(Z)-2-(2-iodovinyl)naphthalene | 168007-02-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (Z)-2-(2-iodovinyl)naphthalene
• 英文别名: 2-[(Z)-2-iodoethenyl]naphthalene
• CAS: 168007-02-1
• 化学式: C₁₂H₉I
• 分子量: 280.108
• InChiKey: JMUKXKKYWOLRJF-FPLPWBNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 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：

  (Z)-2-(2-iodovinyl)naphthalene 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以92%的产率得到2-乙基萘
  参考文献：
  名称：

  Terminal alkynes from aldehydes via dehydrohalogenation of (Z)-1-iodo-1-alkenes with TBAF

  摘要：

  Terminal alkynes were prepared in near quantitative yields via dehydrohalogenation of (Z)-1-iodo-1-alkenes with tetrabutylammonium fluoride (TBAF) under mild conditions. The methodology was expanded to include a one-pot, direct synthesis of terminal alkynes from aldehydes Without the necessity of isolating and purifying the intermediate iodoalkene. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.09.060
• 作为产物：
  描述：

  (Z)-1-(2-naphthyl)-2-trimethylsilylethene 在 N-碘代丁二酰亚胺 作用下， 以 乙腈 为溶剂， 以86%的产率得到(Z)-2-(2-iodovinyl)naphthalene
  参考文献：
  名称：

  Synthesis of the racemic forms of carbon–carbon double bond locked analogues of strobilurins which are characterized by a 2-arylcyclopropane ring cis-substituted at C-1 by the methyl (E)-3-methoxypropenoate unit

  摘要：

  The racemic forms of three new carbon-carbon double bond locked analogues of strobilurins, which are characterized by a 2-arylcyclopropane ring cis-substituted at C-1 by the methyl (E)-3-methoxypropenoate unit, have been synthesized according to a strategy which involves the palladiuin-catalyzed synthesis of methyl (E)-3-methoxy-2-[(Z)-2-(aryl)ethenyl]propenoates and their stereospecific cyclopropanation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00334-4

文献信息

• Cyclic Vinyl(aryl)iodonium Salts: Synthesis and Reactivity
  作者：Konrad Kepski、Craig R. Rice、Wesley J. Moran

  DOI：10.1021/acs.orglett.9b02540

  日期：2019.9.6

  A convenient, highly regioselective synthesis of five-membered cyclic vinyl(aryl)iodonium salts directly from β-iodostyrenes is presented. An X-ray crystal structure confirms the identity of these heterocycles. These λ3-iodanes can be converted rapidly into functionalized arylacetylenes by treatment with mild base or undergo SNV reactions with nonbasic nucleophiles.

  提出了一种直接从β-碘苯乙烯中方便地，高度区域选择性地合成五元环乙烯基（芳基）碘鎓盐的方法。X射线晶体结构证实了这些杂环的身份。通过用温和的碱处理，这些λ3-碘化物可以迅速转化为官能化的芳基乙炔，或与非碱性亲核试剂进行SNV反应。
• Chromium-catalyzed olefination of arylaldehydes with haloforms assisted by 2,3,5,6-tetramethyl-<i>N</i>,<i>N</i>′-bis(trimethylsilyl)-1,4-dihydropyrazine
  作者：Kohei Nishi、Hayato Tsurugi、Kazushi Mashima

  DOI：10.1039/d2cc06104j

  日期：——

  Chromium-catalyzed olefination of arylaldehydes with haloforms was achieved using 2,3,5,6-tetramethyl-N,N′-bis(trimethylsilyl)-1,4-dihydropyrazine (1a) as an organic reducing agent, giving β-halostyrene derivatives in a trans-selective manner. The reaction required no metal powders, such as zinc and manganese, as reductants, thereby minimizing metal-based reaction waste.

  以2,3,5,6-四甲基-N , N'-双(三甲基甲硅烷基)-1,4-二氢吡嗪( 1a )为有机还原剂,铬催化卤代芳醛烯化,得到β-卤代苯乙烯衍生物以反式选择的方式。该反应不需要锌和锰等金属粉末作为还原剂，从而最大限度地减少了金属基反应废物。
• Synthesis of <i>N</i>‐Acylsulfenamides from (Hetero)Aryl Iodides and Boronic Acids by One‐Pot Sulfur‐Arylation and Dealkylation
  作者：Nathaniel S. Greenwood、Nicholas P. Cerny、Anthony P. Deziel、Jonathan A. Ellman

  DOI：10.1002/anie.202315701

  日期：2024.1.15

  general one-pot approach for the synthesis of N-acylsulfenamides from commercially abundant (hetero)aryl iodides and boronic acids is reported. Broad scope and high functional group compatibility were observed including for late-stage incorporation of sulfenamide functionality in complex drugs and drug precursors. Sulfur-functionalization then enables the synthesis of diverse, medicinally relevant

  报道了一种从商业丰富的（杂）芳基碘化物和硼酸合成 N-酰基次磺酰胺的通用一锅法。观察到广泛的范围和高官能团相容性，包括在复杂药物和药物前体中掺入次磺酰胺官能团的后期。然后，硫官能化能够合成多种多样的、医学相关的高氧化态硫药效团。
• Design, synthesis and anti-inflammatory activity study of lansiumamide analogues for treatment of acute lung injury
  作者：Liyan Song、Gang Li、Wen Guan、Zhijun Zeng、Yanghui Ou、Tongchao Zhao、Jiayu Li、Dengqin He、Xiangxiang Fang、Yali Zhang、Jia-qiang Wu、Rongbiao Tong、Hongliang Yao

  DOI：10.1016/j.biopha.2023.115412

  日期：2023.10

  Acute lung injury (ALI) is an inflammation-mediated respiratory disease with a high mortality rate. Medications with anti-inflammatory small molecules have been demonstrated in phase I and II clinical trials to considerably reduce the ALI mortality. In this study, two series of lansiumamide analogues were designed, synthesized, and evaluated for anti-inflammatory activity for ALI treatment. We found

  急性肺损伤（ALI）是一种炎症介导的呼吸道疾病，死亡率很高。I 期和 II 期临床试验已证明含有抗炎小分子的药物可显着降低 ALI 死亡率。在这项研究中，设计、合成了两个系列的兰硫酰胺类似物，并评估了其治疗 ALI 的抗炎活性。我们发现化合物8n通过抑制LPS诱导的Raw264.7细胞中促炎细胞因子白细胞介素6（IL-6）和白细胞介素1β（IL-1β）的表达并激活Nrf2/HO表现出最佳的抗炎活性。 -1途径。此外，我们在LPS诱导的ALI小鼠模型中发现，化合物8n显着减少炎症细胞向肺组织的浸润，从而达到保护肺组织和改善ALI的效果。此外，我们的小鼠模型研究表明，化合物8n具有良好的祛痰作用。这些结果一致支持兰硫酰胺类似物8n代表了一类新型抗炎药，有潜力作为先导化合物进一步开发为治疗 ALI 的治疗药物。
• IPy2BF4 is also a useful reagent for stereospecific iodine-silicon exchange in open chain trimethylsilylalkenes
  作者：José Barluenga、Lorenzo J. Alvarez-García、JoséM. González

  DOI：10.1016/0040-4039(95)00199-m

  日期：1995.3

  Reaction of the title monosubstituted vinylsilanes with IPy(2)BF(4)/HBF4 gives iodoalkenes through the ipso-substitution process with stereospecific retention of configuration.