2-iodobenzyl vinyl ether | 57056-91-4

• 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: 2-iodobenzyl vinyl ether
• 英文别名: o-iodobenzylvinylether；1-[(ethenoxy)methyl]-2-iodobenzene；1-[(Ethenyloxy)methyl]-2-iodobenzene；1-(ethenoxymethyl)-2-iodobenzene
• CAS: 57056-91-4
• 化学式: C₉H₉IO
• 分子量: 260.074
• InChiKey: UFCYJNABMFHXDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  2-iodobenzyl vinyl ether 在 sodium cobalt(I) N,N'-1,2-ethylenebis(salicylidenimine) 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以34%的产率得到乙烯氧基甲基-苯
  参考文献：
  名称：

  Bhandal, Harcharan; Patel, Vinod F.; Pattenden, Gerald, Journal of the Chemical Society. Perkin transactions I, 1990, # 10, p. 2691 - 2701

  摘要：

  DOI：
• 作为产物：
  描述：

  2-碘苄醇 、 乙烯基乙醚 在 mercury(II) diacetate 作用下， 生成 2-iodobenzyl vinyl ether
  参考文献：
  名称：

  含不饱和原取代基的芳基环化的机理

  摘要：

  由三丁基锡烷与含不饱和邻位取代基的芳基碘化物相互作用而产生的芳基区域特异性地环化，从而提供了对新形成的环外环外包含新形成的自由基中心的产物。已经确定了许多相关基团的相对环化率。该结果与这样的假设相一致：通过半占据的轨道与π*轨道的一个波瓣的主要相互作用形成了用于烯烃键均溶加成的过渡态。

  DOI：

  10.1039/p29750000795

文献信息

• Mechanism of cyclization of aryl radicals containing unsaturated ortho-substituents
  作者：Athelstan L. J. Beckwith、William B. Gara

  DOI：10.1039/p29750000795

  日期：——

  Aryl radicals generated by interaction of tributylstannane with aryl iodides containing unsaturated ortho-substituents cyclize regiospecifically to afford products containing the newly formed-radical centre exocyclic to the newly-formed ring. The relative rates of cyclization of a number of related radicals have been determined. The results are consistent with the hypothesis that the transition state

  由三丁基锡烷与含不饱和邻位取代基的芳基碘化物相互作用而产生的芳基区域特异性地环化，从而提供了对新形成的环外环外包含新形成的自由基中心的产物。已经确定了许多相关基团的相对环化率。该结果与这样的假设相一致：通过半占据的轨道与π*轨道的一个波瓣的主要相互作用形成了用于烯烃键均溶加成的过渡态。
• Selective Approaches to α‐ and β‐Arylated Vinyl Ethers
  作者：Anna Domzalska‐Pieczykolan、Ignacio Funes‐Ardoiz、Bartłomiej Furman、Carsten Bolm

  DOI：10.1002/anie.202109801

  日期：2022.1.3

  Benzyl vinyl ethers have selectively been arylated at either α or β position by fine-tuned Heck-type palladium catalyses. In contrast to previous protocols, no excess of arylating reagent or substrate chelation is necessary. For achieving good yields and high α/β-selectivities various factors determining the catalytic system had to be optimized. The results of DFT computational studies correlate selectivity

  苄基乙烯基醚已通过微调的 Heck 型钯催化剂在 α 或 β 位选择性芳基化。与以前的协议相比，不需要过量的芳基化试剂或底物螯合。为了获得良好的收率和高 α/β-选择性，必须优化决定催化体系的各种因素。DFT 计算研究的结果将选择性与 Pd 中心上的电子丰富度相关联。
• The conversion of 4-oxa-5-hexenyllithiums to 4-alken-1-ols: a novel [1,4]-wittig rearrangement
  作者：William F. Bailey、Lyn M.J. Zarcone

  DOI：10.1016/0040-4039(91)80002-n

  日期：1991.1

  corresponding 3-iodoalkyl vinyl ethers (1) by low-temperature lithium - iodine exchange, rearrange in high yield to 4-alken-1-ols (4) when warmed to room temperature. This transformation, which constitutes a [1,4]-Wittig rearrangement, is mediated by 5-exo-trig closure of 2 to a (2-tetrahydrofuranyl)methyllithium (3) followed by spontaneous ring opening to give 4.

  4-氧杂-5-己烯基锂（2），可以由相应的3-碘烷基乙烯基醚（1）通过低温锂-碘交换制得，并以高收率重排为4-烯-1-醇（4）。当加热到室温时。这种转变，这构成了〔1,4〕-Wittig重排，由5 -外-TRIG的闭合介导2的（2-四氢呋喃基）甲基锂（3然后自然开环），得到4。
• Stable Arylpalladium Iodides and Reactive Arylpalladium Trifluoromethanesulfonates in the Intramolecular Heck Reaction
  作者：John M. Brown、Jesus J. Perez-Torrente、Nathaniel W. Alcock、Howard J. Clase

  DOI：10.1021/om00001a032

  日期：1995.1

  The reactions of 1-iodo-2-(3-butenyl)benzene and of two side-chain ether analogs with [1,1'-bis(diphenylphosphino)ferrocene](eta(2)-cyclooctatetraene)palladium gave the expected (eta(1)-aryl)-(eta(1)-iodo)palldium adducts, the 2-oxa-3-butenyl complex being characterized by X-ray crystallography. The alkene does not interact directly with palladium. Restricted rotation about the aryl-palladium bond was observed on the NMR time scale in all cases, since the methylene group(s) of the side chain were diastereotopic. The complexes were stable, but on treatment with silver trifluoromethanesulfonate in acetone at low temperature an unstable species was identified by H-1 and P-31 NMR in two of the three cases. Spectral observations were consistent with the formation and subsequent rearrangement of an intermediate along the pathway of an intramolecular Heck cyclisation with structure o-C6H4OC(CH3)(Pd[dppf]OTf).
• TENNANT, SHAUN;WEGE, DIETER, J. CHEM. SOC. PERKIN TRANS. PT 1,(1989) N1, C. 2089-2093
  作者：TENNANT, SHAUN、WEGE, DIETER

  DOI：——

  日期：——