2-(2-碘乙炔基)萘 | 223758-79-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2-(2-碘乙炔基)萘
• 英文名称: 2-naphthylethynyl iodide
• 英文别名: 2-(iodoethynyl)naphthalene；2-(2-iodoethynyl)naphthalene
• CAS: 223758-79-0
• 化学式: C₁₂H₇I
• 分子量: 278.092
• InChiKey: RVNRFAGEFSGZIU-UHFFFAOYSA-N

物化性质

• 沸点：
  346.6±15.0 °C(Predicted)
• 密度：
  1.73±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  2-(2-碘乙炔基)萘 在 溴 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以83%的产率得到2-naphthyl-1,2-dibromoethynyl iodide
  参考文献：
  名称：

  Synthesis and Properties of Copper, Mercury, and Silver (2-Naphthyl)acetylenides

  摘要：

  (Z)-2-Naphthylacetylene was synthesized by the reaction of (Z)-3-(2-naphthyl)-3-chloropropenal (prepared from 2-acetylnaphthalene) with aqueous NaOH in dioxane. The reactions of 2-naphthylacetylene with CuCl, [Ag(NH3)(2)]NO3, and K-2[HgI4] gave copper, silver, and mercury 2-naphthylacetylenides, respectively. Silver naphthylacetylenide reacts with iodine to give the iodoethynyl derivative, which readily takes up bromine across the triple bond.

  DOI：

  10.1023/b:rugc.0000031860.91216.62
• 作为产物：
  描述：

  silver 2-naphthylacetylenide 在 碘 作用下， 以 氯仿 为溶剂， 以91%的产率得到2-(2-碘乙炔基)萘
  参考文献：
  名称：

  Synthesis and Properties of Copper, Mercury, and Silver (2-Naphthyl)acetylenides

  摘要：

  (Z)-2-Naphthylacetylene was synthesized by the reaction of (Z)-3-(2-naphthyl)-3-chloropropenal (prepared from 2-acetylnaphthalene) with aqueous NaOH in dioxane. The reactions of 2-naphthylacetylene with CuCl, [Ag(NH3)(2)]NO3, and K-2[HgI4] gave copper, silver, and mercury 2-naphthylacetylenides, respectively. Silver naphthylacetylenide reacts with iodine to give the iodoethynyl derivative, which readily takes up bromine across the triple bond.

  DOI：

  10.1023/b:rugc.0000031860.91216.62

文献信息

• Iron(III) Chloride/Dialkyl Diselenides‐Promoted Cascade Cyclization of <i>ortho</i> ‐Diynyl Benzyl Chalcogenides
  作者：Roberto do Carmo Pinheiro、Davi F. Back、Gilson Zeni

  DOI：10.1002/adsc.201900086

  日期：2019.4.16

  Treatment of ortho‐diynyl benzyl chalcogenides with a mixture of iron(III) chloride and diorganyl diselenides led to functionalized chalcogen isochromene‐fused chalcogenophene derivatives. The reaction parameters were studied and the results indicated that the reaction of ortho‐ diynyl benzyl chalcogenides (0.25 mmol) with iron(III) chloride hexahydrate (2.0 equiv.) and diorganyl diselenide (2 equiv

  用氯化铁（III）和二有机基二硒化物的混合物处理邻二炔基苄基硫属元素化物，导致官能化的硫属元素异色烯稠合的硫属元素衍生物。研究了反应参数，结果表明，在二氯乙烷回流下，邻二炔基苄硫属元素化物（0.25 mmol）与六水合氯化铁（III）（2.0当量）和二有机二硒化物（2当量）反应是最佳条件。使产品的收率达到40-83％。结果支持这样的想法，即铁盐和二有机二硒化物的混合物具有双重作用，促进了环化作用，并在异二十碳五烯色素的3位引入了新的功能化。该方法具有高度的区域选择性，可通过6- endo获得产品-Dig模式经由5-继之以第二环化内切-Dig模式。
• Reaction of 1-iodoalkynes with allylzirconiums: Generation of alkylidene carbenoid via allylzirconation
  作者：Shigeo Yamanoi、Takashi Matsumoto、Keisuke Suzuki

  DOI：10.1016/s0040-4039(99)00296-8

  日期：1999.4

  Allylzirconium species, generated by hydrozirconation of allenes, react with 1-iodoalkynes in the presence of methylaluminoxane (MAO) to give the substitution products of the iodide by an allyl group. Labelling study for 2-(iodoethynyl)naphthalene suggested that the reaction involves allylzirconation of iodoalkynes to generate an alkylidene carbenoid that undergoes 1,2-rearrangement.

