(1E)-1-hexen-1-yldibromoborane-dimethyl sulfide | 72228-56-9

• 分子结构分类: 有机化合物 - 有机磷化合物
• 英文名称: (1E)-1-hexen-1-yldibromoborane-dimethyl sulfide
• 英文别名: 1(E)-hex-1-en-1-yldibromoborane dimethyl sulfide；dibromo-[(E)-hex-1-enyl]borane;methylsulfanylmethane
• CAS: 72228-56-9
• 化学式: C₂H₆S*C₆H₁₁BBr₂
• 分子量: 315.908
• InChiKey: ICCKWPLMAXVYSY-IPZCTEOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.53
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1E)-1-hexen-1-yldibromoborane-dimethyl sulfide 、 苯酚 以83%的产率得到
  参考文献：
  名称：

  BROWN, H. C.;BHAT, N. G.;SOMAYAJI, V., ORGANOMETALLICS, 1983, 2, N 10, 1311-1316

  摘要：

  DOI：
• 作为产物：
  描述：

  1-己炔 、 dibromoborane-methyl sulfide complex 生成 (1E)-1-hexen-1-yldibromoborane-dimethyl sulfide
  参考文献：
  名称：

  乙烯基二氯硼烷的亲烯活性及其在Diels-Alder中的伴侣的使用-一锅反应中叠氮化物的还原烷基化

  摘要：

  乙烯基二氯硼烷与1,3-二烯反应，序列Diels-Alder环加成-苄基叠氮化物的还原烷基化直接导致仲胺，因此，表明乙烯基二氯硼烷与定义立体化学的仲烯胺的合成等同物一样。

  DOI：

  10.1039/c39920001105

文献信息

• Hydroboration. 55. Hydroboration of alkynes with dibromoborane-dimethyl sulfide. Convenient preparation of alkenyldibromoboranes
  作者：Herbert C. Brown、James B. Campbell

  DOI：10.1021/jo01291a004

  日期：1980.2
• BROWN, HERBERT C.;SUBRAHMANYAM, CHITTI;HAMAOKA, TSUTOMU;RAVINDRAN, NAIR;B+, J. ORG. CHEM., 54,(1989) N6, C. 6068-6075
  作者：BROWN, HERBERT C.、SUBRAHMANYAM, CHITTI、HAMAOKA, TSUTOMU、RAVINDRAN, NAIR、B+

  DOI：——

  日期：——
• Kinetics and mechanism of hydroboration reactions of HBBr2·SMe2 and HBCl2·SMe2 – Application of 11B NMR spectroscopy
  作者：D. Jaganyi、N. Xaba、A. Mzinyati、C. Grimmer

  DOI：10.1016/j.jorganchem.2006.11.021

  日期：2007.2

  The kinetics and mechanism of the hydroboration reactions of 1-octene with HBBr2 center dot SMe2 and HBCl2 center dot SMe2, in CH2Cl2 as a solvent, were studied. Rates of hydroboration were monitored using B-11 NMR spectroscopy. The reactions exhibited simple second-order kinetics of the form k(obs) = k(2)(')[Nu]. The HBCl2 center dot SMe2 was found to be 20 times more reactive than the HBBr2 center dot SMe2). The overall activation parameters (Delta H-not equal, Delta S-not equal) for the reaction of HBBr2 center dot SMe2 with 1-octene were found to be 82 +/- 1 kJ mol(-1), -18 +/- 4 J K-1 mol(-1) and with 1-hexyne were 78 +/- 4 kJ mol(-1) -34 +/- 12 J K-1 mol(-1). For the reaction of HBCl2 center dot SMe2 with 1-octene, Delta H-not equal and Delta S-not equal were 104 +/- 5 kJ mol(-1) and 43 +/- 16 J K-1 mol(-1), respectively. The activation parameters (Delta H-not equal, Delta S-not equal) for the dissociation of Me2S from HBBr2 center dot SMe2 were found to be 104 +/- 2 kJ mol(-1), +33 +/- 8 J K-1 mol(-1), respectively. Based on the activation parameters, it was concluded that the detaching of Me,S from the boron centre follows a dissociative mechanism, while the hydroboration process follows an associative pathway. It was also concluded that the dissociation of Me2S from the boron centre is the rate determining step. (c) 2006 Elsevier B.V. All rights reserved.