(E)-1-(benzyloxy)-4-(2-iodovinyl)benzene | 1085710-20-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-1-(benzyloxy)-4-(2-iodovinyl)benzene
• 英文别名: 1-[(E)-2-iodoethenyl]-4-phenylmethoxybenzene
• CAS: 1085710-20-8
• 化学式: C₁₅H₁₃IO
• 分子量: 336.172
• InChiKey: BTAWSHXAQMCKNS-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-1-(benzyloxy)-4-(2-iodovinyl)benzene 、 4,8-bis(benzyloxy)quinoline-2-carboxamide 在 copper(I) oxide 、 caesium carbonate 、 N,N'-二甲基乙二胺 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以82%的产率得到(E)-4,8-bis(benzyloxy)-N-(4-(benzyloxy)styryl)quinoline-2-carboxamide
  参考文献：
  名称：

  Synthesis of Perspicamide A and Related Diverse Analogues: Their Bioevaluation as Potent Antileishmanial Agents

  摘要：

  The first protocol for the synthesis of perspicamide A and related diverse analogues has been developed from economical and readily available starting materials. Furthermore, a few synthesized analogues, 24a, 246, 24c, 24d, and 241, exhibited potent activity against Leishmania donovani with IC50 values ranging from 3.75 to 10.37 mu M and a selectivity index (SI) ranging from 9.58 to 53.12, which is improved compared to the standard drug Miltefosine (IC50 12.4 mu M and SI 4.1).

  DOI：

  10.1021/jo3025626
• 作为产物：
  描述：

  4-苯甲氧基苯乙酮 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 二苯基甲氧基膦 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 7.51h， 生成 (E)-1-(benzyloxy)-4-(2-iodovinyl)benzene
  参考文献：
  名称：

  铑催化酮的脱氧和硼酸化：结合实验和理论研究

  摘要：

  已经开发了铑催化的酮与 B2pin2 的脱氧和硼酸化，从而有效地形成烯烃、乙烯基硼酸酯和乙烯基二硼酸酯。这些反应的特点是反应条件温和，底物范围广，官能团兼容性好。机理研究支持酮最初经过 Rh 催化脱氧以通过硼烯醇化物中间体得到烯烃，随后 Rh 催化的烯烃脱氢硼化导致乙烯基硼酸酯和二硼化产物的形成，这也得到 DFT 计算的支持。

  DOI：

  10.1021/jacs.0c07854

文献信息

• Synthesis of 2-Substituted Pyrazolo[1,5-<i>a</i>]pyridines through Cascade Direct Alkenylation/Cyclization Reactions
  作者：James J. Mousseau、Angélique Fortier、André B. Charette

  DOI：10.1021/ol902710f

  日期：2010.2.5

  from N-iminopyridinium ylides is described. These medicinally interesting compounds are formed through a cascade process involving a palladium-catalyzed direct alkenylation reaction followed by silver-mediated cyclization. The reaction can be performed with a wide range of electron-poor and electron-rich alkenyl iodides in good yields. This work represents perhaps the most direct route for the preparation

  描述了由N-亚氨基吡啶鎓的叶立德合成2-取代的吡唑并[1，5- a ]吡啶。这些医学上有趣的化合物是通过级联过程形成的，该过程涉及钯催化的直接烯基化反应，然后进行银介导的环化反应。该反应可与多种贫电子和富电子的烯基碘化物以高收率进行。这项工作可能代表了制备这些化合物的最直接途径。
• Intermolecular Pauson–Khand-Type Reaction of Vinyl Iodides with Alkynes and a CO Surrogate
  作者：Philip Boehm、Elliott H. Denton、Joel Wick、Bill Morandi

  DOI：10.1021/acs.joc.2c02465

  日期：——

  three-component reaction utilizes vinyl iodides and internal alkynes to form the carbon framework of the cyclopentenone with Cr(CO)6 serving as an easy to handle, solid CO surrogate, and a hydrosilane as a hydride source. We demonstrate the scope of the reaction which includes a wide range of functional groups. The reaction is regioselective, with the use of linear or branched vinyl iodides resulting in

  报道了一种钯催化的多取代环戊烯酮分子间合成策略。三组分反应利用乙烯基碘化物和内部炔烃形成环戊烯酮的碳骨架，其中 Cr(CO) 6作为易于处理的固体 CO 替代物，氢硅烷作为氢化物源。我们展示了反应的范围，其中包括范围广泛的官能团。该反应具有区域选择性，使用直链或支链乙烯基碘化物分别生成 α- 或 β- 取代的环戊烯酮。此外，我们表明，通过形成乙烯基碘和随后的 Pauson-Khand 型反应，可以使用市售炔烃的两步序列来生成环戊烯酮产品。
• Synthesis of 2- and 2,3-Substituted Pyrazolo[1,5-<i>a</i>]pyridines: Scope and Mechanistic Considerations of a Domino Direct Alkynylation and Cyclization of <i>N</i>-Iminopyridinium Ylides Using Alkenyl Bromides, Alkenyl Iodides, and Alkynes
  作者：James J. Mousseau、James A. Bull、Carolyn L. Ladd、Angélique Fortier、Daniela Sustac Roman、André B. Charette

  DOI：10.1021/jo201303x

  日期：2011.10.21

  Direct functionalization and tandem processes have both received considerable recent interest due to their cost and time efficiency. Herein we report the synthesis of difficult to obtain 2-substituted pyrazolo[1,5-a]pyridines through a tandem palladium-catalyzed/silver-mediated elimination/direct functionalization/cyclization reaction involving N-benzoyliminopyridinium ylides. As such, these biologically important molecules are prepared in an efficient, high-yielding manner, only requiring a two-step sequence from pyridine. Aryl-substituted alkenyl bromides and iodides are effective ylide coupling partners. Mechanistic studies led to the use of terminal alkynes, which extended the scope of the reaction to include alkyl substitution on the unsaturated reactive site. The optimization, scope, and mechanistic considerations of the process are discussed.
• Bull, James A.; Mousseau, James J.; Charette, Andre B., Organic Letters, 2008, vol. 10, # 23, p. 5484 - 5488
  作者：Bull, James A.、Mousseau, James J.、Charette, Andre B.

  DOI：——

  日期：——