1-iodohexa-3,4-diene | 32368-21-1

• 分子结构分类: 有机化合物 - 有机卤素化合物
• 英文名称: 1-iodohexa-3,4-diene
• 英文别名: 6-iodo-2,3-hexadiene；6-iodohexa-2,3-diene；6-iodohexa-1,2-diene
• CAS: 32368-21-1
• 化学式: C₆H₉I
• 分子量: 208.042
• InChiKey: ZQHHKXLGEVFRRY-UHFFFAOYSA-N

物化性质

• 沸点：
  177.1±10.0 °C(Predicted)
• 密度：
  1.500±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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-iodohexa-3,4-diene 在 吡啶 、 lithium aluminium tetrahydride 、 正丁基锂 、 碘 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 170.5h， 生成 2-(prop-1-ynyl)-1-(p-tolylsulfonyl)piperidine
  参考文献：
  名称：

  Davies, Ian W.; Shaw, Robert W.; Wisedale, Richard, Journal of the Chemical Society. Perkin transactions I, 1994, # 24, p. 3557 - 3562

  摘要：

  DOI：
• 作为产物：
  描述：

  hexa-3,4-dienyl tosylate 在 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 72.0h， 以64%的产率得到1-iodohexa-3,4-diene
  参考文献：
  名称：

  Davies, Ian W.; Shaw, Robert W.; Wisedale, Richard, Journal of the Chemical Society. Perkin transactions I, 1994, # 24, p. 3557 - 3562

  摘要：

  DOI：

文献信息

• A silicon-tethered allenic Pauson–Khand reaction
  作者：Kay M. Brummond、Peter C. Sill、Brenden Rickards、Steven J. Geib

  DOI：10.1016/s0040-4039(02)00633-0

  日期：2002.5

  This manuscript describes a silicon-tethered Pauson–Khand reaction and subsequent cleavage of the resulting vinyl silane to afford functionalized alkylidene cyclopentenones. Altering the reaction conditions affords a selective reaction with either π-bond of the allene.

  该手稿描述了硅拴的Pauson-Khand反应以及随后裂解所得的乙烯基硅烷以提供官能化的亚烷基环戊烯酮的方法。改变反应条件提供了与丙二烯的π键的选择性反应。
• Microwave-Assisted Intramolecular [2 + 2] Allenic Cycloaddition Reaction for the Rapid Assembly of Bicyclo[4.2.0]octa-1,6-dienes and Bicyclo[5.2.0]nona-1,7-dienes
  作者：Kay M. Brummond、Daitao Chen

  DOI：10.1021/ol051115g

  日期：2005.8.1

  [2 + 2] cycloaddition reaction. This cycloaddition provides an efficient route to bicyclomethylenecyclobutenes. The reaction occurs with complete regioselectivity for the distal double bond of the allene for the selective formation of a variety of hetero- and carbocyclic substrates. Bicyclo[4.2.0]octadienes and bicyclo[5.2.0]nonadienes have been prepared in high yield. [reaction: see text]

  炔基丙二烯的微波辐射提供分子内[2 + 2]环加成反应。这种环加成反应提供了通往双环亚甲基环丁烯的有效途径。该反应对丙二烯的远端双键具有完全的区域选择性，从而选择性形成了各种杂环和碳环底物。高产率地制备了双环[4.2.0]辛二烯和双环[5.2.0]壬二烯。[反应：看文字]
• A General Synthetic Route to Differentially Functionalized Angularly and Linearly Fused [6−7−5] Ring Systems: A Rh(I)-Catalyzed Cyclocarbonylation Reaction
  作者：Kay M. Brummond、Daitao Chen、Matthew M. Davis

  DOI：10.1021/jo8007258

  日期：2008.7.1

  Investigations of a Rh(I)-catalyzed cyclocarbonylation reaction reveal its general synthetic utility for accessing highly functionalized tricyclic [6-7-5] linear and angular ring systems from allene-ynes. Three types of allene-ynes were prepared and subjected to Rh(I)-catalyzed cyclocarbonylation conditions. For three series of allene-ynes, the [6-7-5] ring systems were afforded in varying yields depending on the substrate structure. One series of allene-ynes afforded the [6-6-5] ring system possessing an alpha-alkylidene cyclopentenone as a result of a selective reaction with the proximal double bond of the allene.
• An Allenic Pauson−Khand-Type Reaction:  A Reversal in π-Bond Selectivity and the Formation of Seven-Membered Rings
  作者：Kay M. Brummond、Hongfeng Chen、Kimberly D. Fisher、Angela D. Kerekes、Brenden Rickards、Peter C. Sill、Steven J. Geib

  DOI：10.1021/ol025955w

  日期：2002.5.1

  [GRAPHICS]Treatment of alkynyl allenes with [Rh(CO)(2)Cl](2) results in a formal [2 + 2 + 1] cycloaddition reaction. This reaction occurs with complete regioselectivity for a variety of substrates affording only 4-alkylidene cyclopentenones in good yields. Moreover, seven-membered rings have been prepared in high yields.
• Stereochemistry of solvolytic displacement at vinyl carbon. Reactions of 1-cyclopropyl-2-methylvinyl cations formed on silver-catalyzed ionization of cis- and trans-1-cyclopropyl-1-iodopropenes and 3,4-hexadien-1-yl iodide
  作者：Robert G. Bergman、Donald R. Kelsey

  DOI：10.1021/ja00737a017

  日期：1971.4