4-(2-丙炔氧基)喹唑啉 | 108160-14-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 4-(2-丙炔氧基)喹唑啉
• 中文别名: 4-(丙-2-炔-1-基氧基)喹唑啉
• 英文名称: 4-(2-propynyloxy)quinazoline
• 英文别名: 4-propargyloxyquinazoline；4-(Prop-2-yn-1-yloxy)quinazoline；4-prop-2-ynoxyquinazoline
• CAS: 108160-14-1
• 化学式: C₁₁H₈N₂O
• mdl: MFCD27941374
• 分子量: 184.197
• InChiKey: ABHBKLQMVZBGDR-UHFFFAOYSA-N

物化性质

• 熔点：
  127 °C
• 沸点：
  338.0±22.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  35
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2-丙炔氧基)喹唑啉 以 邻二氯苯 为溶剂， 反应 12.0h， 以13%的产率得到3,3'-((1Z,1'E)-cyclobutane-1,2-diylidenebis(methanylylidene))bis(quinazolin-4(3H)-one)
  参考文献：
  名称：

  嘌呤的正常o→N克莱森重排的证明

  摘要：

  6-烯丙氧基-9-苄基嘌呤（2）和9-苄基-6-炔丙氧基嘌呤（5）在纯净或在邻二氯苯中进行正常的O→N [3,3]热重排。后者导致了新的1-烯基-9-苄基次黄嘌呤（6）。相关的4-烯丙氧基和4-炔丙氧基喹唑啉；（9，12）也经历了顺畅的O→N Claisen热重排。在（12）的情况下，初级艾伦产物进一步转化为3-炔丙基喹唑啉-4-酮（13）和丙二烯二聚体（14）。

  DOI：

  10.1016/s0040-4020(01)82069-x
• 作为产物：
  描述：

  4-羟基喹唑啉 、 2-丙炔-1-醇 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 caesium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 4.83h， 以75%的产率得到4-(2-丙炔氧基)喹唑啉
  参考文献：
  名称：

  One-Pot Etherification of Purine Nucleosides and Pyrimidines

  摘要：

  A one-pot synthesis of ethers derived from inosine, guanosine, 2'-deoxyguanosine, and pyrimidinones is described Exposure of the heterocycle to 1H-benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (BOP) and Cs2CO3 produces a reactive intermediate, which is converted to the desired ether by subsequent addition of an appropriate alcohol or phenol and Cs2CO3. Although rapid formation of HMPA from BOP can occur in the presence of an alcohol and base, as demonstrated by the reaction with methanol, under appropriate conditions these heteroaryl ethers can be efficiently synthesized

  DOI：

  10.1021/ol101655h

文献信息

• Synthesis of medicinally important quinazolines decorated with 1,4-disubstituted-1,2,3-triazoles using CuSO₄·5H₂O–Et₃N catalytic system
  作者：Monika Vashist、Khushbu Kushwaha、Reena Kaushik、Subhash C. Jain

  DOI：10.1039/c4ra02123a

  日期：——

  The direct use of Cu(ii) sulfate pentahydrate in the presence of triethylamine afforded 1,4-disubstituted-1,2,3-triazoles via 1,3-dipolar cycloaddition of terminal alkyne(s) to azide(s) at room temperature.

  在三乙胺存在下，直接使用硫酸铜(II)五水合物，在室温下通过末端炔烃与偶氮化物的1,3-偶极环加成反应，得到1,4-二取代-1,2,3-三唑。
• RANGANATHAN DARSHAN; RAMESH RATHI; KESAVAN KRISHNAN; SINGH WAHEGURU PAL, TETRAHEDRON, 42,(1986) N 17, 4873-4878
  作者：RANGANATHAN DARSHAN、 RAMESH RATHI、 KESAVAN KRISHNAN、 SINGH WAHEGURU PAL

  DOI：——

  日期：——
• One-Pot Etherification of Purine Nucleosides and Pyrimidines
  作者：Hari Prasad Kokatla、Mahesh K. Lakshman

  DOI：10.1021/ol101655h

  日期：2010.10.15

  A one-pot synthesis of ethers derived from inosine, guanosine, 2'-deoxyguanosine, and pyrimidinones is described Exposure of the heterocycle to 1H-benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (BOP) and Cs2CO3 produces a reactive intermediate, which is converted to the desired ether by subsequent addition of an appropriate alcohol or phenol and Cs2CO3. Although rapid formation of HMPA from BOP can occur in the presence of an alcohol and base, as demonstrated by the reaction with methanol, under appropriate conditions these heteroaryl ethers can be efficiently synthesized
• The demonstration of normal o →N claisen rearrangement in purines
  作者：Darshan Ranganathan、Ramesh Rathi、Krishnan Keshavan、Waheguru Pal Singh

  DOI：10.1016/s0040-4020(01)82069-x

  日期：1986.1

  6-Allyloxy-9-benzylpurine (2) and 9-benzyl-6-propargyloxy purine (5) undergo normal thermal O→N [3,3] rearrangement, either neat or in o-dichlorobenzene. The latter leads to the novel, 1-allenyl-9-benzyl-hypoxanthine (6). The related 4-allyloxy and 4-propargyloxy quinazoline; (9, 12) also undergo smooth thermal O→N Claisen rearrangement. In the case of(12), the primary allenic product is further transformed into

  6-烯丙氧基-9-苄基嘌呤（2）和9-苄基-6-炔丙氧基嘌呤（5）在纯净或在邻二氯苯中进行正常的O→N [3,3]热重排。后者导致了新的1-烯基-9-苄基次黄嘌呤（6）。相关的4-烯丙氧基和4-炔丙氧基喹唑啉；（9，12）也经历了顺畅的O→N Claisen热重排。在（12）的情况下，初级艾伦产物进一步转化为3-炔丙基喹唑啉-4-酮（13）和丙二烯二聚体（14）。