2-formyl-4-ethynyl-3,5-dimethylpyrrole | 65613-21-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-formyl-4-ethynyl-3,5-dimethylpyrrole
• 英文别名: 4-ethynyl-3,5-dimethyl-pyrrole-2-carbaldehyde；2-Formyl-4-ethynyl-3,5-dimethyl-pyrrole；4-ethynyl-3,5-dimethyl-1H-pyrrole-2-carbaldehyde
• CAS: 65613-21-0
• 化学式: C₉H₉NO
• 分子量: 147.177
• InChiKey: KPNRNRJGQXHAGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-formyl-4-ethynyl-3,5-dimethylpyrrole 在 氢溴酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 1.0h， 生成 3-ethyl-5-((4-ethynyl-3,5-dimethyl-2H-pyrrol-2-ylidene)methyl)-2,4-dimethyl-1H-pyrrole
  参考文献：
  名称：

  不对称联吡啶和F -BODIPY与末端炔烃和烯烃共轭

  摘要：

  具有共轭末端炔取代基的不对称中氢二吡啶被转化为其相应的二氟硼配合物，并使用Sonogashira交叉偶联扩展了π共轭的程度。用BF 3 ·OEt 2和NEt 3处理炔烃取代的双吡啶具有共轭末端炔烃对路易斯活化的亲电取代基的反应性，并导致带有末端溴乙烯和烯醇取代基的F -BODIPY的分离。

  DOI：

  10.1021/acs.joc.7b01129
• 作为产物：
  描述：

  3,5-二甲基-2-吡咯甲醛 在 copper(l) iodide 、 dichlorobis(triphenylphosphine)palladium(II) 、 四丁基氟化铵 、 碘 、 二乙胺 、 potassium iodide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 生成 2-formyl-4-ethynyl-3,5-dimethylpyrrole
  参考文献：
  名称：

  Synthesis and spectral properties of new 3,3’-bis(dipyrrolylmethene) with acetylene spacer

  摘要：

  Bis(2,4,7,9-tetramethyl-8-ethyldipyrrolylmethen-3-yl)acetylene dihydrobromide (H2L center dot 2HBr), new bis(dipyrrolylmethene), in whose molecule dipyrrolylmethene domains were connected through 3,3'-carbon atoms of internal pyrrole nuclei by acetylene spacer, were synthesized by original procedure. The compound was characterized by element analysis, IR, H-1 NMR, and electronic spectroscopy. The comparative analysis of spectral properties shows the reduction of the basicity of H2L ligand in comparison with the structural analogs, which contain internal methylene spacer. The quantum-chemical simulation showed that the rigid acetylene spacer gives linear structure to the H2L molecule in contrast to the spiral-shaped geometry of structural analogs with -CH2- spacer.

  DOI：

  10.1134/s107036321011023x

文献信息

• MIRONOW A. F.; KOZHICH D. T.; VASILEVSKY V. I.; EVSTIGNEEVA R. P., SYNTHESIS, 1979, NO 7, 533-535
  作者：MIRONOW A. F.、 KOZHICH D. T.、 VASILEVSKY V. I.、 EVSTIGNEEVA R. P.

  DOI：——

  日期：——
• KOZHICH D. T.; AKIMENKO L. V.; MIRONOV A. F.; EVSTIGNEEVA R. P., ZH. ORGAN. XIMII, 1977, 13, HO 12, 2604-2608
  作者：KOZHICH D. T.、 AKIMENKO L. V.、 MIRONOV A. F.、 EVSTIGNEEVA R. P.

  DOI：——

  日期：——
• [EN] OXINDOLE COMPOUNDS FOR USE AS MAP4K1 INHIBITORS<br/>[FR] COMPOSÉS D'OXINDOLE DESTINÉS À ÊTRE UTILISÉS EN TANT QU'INHIBITEURS DE MAP4K1
  申请人：ICHNOS SCIENCES S A

  公开号：WO2020070332A1

  公开（公告）日：2020-04-09

  The invention relates to novel inhibitors of MAP4K1 (HPK1), useful for the treatment of diseases or disorders characterized by characterized dysregulation of the signal transduction pathways associated with MAPK activation, including hyperproliferative diseases, diseases of immune system dysfunction, inflammatory disorders, neurological diseases, and cardiovascular diseases. The invention further relates to pharmaceutical compositions comprising the same and methods of treatment of said diseases and disorders. (Formula I)
• Synthesis and spectral properties of new 3,3’-bis(dipyrrolylmethene) with acetylene spacer
  作者：E. V. Antina、G. B. Guseva、A. E. Loginova、A. S. Semeikin、A. I. V’yugin

  DOI：10.1134/s107036321011023x

  日期：2010.11

  Bis(2,4,7,9-tetramethyl-8-ethyldipyrrolylmethen-3-yl)acetylene dihydrobromide (H2L center dot 2HBr), new bis(dipyrrolylmethene), in whose molecule dipyrrolylmethene domains were connected through 3,3'-carbon atoms of internal pyrrole nuclei by acetylene spacer, were synthesized by original procedure. The compound was characterized by element analysis, IR, H-1 NMR, and electronic spectroscopy. The comparative analysis of spectral properties shows the reduction of the basicity of H2L ligand in comparison with the structural analogs, which contain internal methylene spacer. The quantum-chemical simulation showed that the rigid acetylene spacer gives linear structure to the H2L molecule in contrast to the spiral-shaped geometry of structural analogs with -CH2- spacer.
• Asymmetric Dipyrrin and <i>F</i>-BODIPYs Conjugated to Terminal Alkynes and Alkenes
  作者：Carlotta Figliola、Katherine N. Robertson、Sarah Greening、Alison Thompson

  DOI：10.1021/acs.joc.7b01129

  日期：2017.7.7

  meso-H dipyrrin featuring a conjugated terminal alkyne substituent was converted to its corresponding difluoro boron complex, and the extent of π-conjugation was extended using Sonogashira cross-coupling. Treatment of the alkyne-substituted dipyrrin with BF3·OEt2 and NEt3 revealed the reactivity of the conjugated terminal alkyne toward Lewis-activated electrophilic substitution and led to the isolation

  具有共轭末端炔取代基的不对称中氢二吡啶被转化为其相应的二氟硼配合物，并使用Sonogashira交叉偶联扩展了π共轭的程度。用BF 3 ·OEt 2和NEt 3处理炔烃取代的双吡啶具有共轭末端炔烃对路易斯活化的亲电取代基的反应性，并导致带有末端溴乙烯和烯醇取代基的F -BODIPY的分离。