-(1-iodo-2-(phenylsulfonyl)vinyl)benzene

• 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: -(1-iodo-2-(phenylsulfonyl)vinyl)benzene
• 英文别名: [2-(Benzenesulfonyl)-1-iodoethenyl]benzene；[2-(benzenesulfonyl)-1-iodoethenyl]benzene
• 化学式: C₁₄H₁₁IO₂S
• 分子量: 370.211
• InChiKey: JZLJCCYOXIAOGM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.89
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  -(1-iodo-2-(phenylsulfonyl)vinyl)benzene 在 potassium carbonate 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 5.0h， 生成 dimethyl (phenylethynyl)phosphonate
  参考文献：
  名称：

  Recognition Characteristics of an Adaptive Vesicular Assembly of Amphiphilic Baskets for Selective Detection and Mitigation of Toxic Nerve Agents

  摘要：

  We used isothermal titration calorimetry to investigate the affinity of basket 1 (470 Å(3)) for trapping variously sized and shaped organophosphonates (OPs) 2-12 (137-244 Å(3)) in water at 298.0 K. The encapsulation is, in each case, driven by favorable entropy (TΔS° = 2.9 kcal/mol), while the enthalpic component stays small and in some cases endothermic (ΔH° ≥ -1 kcal/mol). Presumably, a desolvation of basket 1 and OP guests permits the inclusion complexation at room temperature via a "classical" hydrophobic effect. The amphiphilic basket 1 shows a greater affinity (ΔG° ≈ -5 to -6 kcal/mol), both experimentally and computationally, for encapsulating larger organophosphonates whose size and shape correspond to VX-type agents (289 A(3)). Importantly, baskets assemble into a vesicular nanomaterial (DH ≈ 350 nm) that in the presence of neutral OP compounds undergoes a phase transition to give nanoparticles (DH ≈ 250 nm). Upon the addition of an anionic guest to basket 1, however, there was no formation of nanoparticles and the vesicles grew into larger vesicles (DH ≈ 750 nm). The interconversion of the different nanostructures is reversible and, moreover, a function of the organophosphonate present in solution. On the basis of (1)H NMR spectroscopic data, we deduced that neutral guests insert deep into the basket's cavity to change its shape and thereby promote the conversion of vesicles into nanoparticles. On the contrary, the anionic guests reside at the northern portion of the host to slightly affect its shape and geometric properties, thereby resulting in the vesicles merely transforming into larger vesicles.

  DOI：

  10.1021/ja510477q
• 作为产物：
  描述：

  sodium benzenesulfonate 、 苯乙炔 在 ammonium cerium (IV) nitrate 、 sodium iodide 作用下， 以 乙腈 为溶剂， 生成 -(1-iodo-2-(phenylsulfonyl)vinyl)benzene
  参考文献：
  名称：

  通过可见光诱导的自由基级联反应从色胺直接合成 C3-炔基吡咯并二氢吲哚

  摘要：

  开发了一种可见光诱导的自由基级联反应，用于色胺与炔基砜的直接炔基化，以优异的收率提供了一系列 C3-炔基吡咯并二氢吲哚。该方法具有现成的底物、良好的官能团耐受性和可扩展性。C3-炔基吡咯并二氢吲哚在制备复杂且有价值的吡咯并二氢吲哚生物碱方面显示出作为有用结构单元的巨大潜力。

  DOI：

  10.1039/d2cc05905c

文献信息

• Consecutive visible-light photoredox decarboxylative couplings of adipic acid active esters with alkynyl sulfones leading to cyclic compounds
  作者：Jingjing Li、Hua Tian、Min Jiang、Haijun Yang、Yufen Zhao、Hua Fu

  DOI：10.1039/c6cc04386k

  日期：——

  active esters (bis(1,3-dioxoisoindolin-2-yl)-substituted hexanedioates) with substituted 1-(2-arylethynylsulfonyl)benzenes have been developed under visible-light photocatalysis. The successive photoredox decarboxylative C-C bond formation...

