1-cyanopyrazolo[5,1-a]isoquinoline | 25627-90-1

• 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: 1-cyanopyrazolo[5,1-a]isoquinoline
• 英文别名: pyrazolo[5,1-a]isoquinoline-1-carbonitrile；1-Cyanpyrazolo<5,1-a>isochinolin；Pyrazolo[5,1-a]isoquinoline-1-carbonitrile
• CAS: 25627-90-1
• 化学式: C₁₂H₇N₃
• 分子量: 193.208
• InChiKey: RVRSWLOVVZYVHU-UHFFFAOYSA-N

物化性质

• 熔点：
  147 °C(Solv: ethanol (64-17-5))
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  0
• 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

• 作为产物：
  描述：

  2-amino-1-ethoxycarbonyl isoquinolinium mesitylensulfonate 、 丙烯腈 在 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以23%的产率得到1-cyanopyrazolo[5,1-a]isoquinoline
  参考文献：
  名称：

  2-Alkoxycarbonylpyridinium N-Aminides:  1,3-Dipoles or 1,4-Nucleophile−Electrophile Synthons? Experimental and Theoretical Evidence for the Mechanism of Pyrido[1,2-b]pyridazinium Inner Salt Formation

  摘要：

  2-Alkoxycarbonylpyridinium N-aminides behave as 1,3-dipoles toward acetylenic compounds and as 1,4-nucleophile-electrophiles with heterocumulenes in a [4 + 2] cyclocondensation process, yielding in the latter case conjugated mesomeric betaines. These N-aminides also behave as 1,3-dipoles when reacted with olefinic dipolarophiles, producing the corresponding cycloadducts that, depending on their regioisomeric nature, subsequently undergo a ring expansion process to produce pyrido[1,2-b]-pyridazinium inner salts. A mechanistic investigation performed using both PM3 frontier molecular orbital (FMO) and potential energy surface (PES) analysis at the RHF/6-31+G* level indicates that both the cycloaddition reaction and the ring expansion occur in a concerted way rather than through a stepwise mechanism via a zwitterionic intermediate.

  DOI：

  10.1021/jo9909655

文献信息

• PhI(OAc)2-Promoted Regioselective Cycloaddition of N-Aminopyridinium Ylides with Electron-Deficient Alkenes
  作者：Junlei Wang、Guiling Chen、Chengcheng Shi、Hongqing Li、Binbin Huang、Qinglin Xie、Guocheng Gao、Yanan Li、Haijun Du、Xiaohua Cai

  DOI：10.1055/a-2216-4594

  日期：——

  Herein, we report a regioselective cycloaddition strategy of N-aminopyridinium ylides with electron-deficient alkenes, in the presence of a hypervalent iodine reagent, PhI(OAc)2. A variety of multifunctionalized pyrazolo[1,5-a]pyridine architectures were smoothly afforded by the reactions of pyridine-, quinoline-, and isoquinoline-based N-ylides with diverse alkenes with or without a halogen atom adjacent

  在此，我们报告了在高价碘试剂 PhI(OAc) 2存在下，N -氨基吡啶鎓叶立德与缺电子烯烃的区域选择性环加成策略。通过吡啶基、喹啉基和异喹啉基N-叶立德与具有或不具有与吸电子基团相邻的卤素原子的多种烯烃的反应，顺利地得到了各种多功能化的吡唑并[1,5- a ]吡啶结构（EWG）在宽松的条件下。
• Tominaga, Yoshinori; Ichihara, Yuichi; Mori, Tomoko, Journal of Heterocyclic Chemistry, 1990, vol. 27, # 2, p. 263 - 268
  作者：Tominaga, Yoshinori、Ichihara, Yuichi、Mori, Tomoko、Kamio, Chizuko、Hosomi, Akira

  DOI：——

  日期：——
• TOMINAGA, YOSHINORI;ICHIHARA, YUICHI;MORI, TOMOKO;KAMIO, CHIZUKO;HOSOMI, +, J. HETEROCYCL. CHEM., 27,(1990) N, C. 263-268
  作者：TOMINAGA, YOSHINORI、ICHIHARA, YUICHI、MORI, TOMOKO、KAMIO, CHIZUKO、HOSOMI, +

  DOI：——

  日期：——
• 2-Alkoxycarbonylpyridinium N-Aminides:  1,3-Dipoles or 1,4-Nucleophile−Electrophile Synthons? Experimental and Theoretical Evidence for the Mechanism of Pyrido[1,2-<i>b</i>]pyridazinium Inner Salt Formation
  作者：Jesús Valenciano、Ana M. Cuadro、Juan J. Vaquero、Julio Alvarez-Builla、Raul Palmeiro、Obis Castaño

  DOI：10.1021/jo9909655

  日期：1999.12.1

  2-Alkoxycarbonylpyridinium N-aminides behave as 1,3-dipoles toward acetylenic compounds and as 1,4-nucleophile-electrophiles with heterocumulenes in a [4 + 2] cyclocondensation process, yielding in the latter case conjugated mesomeric betaines. These N-aminides also behave as 1,3-dipoles when reacted with olefinic dipolarophiles, producing the corresponding cycloadducts that, depending on their regioisomeric nature, subsequently undergo a ring expansion process to produce pyrido[1,2-b]-pyridazinium inner salts. A mechanistic investigation performed using both PM3 frontier molecular orbital (FMO) and potential energy surface (PES) analysis at the RHF/6-31+G* level indicates that both the cycloaddition reaction and the ring expansion occur in a concerted way rather than through a stepwise mechanism via a zwitterionic intermediate.