(4,4-diiodoobut-3-enyl)benzene | 218902-80-8

• 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: (4,4-diiodoobut-3-enyl)benzene
• 英文别名: 1,1-diiodo-4-phenyl-1-butene；4,4-Diiodobut-3-enylbenzene
• CAS: 218902-80-8
• 化学式: C₁₀H₁₀I₂
• 分子量: 383.998
• InChiKey: GWCFOJNNQSSVFH-UHFFFAOYSA-N

物化性质

• 沸点：
  338.9±42.0 °C(Predicted)
• 密度：
  2.060±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  (4,4-diiodoobut-3-enyl)benzene 在 铜 、 溶剂黄146 、 锌 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.5h， 生成 (4-iodobut-3-enyl)benzene
  参考文献：
  名称：

  从1,1-二碘-1-烯烃立体选择性合成（Z）-1-碘-1-烯烃的简单实用方法

  摘要：

  用Cl 4 / PPh 3由相应的醛制备的1,1-二碘-1-烯烃8用THF / MeOH中的ZnCu/ AcOH处理，得到（Z）-1-碘-1-烯烃9，选择性高产。

  DOI：

  10.1016/j.tetlet.2003.09.166
• 作为产物：
  描述：

  苯丙醛 、 四碘甲烷 在 三苯基膦 作用下， 生成 (4,4-diiodoobut-3-enyl)benzene
  参考文献：
  名称：

  从1,1-二碘-1-烯烃立体选择性合成（Z）-1-碘-1-烯烃的简单实用方法

  摘要：

  用Cl 4 / PPh 3由相应的醛制备的1,1-二碘-1-烯烃8用THF / MeOH中的ZnCu/ AcOH处理，得到（Z）-1-碘-1-烯烃9，选择性高产。

  DOI：

  10.1016/j.tetlet.2003.09.166

文献信息

• Highly Efficient Two-Step Synthesis of C-sp³-Centered Geminal Diiodides
  作者：Jean-Manuel Cloarec、André B. Charette

  DOI：10.1021/ol047997l

  日期：2004.12.1

  [reaction: see text] Trisubstituted gem-diiodoalkenes of functionalized chains are efficiently reduced to the corresponding terminal geminal diiodides in high yields upon treatment with the diazene precursor, diethyl 4-(hydrazinosulfonyl)-benzyl phosphonate.

  [反应：见正文]用重氮二烯前体4-（肼基磺酰基）-苄基膦酸二乙酯处理后，官能化链的三取代的正二碘代烯烃可有效地高产率还原为相应的端基二碘化碘。
• Stereospecific Cross-Coupling of α-(Thiocarbamoyl)organostannanes with Alkenyl, Aryl, and Heteroaryl Iodides
  作者：J. R. Falck、Paresh K. Patel、Anish Bandyopadhyay

  DOI：10.1021/ja064948q

  日期：2007.1.1

  PTC-protected alpha-hydroxystannanes cross-couple with alkenyl/aryl/heteroaryl iodides in moderate to good yields using copper(I) thiophene-2-carboxylate (CuTC) in THF at or below room temperature. Simple aryl iodides and 1-iodocyclohexene, two classes of electrophiles that typically react sluggishly, are also good substrates. Cross-couplings proceed with retention of configuration at the alkenyl-

  在室温或低于室温下，使用 THF 中的噻吩-2-羧酸铜 (CuTC)，外消旋和缩放 PTC 保护的 α-羟基锡烷与烯基/芳基/杂芳基碘化物以中等至良好的产率交叉偶联。简单的芳基碘化物和 1-碘代环己烯是两类通常反应缓慢的亲电子试剂，也是很好的底物。交叉偶联继续保持在烯基和甲锡烷基取代的立体中心的构型。
• Stereoselective Hydrogenolysis of 1,1-Dibromo-1-alkenes and Stereospecific Synthesis of Conjugated (<i>Z</i>)-Alkenyl Compounds
  作者：Jun'ichi Uenishi、Reiko Kawahama、Osamu Yonemitsu、Jiro Tsuji

  DOI：10.1021/jo9812781

  日期：1998.11.1

  The Pd-catalyzed hydrogenolysis of 1,1-dibromoalkenes with Bu3SnH occurs at room temperature stereoselectively to give (Z)-1-bromo-1-alkenes. We sought to determine the optimal reaction conditions and illustrate the scope of this method with 32 dibromoalkenes including alkenyl- and alkynyl-conjugated 1,l-dibromo-l-alkenes 7a-h and 2,2-disubstituted I,1-dibromo-1-alkenes 9a-f. Triphenylphosphine was the best ligand for the Pd-catalyzed hydrogenolysis. A wide range of solvents can be used for this reaction excluding EtOH, AcOH, and CHCl3. However, the reaction proceeds even in these solvents with the addition of a cosolvent or radical scavenger. The reaction of 1,1-diiodo-1-alkene (3) gave a mixture of (Z)-1-iodo-1-alkene (4), (Z)-1-tributylstannyl-1-alkene (5), and a terminal alkene 6, while that of 1,1-dichloroalkene did not occur. This selectivity can be explained by the stereoselective insertion of Pd(0) to a trans bromine-alkenyl carbon bond, successive transmetalation with Bu3SnH, and reductive elimination. The Suzuki and Sonogashira couplings of the resulting (Z)-1-bromo-1-alkenes with alkenyl(dialkoxy)borane and terminal alkyne occurred to give conjugated polyenes and enynes stereospecifically. The Pd-catalyzed hydrogenolysis of 1,l-dibromo-l-alkene and successive cross-coupling can be carried out either in a stepwise manner or in one-pot under the same Pd catalysis. These two processes should be useful for the synthesis of geometrically pure polyene and enyne with a Z-alkenyl unit.
• A simple and practical method for the stereoselective synthesis of (Z)-1-iodo-1-alkenes from 1,1-diiodo-1-alkenes
  作者：Isao Kadota、Hirokazu Ueno、Akio Ohno、Yoshinori Yamamoto

  DOI：10.1016/j.tetlet.2003.09.166

  日期：2003.11

  Treatment of the 1,1-diiodo-1-alkenes 8, prepared from the corresponding aldehydes with CI4/PPh3, with ZnCu/AcOH in THF–MeOH gave the (Z)-1-iodo-1-alkenes 9, selectively, in good yields.

  用Cl 4 / PPh 3由相应的醛制备的1,1-二碘-1-烯烃8用THF / MeOH中的ZnCu/ AcOH处理，得到（Z）-1-碘-1-烯烃9，选择性高产。