(2-iodophenyl)(methyl)selane | 882868-17-9

• 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-iodophenyl)(methyl)selane
• 英文别名: 2-iodophenyl methyl selenide；1-Iodo-2-methylselanylbenzene
• CAS: 882868-17-9
• 化学式: C₇H₇ISe
• 分子量: 296.997
• InChiKey: LIZHEWXSQIIVSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.67
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 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-iodophenyl)(methyl)selane 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 (2-ethynylphenyl)(methyl)selane
  参考文献：
  名称：

  Cascade Annulation of 2-Alkynylthioanisoles with Unsaturated α-Bromocarbonyls Leading to Thio-Benzobicyclic Skeletons

  摘要：

  A protocol of Cu-catalyzed annulation of phenylethynylsulfanes with unsaturated alpha-bromocarbonyls for the construction of thio-benzobicyclic skeletons is described. In this single reaction, three new bonds and two new rings can be established, highlighting the step-economics and high efficiency of this protocol.

  DOI：

  10.1021/acs.joc.8b02001
• 作为产物：
  描述：

  2-碘苯胺 在 18-冠醚-6 、 potassium acetate 、 sodium nitrite 作用下， 以 氯仿 、 水 为溶剂， 反应 15.33h， 生成 (2-iodophenyl)(methyl)selane
  参考文献：
  名称：

  2-炔基茴香硫醚与二硫化物的光诱导自由基环化，无需外部光催化剂

  摘要：

  开发了一种通过 2-炔基苯硫基苯甲醚与二硫化物光驱动自由基环化合成 3-芳基硫代苯并[ b ]噻吩的有效策略。该反应在可见光照射下顺利进行，无需任何外部光催化剂，并以高产率生成具有良好官能团耐受性的所需产物。

  DOI：

  10.1021/acs.joc.3c01776

文献信息

• Competition Studies in Alkyne Electrophilic Cyclization Reactions
  作者：Saurabh Mehta、Jesse P. Waldo、Richard C. Larock

  DOI：10.1021/jo802196r

  日期：2009.2.6

  toward alkyne electrophilic cyclization reactions has been studied. The required diarylalkynes have been prepared by consecutive Sonogashira reactions of appropriately substituted aryl halides and competitive cyclizations have been performed using I2, ICl, NBS and PhSeCl as electrophiles. The results indicate that the nucleophilicity of the competing functional groups, polarization of the alkyne triple

  已经研究了各种官能团对炔烃亲电环化反应的相对反应性。所需的二芳基炔已通过适当取代的芳基卤化物的连续 Sonogashira 反应制备，并使用 I 2、ICl、NBS 和 PhSeCl 作为亲电子试剂进行竞争性环化。结果表明，竞争官能团的亲核性、炔烃三键的极化和中间体的阳离子性质是决定这些反应结果的最重要因素。
• Synthesis of Optically Active Selenium-Containing Isotryptophan, Homoiso­tryptophan, and Homotryptophan
  作者：Koushik Goswami、Amrita Chakraborty、Surajit Sinha

  DOI：10.1002/ejoc.201300352

  日期：2013.6

  Selenoisotryptophan and its higher homologues were synthesized by Sonogashira coupling of iodophenyl methyl selenide and alkynyloxazolidines followed by iodocyclization as the key step. Sonogashira coupling of 3-iodobenzoselenophene with ethynyloxazolidine allowed the synthesis of selenohomotryptophan.

  硒异色氨酸及其高级同系物是通过碘苯基甲基硒化物和炔基恶唑烷的 Sonogashira 偶联合成，然后是碘环化作为关键步骤。3-碘苯并硒酚与乙炔恶唑烷的 Sonogashira 偶联允许合成硒高色氨酸。
• Synthesis of 2,3-Disubstituted Benzo[<i>b</i>]selenophenes via Electrophilic Cyclization
  作者：Tanay Kesharwani、Shilpa A. Worlikar、Richard C. Larock

  DOI：10.1021/jo0524268

  日期：2006.3.1

  2,3-Disubstituted benzo[b]selenophenes have been prepared by the electrophilic cyclization of various 1-(1-alkynyl)-2-(methylseleno)arenes by Br2, NBS, I2, ICl, PhSeCl, PhSeBr, and Hg(OAc)2. This method tolerates a wide variety of functional groups, including alcohol, ester, nitrile, nitro, and silyl groups, and proceeds under exceptionally mild reaction conditions.

  通过Br 2，NBS，I 2，ICl，PhSeCl，PhSeBr和Hg对各种1-（1-炔基）-2-（甲基硒代）芳烃进行亲电环化反应，制备了2,3-二取代的苯并[ b ]硒代苯（OAc）2。该方法可耐受多种官能团，包括醇，酯，腈，硝基和甲硅烷基，并在异常温和的反应条件下进行。
• Divergent Synthesis of Fused Tetracyclic Heterocycles from Diarylalkynes Enabled by the Selective Insertion of Isocyanide
  作者：Meng Li、Ruixue Zhang、Qiushan Gao、Huanfeng Jiang、Ming Lei、Wanqing Wu

  DOI：10.1002/anie.202208203

  日期：2022.10.17

  A highly selective synthesis of six different fused tetracyclic heterocycles from readily available diarylalkynes and isocyanides is disclosed. It has high step economy and good functional tolerance. An unprecedented intermolecular nucleopalladation of diarylalkynes occurs enabled by a sequential double isocyanide insertion.

  公开了从容易获得的二芳基炔烃和异氰化物高度选择性地合成六种不同的稠合四环杂环。它具有高步经济性和良好的功能耐受性。通过连续的双异氰化物插入实现了二芳基炔烃前所未有的分子间核钯化。
• Linear and Angular Heteroacenes from Double-Electrophilic Cyclization (DEC) and DEC-Reductive Elimination of Diynes
  作者：Akhil Gupta、Bernard L. Flynn

  DOI：10.1021/acs.orglett.7b00265

  日期：2017.4.21

  Linear and angular heteroacenes are prepared from terminal alkynes bearing tethered nucleophiles in two steps. Linear heteroacenes are formed from the homocoupling of these alkynes followed by reaction with a double electrophile (ECl2) to induce a tricyclization reaction cascade involving double-electrophilic cyclization (DEC). Related angular heteroacenes are formed from the prior substitution of the chloro groups in ECl2 with the same terminal alkyne followed by reaction with AuCl3 to produce a DEC-reductive-elimination (DECRE) reaction.