4-iodobenzyl acetate | 90347-65-2

• 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-iodobenzyl acetate
• 英文别名: 4-Iodobenzyl alcohol, acetate；(4-iodophenyl)methyl acetate
• CAS: 90347-65-2
• 化学式: C₉H₉IO₂
• 分子量: 276.074
• InChiKey: VKZHEYVXPIMRCG-UHFFFAOYSA-N

物化性质

• 熔点：
  46-47 °C
• 沸点：
  148-149 °C(Press: 10 Torr)
• 密度：
  1.680±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-iodobenzyl acetate 在 platinum(IV) oxide 、 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 Acetic acid 4-((E)-2-triethylsilanyl-hept-1-enyl)-benzyl ester
  参考文献：
  名称：

  Platinum Oxide Catalyzed Hydrosilylation of Unsymmetrical Internal Aryl Alkynes under Ortho-Substituent Regiocontrol

  摘要：

  [GRAPHICS]PtO2- and H2PtCl6-catalyzed hydrosilylation of internal aryl alkynes having a para or an ortho substituent with triethylsilane are discussed and compared. The regioselectivity of the H-Si bond addition was found to be controlled by the ortho substituent rather than the nature of the platinum catalyst. Arylallcynes with an ortho substituent, regardless of its electronic nature, directed the silyl substituent mainly to the a-position. PtO2 proved to be a versatile and powerful catalyst compared to H2PtCl6 since it prevents the alkyne reduction.

  DOI：

  10.1021/ol052245s
• 作为产物：
  描述：

  4-碘苄基溴 、 potassium acetate 在 溶剂黄146 作用下， 生成 4-iodobenzyl acetate
  参考文献：
  名称：

  Tommila, Annales Academiae Scientiarum Fennicae, Series A, 1942, vol. 59, # 4, p. 3,4

  摘要：

  DOI：

文献信息

• Consequent Construction of C–C and C–N Bonds via Palladium-Catalyzed Dual C–H Activation: Synthesis of Benzo[<i>c</i>]cinnoline Derivatives
  作者：Hongsheng Li、Junhao Zhao、Songjian Yi、Kongzhen Hu、Pengju Feng

  DOI：10.1021/acs.organomet.0c00800

  日期：2021.4.12

  A highly efficient palladium-catalyzed cascade annulation of pyrazolones and aryl iodides to access various benzo[c]cinnoline derivatives has been achieved at 80 °C. A pyridine-type ligand could improve the reaction efficiency under current reaction conditions, giving a higher product yield up to 94%. This novel approach provided a one-pot dual C–H activation strategy with good functional group tolerance

  在80°C时，已经实现了高效的钯催化吡唑啉酮和芳基碘的级联环化反应，以得到各种苯并[ c ]肉桂酸衍生物。吡啶类配体可提高当前反应条件下的反应效率，最高收率可达94％。这种新颖的方法提供了具有良好官能团耐受性的一锅双C–H活化策略，例如卤素，甲氧基，硝基，酯，苯酚等。该产物可以很容易地转化为cinnoline衍生物。
• Engaging sulfinate salts <i>via</i> Ni/photoredox dual catalysis enables facile C_sp2–SO₂R coupling
  作者：María Jesús Cabrera-Afonso、Zhi-Peng Lu、Christopher B. Kelly、Simon B. Lang、Ryan Dykstra、Osvaldo Gutierrez、Gary A. Molander

  DOI：10.1039/c7sc05402e

  日期：——

  employed to prepare sulfones with biological relevance (e.g., in bioconjugation, drug substance synthesis, etc.) as demonstrated in the synthesis of drug-like compounds or their precursors. When paired with existing Ni/photoredox chemistry for Csp3–Csp2 cross-coupling, an array of diverse sulfone scaffolds can be readily assembled from bifunctional electrophiles. A mechanistic manifold consistent with

