5-(thiophen-3-yl)isoquinoline | 374554-29-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 5-(thiophen-3-yl)isoquinoline
• 英文别名: 5-thiophen-3-ylisoquinoline
• CAS: 374554-29-7
• 化学式: C₁₃H₉NS
• 分子量: 211.287
• InChiKey: WXVDACXTCZQZBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(thiophen-3-yl)isoquinoline 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 5-(thiophen-3-yl)isoquinoline 2-oxide
  参考文献：
  名称：

  N-coating heterocyclic compounds

  摘要：

  公式(I)的化合物：其中A是氢原子，一个可选地取代的、不饱和的、含氮的杂环基团，或者公式(a)的基团：其中R是一个可选地取代的芳香族基团或者一个可选地取代的杂环基团；M是—(CH2)n-, —(CH2)n-O—(CH2)m-或—(CH2)n-NH—(CH2)m-，其中n和m各自为0、1或2；Q是一个可选地取代的环烷基烯基团、一个可选地取代的芳香族基团或者一个可选地取代的二价杂环基团；以及公式(b)的部分：是一个可选地取代的、不饱和的、单环、双环、三环或四环的、含氮的杂环基团，它可以包含作为环成员的额外杂原子，选自由氮、氧和硫原子组成的组，其前药或药用盐。

  公开号：

  US20030176454A1
• 作为产物：
  描述：

  3-噻吩硼酸 、 isoquinolin-5-yl methanesulfonate 在 potassium phosphate 、 NiCl₂(PCy₃)2 作用下， 反应 12.0h， 以99%的产率得到5-(thiophen-3-yl)isoquinoline
  参考文献：
  名称：

  Nickel-Catalyzed Suzuki–Miyaura Couplings in Green Solvents

  摘要：

  The nickel-catalyzed Suzuki-Miyaura coupling of aryl halides and phenol-derived substrates with aryl boronic acids using green solvents, such as 2-Me-THF and tert-amyl alcohol, is reported. This methodology employs the commercially available and air-stable precatalyst, NiCl2(PCy3)(2), and gives biaryl products in synthetically useful to excellent yields. Using this protocol, bis(heterocyclic) frameworks can be assembled efficiently.

  DOI：

  10.1021/ol401727y

文献信息

• Exploiting the umpolung reactivity of diazo groups: direct access to triazolyl-azaarenes from azaarenes
  作者：Lalita Devi、Prashant Kumar、Ruchir Kant、Namrata Rastogi

  DOI：10.1039/d2cc01897g

  日期：——

  the reaction. The methodology capitalizes on the umpolung nature of α-aryliodonio diazo compounds for installing a nucleophile, i.e. azaarene, at their α-position. Subsequent ylide formation and intramolecular 1,5-cyclization furnished 4,3-fused 1,2,4-triazolyl-azaarenes in good yields. The reaction is notable for its mild conditions, operational simplicity and fairly general scope.

  目前的工作记录了氮杂芳烃（主要是异喹啉）与高价碘重氮试剂 (HIDR) 的亲电取代，然后以串联方式进行正式的 [3+2]-偶极环加成。其他氮杂芳烃即。吡啶和菲啶也可以成功地用于该反应。该方法利用 α-aryliodonio 重氮化合物的 umpolung 特性，在其 α 位安装亲核试剂，即氮杂芳烃。随后的叶立德形成和分子内 1,5-环化以良好的收率提供了 4,3-稠合的 1,2,4-三唑基-氮杂芳烃。该反应以其温和的条件、操作简单和相当广泛的范围而著称。
• [EN] N-CONTAINING HETEROCYCLIC COMPOUNDS<br/>[FR] COMPOSES HETEROCYCLIQUES CONTENANT DE L'AZOTE
  申请人：FUJISAWA PHARMACEUTICAL CO

  公开号：WO2001087845A2

  公开（公告）日：2001-11-22

  A compound of the formula (I): wherein A is a hydrogen atom, an optionally substituted, unsaturated, N-containing heterocyclic group or a group of the formula (a) : wherein R is an optionally substituted aryl group or an optionally substituted heterocyclic group;M is -(CH2)n-, -(CH2)n-O-(CH2)m- or -(CH2)n-NH-(CH2)m-, wherein n and m are independently 0,1 or 2; Q is an optionally substituted cycloalkylene group, an optionally substituted arylene group or an optionally substituted divalent heterocyclic group; andthe moiety of the formula (b): is an optionally substituted, unsaturated, mono-, di-, tri- or tetra-cyclic, N-containing heterocyclic group which may contain additional hetero atom(s) selected from the group consisting of nitrogen, oxygen and sulfur atoms as the ring member(s), its prodrug or a pharmaceutically acceptable salt thereof.
• N-coating heterocyclic compounds
  申请人：——

  公开号：US20030176454A1

  公开（公告）日：2003-09-18

  A compound of the formula (I): wherein A is a hydrogen atom, an optionally substituted, unsaturated, N-containing heterocyclic group or a group of the formula (a): wherein R is an optionally substituted aryl group or an optionally substituted heterocyclic group; M is —(CH 2 )n-, —(CH 2 )n-O—(CH 2 )m-or —(CH 2 )n-NH—(CH 2 )m-, wherein n and m are independently 0, 1 or 2; Q is an optionally substituted cycloalkylene group, an optionally substituted arylene group or an optionally substituted divalent heterocyclic group; and the moiety of the formula (b): is an optionally substituted, unsaturated, mono-, di-, tri- or tetra-cyclic, N-containing heterocyclic group which may contain additional hetero atom(s) selected from the group consisting of nitrogen, oxygen and sulfur atoms as the ring member(s), its prodrug or a pharmaceutically acceptable salt thereof.

  公式(I)的化合物：其中A是氢原子，一个可选地取代的、不饱和的、含氮的杂环基团，或者公式(a)的基团：其中R是一个可选地取代的芳香族基团或者一个可选地取代的杂环基团；M是—(CH2)n-, —(CH2)n-O—(CH2)m-或—(CH2)n-NH—(CH2)m-，其中n和m各自为0、1或2；Q是一个可选地取代的环烷基烯基团、一个可选地取代的芳香族基团或者一个可选地取代的二价杂环基团；以及公式(b)的部分：是一个可选地取代的、不饱和的、单环、双环、三环或四环的、含氮的杂环基团，它可以包含作为环成员的额外杂原子，选自由氮、氧和硫原子组成的组，其前药或药用盐。
• Nickel-Catalyzed Suzuki–Miyaura Couplings in Green Solvents
  作者：Stephen D. Ramgren、Liana Hie、Yuxuan Ye、Neil K. Garg

  DOI：10.1021/ol401727y

  日期：2013.8.2

  The nickel-catalyzed Suzuki-Miyaura coupling of aryl halides and phenol-derived substrates with aryl boronic acids using green solvents, such as 2-Me-THF and tert-amyl alcohol, is reported. This methodology employs the commercially available and air-stable precatalyst, NiCl2(PCy3)(2), and gives biaryl products in synthetically useful to excellent yields. Using this protocol, bis(heterocyclic) frameworks can be assembled efficiently.