  通过烯丙基加氢锆化生成的烯丙基锆物种在甲基铝氧烷（MAO）存在下与1-碘代炔烃反应，生成烯丙基的碘化物取代产物。对2-（碘乙炔基）萘的标记研究表明，该反应涉及碘代炔烃的烯丙基锆化反应，生成经过1,2-重排的亚烷基类胡萝卜素。
• Ti-catalyzed regioselective ring-opening alkynylation of epoxides with haloalkynes
  作者：Di Zhang、Hao Li、Dong Yi、Shijing Tu、Zhongyu Qi、Siping Wei、Qiang Fu、Haiyan Fu、Xi Du

  DOI：10.1016/j.tetlet.2021.153461

  日期：2021.11

  Ti-catalyzed ring-opening alkynylation of epoxides with haloalkynes has been achieved, allowing an efficient and regioselective entry to various propargylic alcohols in moderate to good yields. The developed protocol features extremely mild reaction conditions, broad substrate scope, varied functional group compatibility, and chemospecificity in the rearrangements of epoxides to aldehydes.

  已经实现了环氧化物与卤代炔烃的 Ti 催化开环炔基化，允许以中等至良好的产率有效和区域选择性地进入各种炔丙醇。开发的协议具有极其温和的反应条件、广泛的底物范围、不同的官能团兼容性以及环氧化物重排为醛的化学特异性。
• Stereoselective synthesis of <i>E</i>-3-(arylmethylidene)-5-(alkyl/aryl)-2(3<i>H</i>)-furanones by sequential hydroacyloxylation-Mizoroki–Heck reactions of iodoalkynes
  作者：Gopinathan Muthusamy、Sunil V. Pansare

  DOI：10.1039/c8ob02063a

  日期：——

  stereoselective synthesis of E-3-(arylidene)-5-(alkyl/aryl)-2(3H)-furanones was developed. The methodology features regioselective addition of β-aryl acrylic acids to iodoacetylenes to furnish the Z-acyloxy iodoalkenes. A stereoselective 5-exo-trig Mizoroki–Heck reaction of the acyloxy iodoalkenes generates the target E-2(3H)-furanones. The approach was applied in a formal synthesis of the naturally

  开发了模块化的E -3-（亚芳基）-5-（烷基/芳基）-2（3 H）-呋喃酮的立体选择性合成方法。该方法的特征在于将β-芳基丙烯酸的区域选择性加成到碘乙炔中以提供Z-酰氧基碘烯烃。酰氧基碘代烯烃的立体选择性5 -exo-trig Mizoroki-Heck反应生成目标E -2（3 H）-呋喃酮。该方法被用于天然存在的激酶抑制剂BE-23372M的正式合成中。
• Unlocking Migratory Insertion in Gold Redox Catalysis
  作者：Wenliang Wang、Meiling Ding、Chuan‐Gang Zhao、Shuai Chen、Chengjian Zhu、Jie Han、Weipeng Li、Jin Xie

  DOI：10.1002/anie.202304019

  日期：2023.7.17

  Exploration of elementary reactions in organometallic catalysis is an important method with which to discover new reactions. In this article, we report a gold(I)‐catalyzed iodo‐alkynylation of benzyne involving the merging of challenging migratory insertion and an oxidative addition process in gold catalytic cycle. A wide range of structurally diverse alkynyl iodides are good coupling partners in this iodo‐alkynylation transformation. Both aliphatic and aromatic alkynyl iodides can react with benzynes smoothly to afford highly functionalized 1,2‐disubstituted aromatics in moderate to good yields. Its good functional group compatibility and late‐stage application of complex molecules demonstrate its synthetic robustness. Studies of the mechanism reveals the feasibility of oxidative addition and the DFT calculations demonstrate the possible migratory insertion of benzyne into Au^III‐carbon bonds in the Au^I/Au^III redox catalytic cycle, representing an important step towards an elementary reaction in gold chemistry research.

  摘要 探索有机金属催化中的基本反应是发现新反应的重要方法。本文报告了一种金（I）催化的苄基碘炔化反应，涉及金催化循环中具有挑战性的迁移插入和氧化加成过程的合并。在这种碘-炔基转化过程中，多种结构不同的炔基碘化物都是很好的偶联剂。脂肪族和芳香族炔基碘化物都能与苄基化合物顺利发生反应，以中等至良好的收率得到高度官能化的 1,2-二取代芳烃。其良好的官能团兼容性和复杂分子的后期应用证明了它的合成稳定性。对其机理的研究揭示了氧化加成的可行性，而 DFT 计算则证明了在 AuI/AuIII 氧化还原催化循环中，苄基可能会迁移插入 AuIII 碳键，这代表着向金化学研究的基本反应迈出了重要的一步。