  在可见光光催化下，己二酸活性酯（双（1，3-二氧代异吲哚啉-2-基）取代的己二酸酯）与取代的1-（2-芳基乙炔基磺酰基）苯的新型高效连续光氧化还原脱羧偶联已得到开发。连续的光氧化还原脱羧CC键的形成...
• Visible-light photoredox synthesis of internal alkynes containing quaternary carbons
  作者：Chang Gao、Jingjing Li、Jipan Yu、Haijun Yang、Hua Fu

  DOI：10.1039/c6cc01632d

  日期：——

  A novel and efficient visible-light photoredox method for synthesis of internal alkynes containing quaternary carbons has been developed via couplings of N-phthalimidoyl oxalates of tert-alcohols with 1-(2-(arylsulfonyl)ethynyl)benzenes. The reactions were...

  通过叔醇的N-邻苯二甲酰亚胺基草酸酯与1-（2-（芳基磺酰基）乙炔基）苯的偶联，已开发出一种新颖且有效的可见光光氧化还原方法，用于合成含有季碳的内部炔烃。反应是...
• Brønsted Base Assisted Photoredox Catalysis: Proton Coupled Electron Transfer for Remote C−C Bond Formation via Amidyl Radicals
  作者：Jiaqi Jia、Yee Ann Ho、Raoul F. Bülow、Magnus Rueping

  DOI：10.1002/chem.201802907

  日期：2018.9.20

  The synthesis of alkyne‐ and alkene‐decorated lactams has been achieved through a photoredox‐initiated radical cascade reaction. The developed Brønsted base assisted, photoredox‐catalyzed, intramolecular 5‐exo‐trig cyclization/intermolecular radical addition/elimination reaction provides facile access to functionalized γ‐lactams, with good functional group tolerance and high yields.

  炔烃和烯烃修饰的内酰胺的合成是通过光氧化还原引发的自由基级联反应实现的。所开发的布朗斯台德碱的帮助下，photoredox催化分子内-5-外- TRIG环化/分子间基加/消除反应提供容易访问官能γ内酰胺类，具有良好的官能团耐受性和高的产率。
• Photoinduced remote regioselective radical alkynylation of unactivated C–H bonds
  作者：Qu-Ping Hu、Yu-Tao Liu、Yong-Ze Liu、Fei Pan

  DOI：10.1039/d1cc06885g

  日期：——

  method for the remote regioselective alkynylation of unactivated C(sp3)–H bonds in diverse aliphatic amides by photogenerated amidyl radicals has been developed. The site-selectivity is dominated via a 1,5-hydrogen atom transfer (HAT) process of the amide. Mild reaction conditions and high regioselectivity are demonstrated in this methodology.

  已经开发了一种通过光生酰胺基自由基对不同脂肪族酰胺中未活化的 C(sp 3 )-H 键进行远程区域选择性炔基化的方法。位点选择性主要通过酰胺的 1,5-氢原子转移 (HAT) 过程。该方法证明了温和的反应条件和高区域选择性。
• Direct synthesis of C3-alkynyl pyrroloindolines from tryptamines <i>via</i> a visible-light-induced radical cascade reaction
  作者：LinLin Ren、Yonggong Wang、Yanman Huo、Xiaogang Tong、Chengfeng Xia

  DOI：10.1039/d2cc05905c

  日期：——

  A visible-light-induced radical cascade reaction for the direct alkynylation of tryptamines with alkynyl sulfones was developed, affording a series of C3-alkynyl pyrroloindolines in excellent yields. This method features readily available substrates, good functional group tolerability, and scalability. C3-alkynyl pyrroloindolines show great potential as useful building blocks in the preparation of

  开发了一种可见光诱导的自由基级联反应，用于色胺与炔基砜的直接炔基化，以优异的收率提供了一系列 C3-炔基吡咯并二氢吲哚。该方法具有现成的底物、良好的官能团耐受性和可扩展性。C3-炔基吡咯并二氢吲哚在制备复杂且有价值的吡咯并二氢吲哚生物碱方面显示出作为有用结构单元的巨大潜力。