(butyselanyl)acetylene | 136639-48-0

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (butyselanyl)acetylene
• 英文别名: 1-Ethynylselanylbutane
• CAS: 136639-48-0
• 化学式: C₆H₁₀Se
• 分子量: 161.105
• InChiKey: HCUQOAKEGXHMDR-UHFFFAOYSA-N

物化性质

• 沸点：
  168.5±23.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  7
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  (butyselanyl)acetylene 在 Schwartz's reagent 、 水 作用下， 生成 butylselanyl-ethene
  参考文献：
  名称：

  Hydrozirconation of acetylenic chalcogenides. Synthesis and reactions of zirconated vinyl chalcogenide intermediates

  摘要：

  Acetylenic tellurides react with Cp2Zr(H)Cl in THF at room temperature to give the alpha-zirconated vinyl telluride intermediates 39, which react with a wide range of electrophiles to give several types of trisubstituted olefins, such as alpha-halo vinyl tellurides, ketene telluro(seleno) acetals, ketene telluro acetals, and vinylic tellurides of Z configuration. Acetylenic selenides undergo similar reactions, but a lack of regioselectivity results in the formation of a mixture of alpha-zirconated 19 and beta- zirconated 20 vinylic selenide intermediates. After a derailed study was established that the use of 2.0 equivalents of Cp2Zr(H)Cl is crucial to perform the total hydrozirconation of acetylenic selenides or tellurides. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00014-3
• 作为产物：
  描述：

  4-(butylselanyl)-2-methylbut-3-yn-2-ol 在 potassium hydroxide 作用下， 以 正己烷 为溶剂， 反应 3.0h， 以53%的产率得到(butyselanyl)acetylene
  参考文献：
  名称：

  基于羟基炔丙基前体的逆向-Favorskii反应合成末端乙炔基芳基硒化物和硫化物

  摘要：

  Favorskii逆反应是获得末端炔烃的绝佳方法。连接末端炔烃和有机硫属元素基团的合成的方法对于构建新型化合物很重要。通过逆向Favorskii反应从相应的甲醇前体中选择性地制备了十四个含有C sp -S或C sp -Se键的新末端炔烃。已经发现，如果以溶液形式储存在末端硫属元素炔烃可以稳定数周。

  DOI：

  10.1002/chem.201702493

文献信息

• Regio-and Stereoselective Synthesis of (E)-1-Alkylseleno-1, 4-Pentadienes by Cross-Coupling of Allyl Bromide with Alkyl-selenovinylcoppers from Alkylselenovinyldialkylboranes
  作者：De-Yu Yang、Xian Huang

  DOI：10.1080/00397919608003839

  日期：1996.12

  cuprous bromide-methyl sulfide to generate alkylselenovinylcopper intermediates which underwent stereospecific cross-coupling with allyl bromide to yield (E)-1-alkylseleno-1, 4-pentadienes 3. The compounds 3 were formed with retention of configuration predetermined from the stereochemistry of the initial alkylselenovinylboranes.

  摘要 烷基硒乙烯基二烷基硼烷衍生物是通过末端烷基硒炔乙炔 1 与二烷基硼烷 2 的硼氢化反应获得的，在 -15°C 下用甲醇钠和溴化亚铜 - 甲基硫化物处理生成烷基硒乙烯基铜中间体，该中间体与烯丙基溴进行立体有择交叉偶联得到 (E)- 1-烷基硒基-1, 4-戊二烯3。化合物3形成时保留了由初始烷基硒乙烯基硼烷的立体化学预先确定的构型。
• A Stereoselective Route to (E)-Vinylic Selenides through the Palladium-Catalyzed Cross-Coupling Reaction of Selenovinylicdialkylboranes with Alkyl Halides
  作者：Yu Yang、Xian Huang

  DOI：10.1080/00397919708005038

  日期：1997.1

  Abstract The reaction of selenoviylicdialkyboranes with alkyl halides takes place readily in the presence of Pd(PPh3)4 and sodium methoxide to afford (E)-vinylic selenides in excellent yields

  摘要 在 Pd(PPh3)4 和甲醇钠的存在下，硒乙烯基二烷基硼烷与卤代烷的反应很容易发生，以优异的产率得到 (E)-乙烯基硒化物。
• Regio- and Stereoselective Conversion of Terminal Alkylselenoacetylenes into (E)-2-Alkylseleno-1-Vinylic Iodides via Hydroboration-Iodination
  作者：De-Yu Yang、Xian Huang

  DOI：10.1080/00397919608004786

  日期：1996.12

  The hydroboration of terminal alkylselenoacetylenes 1 in the presence of 3 mol% of Pd (PPh(3))(4) with catecholborane 2 followed by hydrolysis, undergo a rapid reaction with iodine under the influence of sodium hydroxide at-10 degrees C in THF to afford a novel method for the regio-and stereospecific synthesis of (E)-2-alkylseleno-1-vinyl iodides 4.
• AMOSOVA, S. V.;POTAPOV, V. A.;KEJKO, V. V.;ROMANENKO, L. S.;VITKOVSKIJ, V+, METALLOORGAN. XIMIYA, 4,(1991) N, S. 950-951
  作者：AMOSOVA, S. V.、POTAPOV, V. A.、KEJKO, V. V.、ROMANENKO, L. S.、VITKOVSKIJ, V+

  DOI：——

  日期：——
• Hydrozirconation of acetylenic chalcogenides. Synthesis and reactions of zirconated vinyl chalcogenide intermediates
  作者：Miguel J. Dabdoub、Mauro L. Begnini、Palimécio G. Guerrero

  DOI：10.1016/s0040-4020(98)00014-3

  日期：1998.3

  Acetylenic tellurides react with Cp2Zr(H)Cl in THF at room temperature to give the alpha-zirconated vinyl telluride intermediates 39, which react with a wide range of electrophiles to give several types of trisubstituted olefins, such as alpha-halo vinyl tellurides, ketene telluro(seleno) acetals, ketene telluro acetals, and vinylic tellurides of Z configuration. Acetylenic selenides undergo similar reactions, but a lack of regioselectivity results in the formation of a mixture of alpha-zirconated 19 and beta- zirconated 20 vinylic selenide intermediates. After a derailed study was established that the use of 2.0 equivalents of Cp2Zr(H)Cl is crucial to perform the total hydrozirconation of acetylenic selenides or tellurides. (C) 1998 Elsevier Science Ltd. All rights reserved.