trans-Hex-2-enyl phenyl selenide | 90036-65-0

• 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: trans-Hex-2-enyl phenyl selenide
• 英文别名: trans-1-phenylseleno-2-hexene；(E)-hex-2-enyl(phenyl)selane；1-phenylseleno-2-hexene；[(E)-hex-2-enyl]selanylbenzene
• CAS: 90036-65-0
• 化学式: C₁₂H₁₆Se
• 分子量: 239.219
• InChiKey: FSWQSCFPCGIJED-XBXARRHUSA-N

物化性质

• 沸点：
  286.3±23.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.79
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• 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：

  trans-Hex-2-enyl phenyl selenide 生成 [(E)-hex-2-enyl]seleninylbenzene
  参考文献：
  名称：

  LATHAM, J. A. ,, JR.;BRANCHAUD, B. P.;CHEN, Y. -C. J.;WALSH, CH., J. CHEM. SOC. CHEM. COMMUN., 1986, N 7, 528-530

  摘要：

  DOI：
• 作为产物：
  描述：

  1-甲基硒代-2-己烯 在 甲基磺酰胺 、 AD-mix-β 、 zinc(II) chloride 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 27.0h， 生成 trans-Hex-2-enyl phenyl selenide
  参考文献：
  名称：

  Oxidation of allylselenides with the Sharpless AD-reagents

  摘要：

  Allylselenides are efficiently oxidized by AD-mix reagents. Oxidation takes chemoselectively place on the selenium atom of allylselenides bearing a methylseleno or a phenylseleno moiety, but chemoselectively occurs on the C,C double bond of the corresponding omicron-nitropbenyl derivatives. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00596-0

文献信息

• Samarium(II) Di-iodide Induced Synthesis of Allylic Phenyl Selenides from Allylic Acetates and Diphenyl Diselenide in the Presence of Palladium Catalyst
  作者：Shin-ichi Fukuzawa、Tatsuo Fujinami、Shizuyoshi Sakai

  DOI：10.1246/cl.1990.927

  日期：1990.6

  Allylic phenyl selenides are prepared efficiently from the reaction of allylic acetates and diphenyl diselenide induced by samarium(II) diiodide in the presence of a palladium catalyst under mild conditions.

  在钯催化剂存在下，在温和条件下，由二碘化钐（II）诱导的烯丙基乙酸酯和二苯基二硒化物反应有效地制备烯丙基苯基硒化物。
• Iridium-Catalyzed Allylic Alkylations of Sodium Phenyl Selenide
  作者：Ruimin Cui、Xinwen Guo、Shengcai Zheng、Xiaoming Zhao

  DOI：10.1002/cjoc.201200836

  日期：2012.10.30

  An iridium‐catalyzed allylic substitution of sodium phenyl selenide with unsymmetrical allyl carbonates was accomplished, which produced the linear allyl phenyl selenides in 38%–74% yields. An asymmetric iridium‐catalyzed allylation of sodium phenyl selenide was presented as well.

  用不对称的碳酸烯丙酯进行了铱催化的苯基硒化钠的烯丙基取代，从而以38％至74％的产率生产了线性烯丙基苯基硒化物。还提出了不对称的铱催化的硒化苯硒酸钠的烯丙基化。
• Synthesis of protected allylic amines from allylic phenyl selenides: Improved conditions for the chloramine T oxidation of allylic phenyl selenides
  作者：John E. Fankhauser、Richard M. Peevey、Paul B. Hopkins

  DOI：10.1016/s0040-4039(01)91136-0

  日期：1984.1

  Anhydrous chloramine T in methanol is a highly effective reagent for the conversion of allylic phenyl selenides to the corresponding rearranged N-allylic-p-toluenesulfonamides. The reaction presumably proceeds via an allylic selenimide intermediate which undergoes [2,3]-sigmatropic rearrangement.

  甲醇中的无水氯胺T是将烯丙基苯基硒化物转化为相应的重排N-烯丙基-对甲苯磺酰胺的高效试剂。该反应大概是通过烯丙基硒酰亚胺中间体进行的，该中间体经历了[2,3]-σ重排。
• A new synthesis of secondary allylic aliphatic and aromatic amines
  作者：Andreas Spaltenstein、Philip A. Carpino、Paul B. Hopkins

  DOI：10.1016/s0040-4039(00)83963-5

  日期：1986.1

  Treatment of a variety of aliphatic or aromatic primary amines with an N-chlorosuccinimideactivated allylic setenide affords in modest to good yield the corresponding allylically rearranged secondary amines. Examples are reported which define the scope and limitations of this process.

  用N-氯代琥珀酰亚胺活化的烯丙基烯化烯处理各种脂族或芳族伯胺可适度地以良好的产率获得相应的烯丙基重排的仲胺。报告了一些示例，这些示例定义了此过程的范围和局限性。
• Allylic and propargylic phenyl selenide oxygenation by cyclohexanone oxygenase: [2,3]-sigmatraopic rearrangement of the enzyme-generated selenoxide
  作者：John A. Latham、Bruce P. Branchaud、Y.-C. Jack Chen、Christopher Walsh

  DOI：10.1039/c39860000528

  日期：——

  Enzymic oxidation of propargyloic and allylic selenides has been carried out and the resulting selenoxides found to readily undergo 2,3-sigmatropic rearrangement; the propargylic product undergoes fragmentation while the allylic product yields racemic alcohols.

  已进行炔丙基和烯丙基硒化物的酶氧化，发现所得硒氧化物易于发生2,3-σ重排；炔丙基产物发生裂解，而烯丙基产物产生外消旋醇。