1,4-bis(2-(methylthio)phenyl)buta-1,3-diyne | 1208500-39-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1,4-bis(2-(methylthio)phenyl)buta-1,3-diyne
• 英文别名: 1-Methylsulfanyl-2-[4-(2-methylsulfanylphenyl)buta-1,3-diynyl]benzene；1-methylsulfanyl-2-[4-(2-methylsulfanylphenyl)buta-1,3-diynyl]benzene
• CAS: 1208500-39-3
• 化学式: C₁₈H₁₄S₂
• 分子量: 294.441
• InChiKey: AHNJOWBLOBSZLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,4-bis(2-(methylthio)phenyl)buta-1,3-diyne 在 碘 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以98%的产率得到3,3'-diiodo-2,2'-bibenzo[b]thiophene
  参考文献：
  名称：

  碘/钯合成多杂环化合物的方法

  摘要：

  报道了一种简单、直接的合成多杂环化合物 (PHC) 的策略，该策略涉及钯催化的 Sonogashira 偶联的迭代循环，然后使用 I 2或 ICl进行碘环化。多种杂环单元，包括苯并呋喃、苯并噻吩、吲哚和异香豆素，可以在温和的反应条件下有效地结合。此外，这种策略的变体提供了各种连接和融合的 PHC。

  DOI：

  10.1021/jo902639f
• 作为产物：
  描述：

  1-乙炔基-2-(甲硫基)苯 在 吡啶 、 copper(II) acetate monohydrate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以61.6%的产率得到1,4-bis(2-(methylthio)phenyl)buta-1,3-diyne
  参考文献：
  名称：

  Linear and Angular Heteroacenes from Double-Electrophilic Cyclization (DEC) and DEC-Reductive Elimination of Diynes

  摘要：

  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.

  DOI：

  10.1021/acs.orglett.7b00265

文献信息

• MPHT-Promoted Bromocyclization of ortho-Substituted Arylalkynes: Application to the Synthesis of 2-Substituted 3-Bromobenzofurans and -Benzo[b]thiophenes
  作者：Maud Jacubert、Abdellatif Tikad、Olivier Provot、Abdallah Hamze、Jean-Daniel Brion、Mouâd Alami

  DOI：10.1002/ejoc.201000529

  日期：——

  A convenient and general approach to the synthesis of 2‐substituted 3‐bromobenzofurans and ‐benzothiophenes was developed. The procedure is based on the cyclization of ortho‐substituted arylalkynes in the presence of N‐methylpyrrolidin‐2‐one hydrotribromide (MPHT) as a soft and easy‐to‐handle electrophilic brominating reagent. Under mild reaction conditions, MPHT promoted the bromocyclization of various

  开发了一种合成 2-取代 3-溴苯并呋喃和-苯并噻吩的简便通用方法。该过程基于邻位取代芳炔在 N-甲基吡咯烷-2-酮氢三溴化物 (MPHT) 作为柔软且易于处理的亲电子溴化试剂存在下的环化反应。在温和的反应条件下，MPHT 促进了各种烯炔和二炔以及芳炔的溴环化，以高产率获得 2-取代的 3-溴苯并呋喃和-苯并噻吩。随后在 C-Br 键上通过钯催化的偶联反应进行的功能化提供了获得具有生物学意义的 2,3-二取代苯并呋喃和苯并噻吩的通用途径。
• Iodine/Palladium Approaches to the Synthesis of Polyheterocyclic Compounds
  作者：Saurabh Mehta、Richard C. Larock

  DOI：10.1021/jo902639f

  日期：2010.3.5

  A simple, straightforward strategy for the synthesis of polyheterocyclic compounds (PHCs) is reported, which involves iterative cycles of palladium-catalyzed Sonogashira coupling, followed by iodocyclization using I2 or ICl. A variety of heterocyclic units, including benzofurans, benzothiophenes, indoles, and isocoumarins, can be efficiently incorporated under mild reaction conditions. In addition

  报道了一种简单、直接的合成多杂环化合物 (PHC) 的策略，该策略涉及钯催化的 Sonogashira 偶联的迭代循环，然后使用 I 2或 ICl进行碘环化。多种杂环单元，包括苯并呋喃、苯并噻吩、吲哚和异香豆素，可以在温和的反应条件下有效地结合。此外，这种策略的变体提供了各种连接和融合的 PHC。
• Cascade Annulation of 2-Alkynylthioanisoles with Unsaturated α-Bromocarbonyls Leading to Thio-Benzobicyclic Skeletons
  作者：Yuzhen Gao、Pengbo Zhang、Gang Li、Yufen Zhao

  DOI：10.1021/acs.joc.8b02001

  日期：2018.11.16

  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.
• 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.