1-iodo-1-dodecene | 197390-82-2

• 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: 1-iodo-1-dodecene
• 英文别名: 1-iodododecene；Iodododecene；1-iodododec-1-ene
• CAS: 197390-82-2
• 化学式: C₁₂H₂₃I
• 分子量: 294.219
• InChiKey: CLEAYYZTUNNTKM-UHFFFAOYSA-N

物化性质

• 沸点：
  285.6±9.0 °C(Predicted)
• 密度：
  1.230±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  13
• 可旋转键数：
  9
• 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：

  1-iodo-1-dodecene 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 15.0h， 以96%的产率得到1-十二烯十二碳烯α-十二碳烯α-十二碳烯
  参考文献：
  名称：

  电子转移诱导的胺类还原有机卤化物†

  摘要：

  通过使用胺作为牺牲氢源，研究了各种有机卤化物的还原。UV光诱导的三乙胺对乙烯基卤化物和芳基卤化物的还原反应顺利进行，得到了相应的还原产物。高温加热也引起了还原，DABCO（1,4-二氮杂双环[2.2.2]辛烷）也用作良好的还原剂。

  DOI：

  10.1039/c8cc02445f
• 作为产物：
  描述：

  1-十二炔 在 三乙基硼 、 dichlorogallane 、 碘 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 4.0h， 生成 1-iodo-1-dodecene
  参考文献：
  名称：

  Triethylborane-Mediated Hydrogallation and Hydroindation:  Novel Access to Organogalliums and Organoindiums

  摘要：

  Hydrogallation of carbon-carbon multiple bonds proceeds in the presence of triethylborane as a radical initiator. Several functionalities do not interfere with this reaction. Resulting alkenyl- and alkylgallium species can be trapped by several electrophiles. Highly regioselective radical addition of an indium hydride reagent to alkynes is also achieved. Various functionalities are tolerant under the reaction conditions. The reaction proceeds with complete anti stereoselectivity. Alkenylindiums obtained via hydroindation can be employed for the following cross-coupling reaction with aryl halides in one pot.

  DOI：

  10.1021/jo0344790

文献信息

• Radical Allylation, Vinylation, Alkynylation, and Phenylation Reactions of α-Halo Carbonyl Compounds with Organoboron, Organogallium, and Organoindium Reagents
  作者：Koichiro Oshima、Kazuaki Takami、Shin-ichi Usugi、Hideki Yorimitsu

  DOI：10.1055/s-2005-861846

  日期：——

  reactions of α-halo carbonyl compounds with alkenylindium proceeded via a radical process in the presence of triethylborane. Unactivated alkene moieties and styryl groups were introduced by this method. The carbon-carbon double bond geometry of the alkenylindiums was retained during the alkenylation. Preparation of an alkenylindium via a hydroindation of 1-alkyne and subsequent radical alkenylation established

  发现烯丙基镓和铟试剂可介导 α-碘或 α-溴羰基化合物的自由基烯丙基化反应。在三乙基硼烷的存在下，用由烯丙基氯化镁和三氯化镓制备的烯丙基镓处理溴乙酸苄酯，以极好的收率提供了4-戊烯酸苄酯。添加水作为助溶剂提高了烯丙基化产物的产率。烯丙基铟试剂也是有用的并且可以代替镓试剂。二烯丙基硼烷试剂可以以良好的产率烯丙基化 α-碘酯。在三乙基硼烷存在下，α-卤代羰基化合物与烯基铟的烯基化反应通过自由基过程进行。通过该方法引入了未活化的烯烃部分和苯乙烯基。烯基化过程中保留了烯基铟的碳-碳双键几何结构。通过 1-炔烃的氢化和随后的自由基烯基化制备烯基铟建立了一种有效的一锅法。本文公开了用有机铟试剂进行的自由基炔基化和苯基化。
• Synchronous bond molecular dynamics of conjugated chlorocyclopropyl alk‐yn‐enes revealed by ECD and UV–vis
  作者：Colin K. Skepper、Tadeusz F. Molinski

  DOI：10.1002/chir.23240

  日期：2020.8

  Chlorocyclopropanes (CCPs) conjugated to alk‐yn‐enes occur in a unique family of polyketide natural products from marine sponges. Synthesis of several optically enriched analogs of CCPs and measurement of their UV–vis spectra and electronic circular dichroism (ECD) spectra reveal unusually strong hyperconjugation that constrains and aligns the cyclopropyl C‐C bond with the π‐plane of the distal ene‐bond

  与炔烃共轭的氯环丙烷（CCP）存在于海洋海绵的独特的聚酮化合物天然产物家族中。几种CCP的光学富集类似物的合成以及它们的UV-vis光谱和电子圆二色性（ECD）光谱的测量揭示了异常强的超共轭，该超共轭将环丙基C-C键约束并与远侧烯键的π平面对齐。该对准施加至少5.0kcal·mol -1的旋转障碍。手性CCP中红移棉效应的比较表明，该屏障独立于烯烃取代基，并为其他含CCP天然产物的分配建立了经验规则。
• Homogeneous catalytic aminocarbonylation of 1-iodo-1-dodecene. The facile synthesis of odd-number carboxamides via palladium-catalysed aminocarbonylation
  作者：Attila Takács、Péter Ács、Roland Farkas、George Kokotos、László Kollár

  DOI：10.1016/j.tet.2008.08.022

  日期：2008.10

  Various amine nucleophiles including glycine methyl ester were used in the palladium-catalysed aminocarbonylation of (E)- and (Z)-1-iodo-1-dodecene. The substrates were synthesised from 1-dodecanal via the corresponding hydrazone, which was treated with iodine in the presence of tetramethylguanidine. The homogeneous catalytic aminocarbonylation resulted in the corresponding odd-number carboxamides

  在（E）-和（Z）-1-碘-1-十二碳烯的钯催化的氨基羰基化反应中使用了包括甘氨酸甲酯在内的各种胺亲核试剂。底物是通过相应的从1-十二指肠合成的，,在四甲基胍的存在下用碘处理。均相催化氨基羰基化以中等至良好的产率产生了相应的奇数羧酰胺。该反应伴随有一些在2-位具有三键的羧酰胺的形成。后者的产物是用仲胺如哌啶和吗啉以相对高的收率形成的，并被分离为纯化合物。
• Radical Alkenylation of α-Halo Carbonyl Compounds with Alkenylindiums
  作者：Kazuaki Takami、Hideki Yorimitsu、Koichiro Oshima

  DOI：10.1021/ol048070o

  日期：2004.11.1

  Alkenylation reaction of alpha-halo carbonyl compounds with alkenylindiums proceeded via a radical process in the presence of triethylborane. Unactivated alkene moieties as well as a styryl group could be introduced by this method. The geometry of the carbon-carbon double bonds of the alkenylindiums was retained. Preparation of an alkenylindium via a hydroinclation of 1-alkyne followed by radical alkenylation established an efficient one-pot strategy.
• Ene-yne Tetrahydrofurans from the Sponge <i>Xestospongia muta</i>. Exploiting a Weak CD Effect for Assignment of Configuration
  作者：Brandon I. Morinaka、Colin K. Skepper、Tadeusz F. Molinski

  DOI：10.1021/ol0705696

  日期：2007.5.1

  Seven new brominated ene-yne tetrahydrofurans (THFs), mutafurans A-G, were isolated from the Bahamian sponge Xestospongia muta. The absolute configuration of the natural products was assigned as (5R, 8S) by interpretation of the Cotton effect arising from weak perturbation of an ene-yne chromophore by a propargylic THF ring.