(E)-6-iodo-6-dodecene | 136679-10-2

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: (E)-6-iodo-6-dodecene
• 英文别名: (E)-6-iodododec-6-ene
• CAS: 136679-10-2
• 化学式: C₁₂H₂₃I
• 分子量: 294.219
• InChiKey: YIGARCDREOEKFA-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  (E)-6-iodo-6-dodecene 在 lithium dibutyl(isopropyl)magnesate 、 重水 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 以87%的产率得到(Z)-6-deuteriododec-6-ene
  参考文献：
  名称：

  Halogen-Magnesium Exchange via Trialkylmagnesates for the Preparation of Aryl- and Alkenylmagnesium Reagents

  摘要：

  DOI：

  10.1002/1521-3773(20000717)39:14<2481::aid-anie2481>3.0.co;2-j
• 作为产物：
  描述：

  6-十二炔 在 二氯二茂钛 碘 、 lithium hydride 、 zinc(II) iodide 作用下， 生成 (E)-6-iodo-6-dodecene
  参考文献：
  名称：

  Stereo- and Regioselective Generation of Alkenylzinc Reagents via Titanium-Catalyzed Hydrozincation of Internal Acetylenes

  摘要：

  DOI：

  10.1021/jo00107a003

文献信息

• Stereoselective synthesis of di- and trisubstituted alkenes via intermolecular addition of vinyl radicals to alkenes
  作者：Katsukiyo Miura、Daisuke Itoh、Takeshi Hondo、Akira Hosomi

  DOI：10.1016/0040-4039(94)88522-2

  日期：1994.12

  Vinyl radicals, generated from the reaction of vinyl iodides with tributylstannyl radical, react with electron-deficient alkenes to give di- or trisubstituted alkenes in moderate to good yields. The stereoselectivity is largely dependent on the substituent at 1- and 2-position of vinyl iodides.

  由乙烯基碘与三丁基锡烷基反应生成的乙烯基与缺电子的烯烃反应，以中等至良好的收率得到二或三取代的烯烃。立体选择性主要取决于乙烯基碘的1-和2-位上的取代基。
• A facile preparation of alkenyl- and allenylmetallic compounds by means of iodine-metal exchange and their use in organic synthesis
  作者：Hiroshi Shinokubo、Hiroaki Miki、Toshiaki Yokoo、Koichiro Oshima、Kiitiro Utimoto

  DOI：10.1016/0040-4020(95)00700-i

  日期：1995.10

  Stereospecific lithium-halogen exchange of alkenyl iodides was performed upon treatment with butyllithium in non-polar solvents such as hexane, benzene, and toluene at 25 °C to provide alkenyllithiums quantitatively with retention of the configuration. Metal-iodine exchange of allenyl iodides with n-BuLi, i-PrMgBr or Et2Zn was also performed effectively to afford the corresponding allenylmetallic reagents

  在非极性溶剂（如己烷，苯和甲苯）中于25°C用丁基锂处理后，进行烯基碘的立体定向锂-卤素交换，以定量提供具有构型保留的烯基锂。还有效地进行了烯基碘化物与n -BuLi ，i -PrMgBr或Et 2 Zn的金属-碘交换，从而提供了相应的烯基金属试剂。在金属试剂中加入羰基化合物可得到具有高区域选择性的均丙炔醇，收率很高。
• Palladium Catalyzed Stereoselective Hydrodehalogenation of Alkenyl Halides with Tributyltin Hydride
  作者：Masahiko Taniguchi、Yoshihiro Takeyama、Keigo Fugami、Koichiro Oshima、Kiitiro Utimoto

  DOI：10.1246/bcsj.64.2593

  日期：1991.8

  The reduction of alkenyl halides with tributyltin hydride in the presence of a catalytic amount of tetrakis(triphenylphosphine)palladium has been studied. Alkenyl iodides reacted easily with tributyltin hydride at 25°C to give the corresponding hydrocarbons stereoselectively. However, the reaction of alkenyl bromides were sluggish at 25°C and needed heating at 75°C to complete.

  研究了在催化量的四（三苯基膦）钯存在下用氢化三丁基锡还原烯基卤化物。烯基碘化物在 25°C 下很容易与三丁基氢化锡反应，立体选择性地得到相应的烃。然而，烯基溴化物的反应在 25°C 时反应缓慢，需要在 75°C 下加热才能完成。
• Isomerization of Olefins by Means of R₃SnH–Et₃B and Stereochemical Study on Reduction of Alkenyl Iodides
  作者：Masahiko Taniguchi、Kyoko Nozaki、Katsukiyo Miura、Koichiro Oshima、Kiitiro Utimoto

  DOI：10.1246/bcsj.65.349

  日期：1992.2

  Isomerization of olefins with R3SnH–Et3B (R = Ph or n-Bu) system has been studied. Treatment of (Z)-1-triphenylstannyl-1-octene (1) or (E)-1-triphenylstannyl-1-octene (2) with a catalytic amount of Ph3SnH–Et3B provided an equilibrium mixture of 1/2 = 2/8. Partial isomerization was observed in the reaction of trivial alkenes such as 6-dodecene and 2,2-dimethyl-3-dodecene with R3SnH–Et3B system. Whereas

  已经研究了用 R3SnH–Et3B（R = Ph 或 n-Bu）系统异构化烯烃。用催化量的 Ph3SnH–Et3B 处理 (Z)-1-三苯基甲锡烷基-1-辛烯 (1) 或 (E)-1-三苯基甲锡烷基-1-辛烯 (2) 提供了 1/2 = 2/ 的平衡混合物8. 在普通烯烃如 6-十二碳烯和 2,2-二甲基-3-十二碳烯与 R3SnH-Et3B 体系的反应中观察到部分异构化。而 (Z)- 或 (E)-6-十二烯在 -78 °C 下用 n-Bu3SnH–Et3B 处理 3 小时后，在搅拌 (Z)-6-十二烯、Ph3SnH 和 Et3B 的苯溶液后，未发生变化在 60 °C 下保持 5 小时，得到 (Z)-6-十二烯和 (E)-6-十二烯 (Z/E = 64/36) 的异构混合物。考虑到这些结果，研究了在-78°C 下用 R3SnH-Et3B 系统还原烯基碘的立体化学。
• Selective Halogen−Magnesium Exchange Reaction via Organomagnesium Ate Complex
  作者：Atsushi Inoue、Kazuya Kitagawa、Hiroshi Shinokubo、Koichiro Oshima

  DOI：10.1021/jo015597v

  日期：2001.6.1

  Halogen-magnesium exchange of various aryl halides is achieved with a magnesium ate complex at low temperatures; Tributylmagnesate ((Bu3MgLi)-Bu-n) induces facile iodine-magnesium exchange at -78 degreesC. Dibutylisopropylmagnesate ((PrBu2MgLi)-Pr-i-Bu-n) is more reactive than (Bu3MgLi)-Bu-n, and this reagent accomplishes selective bromine-magnesium exchange at -78 degreesC. This procedure is utilized for the preparation of various polyfunctionalized arylmagnesium species. The exchange of alkenyl halides using this method proceeds with retention of configuration of the double bond.