2-<(Z)-(3-iodoprop-2-enyl)oxy>tetrahydropyran | 80288-03-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 2-<(Z)-(3-iodoprop-2-enyl)oxy>tetrahydropyran
• 英文别名: (Z)-3-iodo-1-(2-tetrahydro-2H-pyranyloxy)prop-2-ene；(Z)-1-iodo-3-(tetrahydropyran-2-yloxy)prop-1-ene；2-[(Z)-3-iodoprop-2-enoxy]oxane
• CAS: 80288-03-5
• 化学式: C₈H₁₃IO₂
• 分子量: 268.095
• InChiKey: DUHKMASEUMGGST-HYXAFXHYSA-N

物化性质

• 沸点：
  281.2±40.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-<(Z)-(3-iodoprop-2-enyl)oxy>tetrahydropyran 在 双(乙腈)氯化钯(II) 2,4,6-三甲基吡啶 、 甲基磺酰氯 、 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-[(2Z,4E)-6-chlorohexa-2,4-dienoxy]oxane
  参考文献：
  名称：

  Comparative Effects of Conjugated and Deconjugated Isomeric Enones on the Transannular Diels−Alder Reaction

  摘要：

  [GRAPHICS]Two isomeric cyclic trienones 2 and 3 (with four methyl esters at positions 3 and 10) underwent transannular Diels-Alder (TADA) reaction at very different temperatures. This drastic difference could be traced to the capacity of the enone dienophile to be conjugated or unconjugated at the transition state. Molecular modeling could confirm this explanation. The calculated enone proved to be very distorted in transition state ts2, and the TADA reaction temperature was accordingly much higher than the one corresponding to ts3 in which the enone was flat.

  DOI：

  10.1021/ol035791z
• 作为产物：
  描述：

  哌喃 在 正丁基锂 、 碘 、 potassium diazodicarboxylate 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 2.75h， 生成 2-<(Z)-(3-iodoprop-2-enyl)oxy>tetrahydropyran
  参考文献：
  名称：

  Synthesis and intramolecular cycloaddition reactions of some 3-substituted-6-azidohexa-2,4-dienoate esters

  摘要：

  DOI：

  10.1021/jo00343a025

文献信息

• Development of a general copper-catalyzed vinylic Finkelstein reaction—application to the synthesis of the C1–C9 fragment of laingolide B
  作者：Antoine Nitelet、Kévin Jouvin、Gwilherm Evano

  DOI：10.1016/j.tet.2016.07.018

  日期：2016.10

  conditions compatible with a range of highly functionalized substrates. The potential of this vinylic halogen exchange reaction in total synthesis and medicinal chemistry was demonstrated by its successful use for the synthesis of the C1–C9 fragment of laingolide B and for the late-stage modification of drug-like molecules. The extension of this halogen exchange to the acetylenic and allenic Finkelstein

  据报道，铜催化的乙烯基芬克尔斯坦反应的一种有效且广泛适用的方法。使用简单，易于获得且便宜的催化系统，可以将各种烯基碘化物和溴化物平稳地转化为它们的较低同系物，并具有高收率并完全保留双键的几何形状。这种乙烯基Finkelstein反应的关键特征是其广泛的适用性，使易得的链烯基碘化物转化为难得的溴代和氯代对应物，并且温和的反应条件与一系列高度官能化的底物相容。这种乙烯基卤素交换反应在全合成和药物化学中的潜力已通过成功地用于合成Laingolide B的C1-C9片段以及对药物样分子进行后期修饰而得到证明。还报道了这种卤素交换扩展到炔属和烯属的Finkelstein反应。
• A General Copper-Catalyzed Vinylic Halogen Exchange Reaction
  作者：Antoine Nitelet、Gwilherm Evano

