied by NMR spectroscopy. Allyl group-bromine exchanges occur between I and BBr 3 at −60 °C; at higher temperatures ( c . −10 °C) I (R = Me or Bu but not Cy) reacts further to give R 2 SnBr 2 . No allyl group-fluorine exchange products were detected from

  摘要BX 3（X = F或Br）与TiCl 4与R 1 CH = CHCH 2 SnR 3 [I，R = Me，Bu或环己基（Cy）; R 1 ＝ H或Me]已经通过NMR光谱研究。烯丙基溴交换在I和BBr 3之间于-60°C进行；在较高温度（约-10°C）下，I（R = Me或Bu而不是Cy）进一步反应生成R 2 SnBr 2。在低于-20℃的条件下，I与BF 3·Et 2 O之间的反应未检测到烯丙基-氟交换产物。但是，在25°C时（R = Me，R 1 = H）容易与BF 3·Et 2 O反应，主要的可溶性锡产物为Me 4 Sn。化合物I和TiCl 4在30°C时快速生成R 3 SnCl和[RCHCHCH 2] TiCl 3。
• A Convenient Method for the Generation of Allylic Dihaloboranes and Diallyl(chloro)borane and Their Application in the Allylboration of Alkenes and Acetylenes
  作者：Yuri N. Bubnov、Nikolai Y. Kuznetsov、Fedor V. Pastukhov、Vadim V. Kublitsky

  DOI：10.1002/ejoc.200500391

  日期：2005.11

  products were isolated by standard techniques and transformed into boronates (boron amides). Deboronation of these products led to 1,4-pentadiene derivatives or unsaturated alcohols. 2-Substituted 1,4-pentadienyl(dichloro)boranes obtained from acetylenes underwent intramolecular chloroboration at a moderate temperature to form 5-chloro-2-borinene derivatives. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451

  基于 BHal3（Hal = Cl，Br）和烯丙基三有机硼烷（烯丙基、肉桂基和 2-亚甲基环丁烷衍生物）之间的交换反应，开发了一种用于高反应性烯丙基二卤代硼烷和二烯丙基（氯）硼烷的便捷方法。由此产生的化合物容易与末端烯烃和乙炔反应形成相应的顺式-1,2-烯丙基硼化产物。这些产品通过标准技术分离并转化为硼酸盐（硼酰胺）。这些产品的脱硼产生 1,4-戊二烯衍生物或不饱和醇。从乙炔获得的 2-取代的 1,4-戊二烯基（二氯）硼烷在中等温度下进行分子内氯硼化反应，形成 5-氯-2-硼烯衍生物。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• Synthesis and Characterization of Allylic Dihaloboranes
  作者：Stéphanie Le Serre、Jean-Claude Guillemin

  DOI：10.1021/om9706471

  日期：1997.12.1

  Volatile allylic dihaloboranes have been prepared and characterized by H-1, B-11, C-13, and F-19 NMR spectroscopy and mass spectrometry. The stability (tau(1/2)) of such compounds in dilute CDCl3 solutions depends on the substituents and the halides and ranges from a few minutes (allylic dibromoboranes) to several days (allylic difluoroboranes). Allyldihaloborane etherates were obtained by addition of diethyl ether to the corresponding free allyldihaloborane.
• Stereocontrolled Formal Synthesis of (±)-Platensimycin
  作者：Jun-ichi Matsuo、Kosuke Takeuchi、Hiroyuki Ishibashi

  DOI：10.1021/ol801584r

  日期：2008.9.18

  The caged structure of platensimycin, known as Nicolaou's key intermediate for total synthesis of platensimycin, was synthesized stereoselectively by using the following key steps: (i) diastereoselective Diels-Alder reaction between gamma-benzoyloxy enone and tert-butyldimethylsiloxydiene, (ii) formation of a dihydropyran ring by intramolecular catalytic oxypalladation, and (iii) transannular radical

  通过以下关键步骤立体选择性地合成了被称为尼古拉（Nicolaou's）的全合成关键中间体尼古拉的关键中间体的笼形结构：（i）γ-苯甲酰氧基烯酮与叔丁基二甲基甲硅烷氧基二烯之间的非对映选择性Diels-Alder反应，（ii）形成通过分子内催化的羰基缩合反应制得二氢吡喃环，以及（iii）用氢化三丁基锡和AIBN对单硫缩醛进行环戊基自由基环化。