2-bromohexyl phenyl selenide | 63831-75-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-bromohexyl phenyl selenide
• 英文别名: 2-bromo-1-phenylselanylhexane；2-bromohexylselanylbenzene
• CAS: 63831-75-4
• 化学式: C₁₂H₁₇BrSe
• 分子量: 320.131
• InChiKey: GDYZPAPWXRIBCF-UHFFFAOYSA-N

物化性质

• 沸点：
  332.3±34.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.39
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  苯基溴化硒 在 calcium chloride 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 26.17h， 生成 2-bromohexyl phenyl selenide
  参考文献：
  名称：

  二溴化硒和 PhSeBr 的显着的烯烃到烯烃和烯烃到炔烃的转移反应。二卤化硒与环烯烃的立体选择性加成

  摘要：

  本研究的最初目标是研究二卤化硒加成到环烯烃的立体化学和所得产物的性质。在这项研究中发现了显着的二溴化硒和 PhSeBr 的烯烃到烯烃和烯烃到炔烃的转移反应。二溴化硒与烯烃或环烯烃的加合物在室温下在乙腈中很容易与其他不饱和化合物（包括乙炔）交换 SeBr2。PhSeBr 加合物与烯烃或环烯烃发生类似的烯烃到烯烃和烯烃到炔烃的转移反应。假设的反应途径包括硒基团从硒物种转移到烯烃或炔烃。发现有效的SeBr2和PhSeBr转移试剂是Se(CH2CH2Br)2和PhSeCH2CH2Br，它们释放乙烯，导致平衡的移动。双(E-2-溴乙烯基)硒化物和不对称E-2-溴乙烯基硒化物的区域选择性和立体选择性合成是基于SeBr2和PhSeBr转移反应开发的，与SeBr2和PhSeBr与炔烃的类似加成反应相比，该反应具有更高的选择性相同的条件。

  DOI：

  10.3390/molecules25010194

文献信息

• Synthesis of Azetidine and Pyrrolidine Derivatives through Selenium-Induced Cyclization of Secondary Homoallylamines − A77Se NMR Study
  作者：Xavier Pannecoucke、Francis Outurquin、Claude Paulmier

  DOI：10.1002/1099-0690(200203)2002:6<995::aid-ejoc995>3.0.co;2-a

  日期：2002.3

  Treatment of alpha-alkyl and alpha,alpha-dialkyl homoallylic amines I with PhSeX (X = Cl, Br, 1), in CH3CN containing sodium carbonate produced mixtures of azetidines 2 and pyrrolidines 3. The cyclization also occurred in the absence of Na2CO3, and the corresponding azetidinium and pyrrolidinium salts 2(HX) and 3(HX) were formed in CDCl3 or CH3CN. The crude reaction mixtures were analysed by Se-77 NMR. Each product - 2, 3, 2(HX), and 3(HX) - was characterized by its 77 Se chemical shift, and the product ratios were determined for each reaction. The ratios of azetidine 2 to pyrrolidine 3 increased not only according to the steric hindrance around the alpha-carbon, but also with the nature of the counterion X- (PhSeCl < PhSeBr < PhSeI). Use of PhSeI and amines 1g to 1k (R-1, R-2, not equalH), produced only the azetidinium. salts 2(HI), allowing the isolation of the corresponding azetidines 2, albeit in poor yield. Some reactions were monitored by Se-77 NMR at the beginning of the addition-cyclization process. No intermediates were observed when PhSeI was used, but the thermodynamic addition products 5(Br), 5(HBr), and some dibromose-lenuranes 8 were detected. (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
• Reactions of areneselenenamides with alkenes in the presence of phosphorus(V) and sulfur(IV) oxyhalides. New synthesis of β-haloalkyl selenides
  作者：R. L. Antipin、V. N. Klak、E. K. Beloglazkina、N. V. Zyk

  DOI：10.1134/s1070428009060062

  日期：2009.6

  A new procedure was proposed for activation of areneselenenamides with phosphorus(V) and sulfur(IV) oxyhalides. According to the (1)H, (13)C, and (31)P NMR data, areneselenenamide reacts with phosphorus oxyhalide to form intermediate adduct in which the phosphorus atom is coordinated at the selenium. Areneselenenamides activated by phosphorus(V) oxyhalides react with alkenes (norbornene and norbornadiene) with high trans-stereoselectivity. Their reactions with terminal olefins are regioselective, and they lead to preferential formation of the corresponding Markovnikov adducts.