  该报告详细介绍了通过镍/光氧化还原双重催化构建芳基和杂芳基砜的策略的开发和实施。使用芳基亚磺酸盐，可以在室温、无碱条件下形成C-S键。一系列芳基卤化物和杂芳基卤化物与该方法兼容。所描述的反应的广泛耐受性和温和性质可以潜在地用于制备具有生物相关性的砜（例如，在生物共轭、药物物质合成等中），如在药物样化合物或其前体的合成中所证明的。当与现有的用于 C sp 3 –C sp 2交叉偶联的 Ni/光氧化还原化学配对时，可以很容易地从双功能亲电子试剂组装一系列不同的砜支架。提出了与实验和计算数据一致的机械流形。
• Sonogashira coupling reactions in biodegradable ionic liquids derived from nicotinic acid
  作者：Jitendra R. Harjani、Theodore J. Abraham、Alwyn T. Gomez、M. Teresa Garcia、Robert D. Singer、Peter J. Scammells

  DOI：10.1039/b919394d

  日期：——

  The biodegradable ionic liquids, 3-butoxycarbonyl-1-methylpyridinium bis(trifluoromethanesulfonyl)imides (1a–d), have been evaluated as solvents for copper- and phosphine-free Sonogashira coupling reactions. The stability of these ionic liquids toward basic conditions was analysed in order to further probe their utility for transition metal catalyzed reactions which require the presence of a base.

  可生物降解的离子液体3-丁氧基羰基-1-甲基吡啶双（三氟甲磺酰基）酰亚胺（1a–d）的评估为溶剂 为了 铜- 和 膦-自由的 Sonogashira联轴器反应。为了进一步分析这些离子液体在碱性条件下的稳定性，探测 它们可用于需要碱存在的过渡金属催化反应。
• Palladium-Catalyzed Carbonylative Coupling of Tributyl(1-fluorovinyl)stannane with Aryl Halides and Aryl Triflates
  作者：Takeshi Hanamoto、Kumiko Handa、Tomonori Mido

  DOI：10.1246/bcsj.75.2497

  日期：2002.11

  catalytic amount of CsF in DMF in good yields. The palladium-catalyzed carbonylative cross-coupling reaction of 2 with aryl iodides bearing various functional groups smoothly proceeded giving the corresponding aryl 1-fluorovinyl ketones in good yields under an atmospheric pressure of carbon monoxide. A similar carbonylative cross-coupling reaction of 2 with aryl triflates was also accomplished in the presence

  我们发现三丁基（1-氟乙烯基）锡烷（2）可以很容易地由（1-氟乙烯基）甲基二苯基硅烷1（1）和双（三丁基锡）氧化物在DMF中催化量的CsF存在下反应制备产量。钯催化的 2 与带有各种官能团的芳基碘化物的羰基化交叉偶联反应顺利进行，在一氧化碳的大气压下以良好的产率得到相应的芳基 1-氟乙烯基酮。2 与芳基三氟甲磺酸酯的类似羰基化交叉偶联反应也在四丁基碘化铵 (Bu4NI) 作为添加剂的存在下完成。
• Cross-Coupling Reactions of (1-Fluorovinyl)methydiphenylsilane¹ with Aryl Halides and Aryl Triflates
  作者：Takeshi Hanamoto、Tomoko Kobayashi

  DOI：10.1021/jo030111r

  日期：2003.8.1

  of functional groups (nitro, ester, ketone, and ether) on the aromatic rings can be tolerated under these mild conditions. Aryl iodides are superior to aryl bromides as the coupling reaction partner. The cross-coupling reaction of 1 with aryl triflates instead of aryl halides was also accomplished in the presence of tetrabutylammonium iodide (n-Bu(4)NI) as the additive under similar conditions.

  研究了（1-氟乙烯基）甲基二苯基硅烷（1）与芳基卤化物和芳基三氟甲磺酸酯的氟化铯（CsF）辅助交叉偶联反应。与芳基碘化物的反应平稳进行，在非质子极性溶剂（例如DMF，DMI，DMA和DFA）中，在催化量的CuI和Pd（PPh（3））（4）存在的情况下，提供了相应的（1-氟乙烯基）芳烃。 NMP产量高。在这些温和条件下，可以容忍芳香环上的各种官能团（硝基，酯，酮和醚）。作为偶联反应伙伴，芳基碘化物优于芳基溴化物。在存在四丁基碘化铵（n-Bu（4）NI）作为添加剂的情况下，在相似的条件下，也完成了1与芳基三氟甲磺酸酯而不是芳基卤化物的交叉偶联反应。