2-(1-adamantyl)indazole | 103408-90-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 英文名称: 2-(1-adamantyl)indazole
• CAS: 103408-90-8
• 化学式: C₁₇H₂₀N₂
• 分子量: 252.359
• InChiKey: AYNHCHLYVFFGKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(1-adamantyl)indazole 500.0 ℃ 、4.0 Pa 条件下， 生成 1-(1-金刚烷基)吲唑
  参考文献：
  名称：

  Perez, J. D.; Yranzo, G. I.; Ferraris, M. A., Bulletin de la Societe Chimique de France, 1991, # 4, p. 592 - 595

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(1-金刚烷基)吲唑 600.0 ℃ 、5.33 Pa 条件下， 生成 2-(1-adamantyl)indazole
  参考文献：
  名称：

  Perez, J. D.; Yranzo, G. I.; Ferraris, M. A., Bulletin de la Societe Chimique de France, 1991, # 4, p. 592 - 595

  摘要：

  DOI：

文献信息

• Cu^II–hydrotalcite catalyzed one-pot three component synthesis of 2H-indazoles by consecutive condensation, C–N and N–N bond formations
  作者：Avvari N. Prasad、Rapelli Srinivas、Benjaram M. Reddy

  DOI：10.1039/c2cy20590d

  日期：——

  An efficient and straightforward synthesis of 2H-indazoles is achieved from 2-bromobenzaldehydes, primary amines and sodium azide through consecutive condensation, C–N and N–N bond formations, catalyzed by a novel heterogeneous CuII–HT catalyst. The recoverable heterogeneous CuII–HT catalyst exhibited an impressive activity for the title reaction without any additives (expensive ligands, etc.). Heterocyclization proceeds through C–N and N–N bond formation, which is the key step to deliver the desired 2H-indazole scaffold. A series of structurally diverse 2H-indazoles were prepared in good to excellent yields from easily accessible starting materials by employing this protocol.

  一种高效且简便的2H-吲唑合成方法通过2-溴苯甲醛、初级胺和叠氮化钠，在新型的异相CuII–HT催化剂的催化下，通过连续的缩合、C–N和N–N键的形成实现。可回收的异相CuII–HT催化剂在无需任何添加剂（如昂贵的配体等）的情况下，对该反应表现出令人印象深刻的活性。杂环化反应通过C–N和N–N键的形成进行，这是获得所需2H-吲唑骨架的关键步骤。通过采用该方法，从易得的起始材料中合成了一系列结构多样的2H-吲唑，得率良好到优异。
• Consecutive Condensation, C–N and N–N Bond Formations: A Copper- Catalyzed One-Pot Three-Component Synthesis of 2<i>H</i>-Indazole
  作者：Manian Rajesh Kumar、Ahbyeol Park、Namjin Park、Sunwoo Lee

  DOI：10.1021/ol201409j

  日期：2011.7.1

  2H-Indazoles are synthesized using copper-catalyzed, one-pot, three-component reactions of 2-bromobenzaldehydes, primary amines, and sodium azide. A copper catalyst plays the key role in the formation of C-N and N-N bonds. This method has a broad substrate scope with a high tolerance for a variety of functional groups.
• Gonzalez; Alarcon; Cabildo, European Journal of Medicinal Chemistry, 1985, vol. 20, # 4, p. 359 - 362
  作者：Gonzalez、Alarcon、Cabildo、et al.

  DOI：——

  日期：——
• ——
  作者：V. G. Tsypin、V. V. Kachala、B. I. Ugrak、E. L. Golod

  DOI：10.1023/a:1015310926725

  日期：——

  Adamantylation of indazole and its C-nitro derivatives with 1-hydroxyadamantane in mineral acids yields exclusively the corresponding 1-(1-adamantyl)indazoles via attack by 1-adamantyl cation on the protonated substrate. The oxidative alkylation with 1-iodoadamantane leads to formation of 1- and 2-(1-adamantyl)indazoles, the 2-isomer prevailing.
• GONZALEZ, M. E.;ALARCON, B.;CABILDO, P.;CLARAMUNT, R. M.;SANZ, D.;ELGUERO+, EUR. J. MED. CHEM., 1985, 20, N 4, 359-362
  作者：GONZALEZ, M. E.、ALARCON, B.、CABILDO, P.、CLARAMUNT, R. M.、SANZ, D.、ELGUERO+

  DOI：——

  日期：——