  DOI：10.1021/acs.orglett.6b00678

  日期：2016.4.15

  An efficient and general system for the halogen exchange reaction in alkenyl halides has been developed. Upon reaction with catalytic amounts of copper iodide and trans-N,N′-dimethylcyclohexane-1,2-diamine in the presence of tetramethylammonium chloride or bromide, a wide range of easily accessible alkenyl iodides can be smoothly transformed to their far less available chlorinated and brominated derivatives

  已经开发了用于链烯基卤化物中的卤素交换反应的有效且通用的系统。在与催化量的碘化铜和反应反式- ñ，Ñ在四甲基氯化铵或溴化铵，宽范围容易获得烯基碘化物的存在'N'-二甲基-1,2-二胺能够顺利地转化为它们的远较少可用氯化和溴化衍生物，具有极高的收率并完全保留了双键的几何形状。该反应还能够使溴代烯烃氯化，并且可以扩展到宝石-二溴代烯烃的使用。
• Stephens-Castro-Coupling of Halogenated Vinylic and Allylic Silanes with (Homo-)Propargylic Compounds
  作者：Jazid Kabbara、Christoph Hoffmann、Dieter Schinzer

  DOI：10.1055/s-1995-3903

  日期：1995.3

  Vinyl halides containing vinylic and allylic silane terminators undergo a stereospecific palladium(0)-catalyzed cross-coupling with derivatives of terminal propargylic and homopropargylic alcohols to polyunsaturated silanes. Basic stable and unstable protecting groups were tolerated under slightly different reaction conditions.

  含有维烯和烯丙基硅烷终止剂的氯化乙烯在轻微不同的反应条件下，能够与末端丙炔醇和同丙炔醇的衍生物进行立体选择性的钯(0)催化交叉偶联，生成多不饱和硅烷。基本的稳定和不稳定保护基团在此反应中均可接受。
• An Efficient Synthesis of a Cyclic Ether Key Intermediate for 9-Membered Masked Enediyne Using an Automated Synthesizer
  作者：Yoshikazu Tanaka、Shinichiro Fuse、Hiroshi Tanaka、Takayuki Doi、Takashi Takahashi

  DOI：10.1021/op9002455

  日期：2009.11.20

  Naturally occurring antibiotics containing 9-membered enediynes have received considerable attention for many years due to their potent DNA-cleaving activity. We previously reported the design and synthesis of a synthetic, masked 9-membered enediyne that possesses DNA-cleaving activity. Despite the importance of the 9-membered enediynes, application of these molecules is limited by their difficult

  含有9元烯二炔的天然存在的抗生素由于其强大的DNA裂解活性而受到了很多年的关注。我们之前报道了具有DNA裂解活性的合成的，掩蔽的9元二烯二炔的设计和合成。尽管9元烯二炔很重要，但这些分子的应用受到合成困难的限制。在本文中，我们报告了一种改进的方法，用于生产合成的，蒙版的9元二烯二炔，该工艺使用自动合成仪生产关键的合成中间体。
• Continuous Flow Chlorination of Alkenyl Iodides Promoted by Copper Tubing
  作者：Antoine Nitelet、Vanessa Kairouz、Hélène Lebel、André Charette、Gwilherm Evano

  DOI：10.1055/s-0037-1610398

  日期：2019.1

  Abstract A simple continuous flow synthesis of alkenyl chlorides from the corresponding readily available alkenyl iodides in copper reactor tubing is described. A variety of alkenyl chlorides were obtained in good to excellent yields with full retention of the double bond geometry. The reaction time was reduced by a factor of 24–48 compared to the batch process. A simple continuous flow synthesis of alkenyl

  摘要 描述了在铜反应器管道中由相应的易得的烯基碘化物简单连续地合成烯基氯化物的方法。以良好至优异的产率获得了各种烯基氯化物，并完全保留了双键的几何形状。与分批处理相比，反应时间减少了24–48倍。 描述了在铜反应器管道中由相应的易得的烯基碘化物简单连续地合成烯基氯化物的方法。以良好至优异的产率获得了各种烯基氯化物，并完全保留了双键的几何形状。与分批处理相比，反应时间减少了24–48倍。