(3bS,4aR)3,4,4-trimethyl-1-(4-methylquinoline-2-yl)-3b,4,4a,5-tetrahydro-1H-cyclopropane[3,4]cyclopenta[1,2-c]pyrazole | 200882-21-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (3bS,4aR)3,4,4-trimethyl-1-(4-methylquinoline-2-yl)-3b,4,4a,5-tetrahydro-1H-cyclopropane[3,4]cyclopenta[1,2-c]pyrazole
• 英文别名: (3bS,4aR)-3,4,4-trimethyl-1-(4-methylquinolin-2-yl)-3b,4,4a,5-tetrahydro-1H-cyclopropa[3,4]cyclopenta[1,2-c]pyrazole；(3bR,4aR)-3,4,4-trimethyl-1-(4-methyl-2-quinolin-2-yl)-3b,4,4a,5-tetrahydrocyclopropa[3,4]cyclopenta[1,2-c]pyrazole；(3bR,4aR)-3,4,4-trimethyl-1-(4-methylquinolin-2-yl)-3b,4,4a,5-tetrahydro-1H-cyclopropa[3,4]cyclopenta[1,2-c]pyrazole；(3bS, 4aR)-3,4,4-trimethyl-1-(4-methylquinoline-2-yl)-3b,4,4a,5-tetrahydro-1H-cyclopropa[3,4]cyclopenta[1,2-c]pyrazole；(2S,4R)-3,3,9-trimethyl-7-(4-methylquinolin-2-yl)-7,8-diazatricyclo[4.3.0.02,4]nona-1(6),8-diene
• CAS: 200882-21-9
• 化学式: C₂₀H₂₁N₃
• 分子量: 303.407
• InChiKey: HRJHJSVXCGLCEV-AUUYWEPGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  copper(II) nitrate trihydrate 、 (3bS,4aR)3,4,4-trimethyl-1-(4-methylquinoline-2-yl)-3b,4,4a,5-tetrahydro-1H-cyclopropane[3,4]cyclopenta[1,2-c]pyrazole 以 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 以50%的产率得到[cobalt(II)((3bS,4aR)3,4,4-trimethyl-1-(4-methylquinoline-2-yl)-3b,4,4a,5-tetrahydro-1H-cyclopropane[3,4]cyclopenta[1,2-c]pyrazole)(nitrate)(chloride)]
  参考文献：
  名称：

  Cobalt(II) and copper(II) complexes with chiral pyrazolylquinoline, a derivative of terpenoid (+)-3-carene. Catalytic activity in ethylene polymerization reaction

  摘要：

  Coordination compounds [CoLCl2] (I), [CuLCl(NO3)] (II), CuL(NO3)(2) (III), and CuLCl2 (IV) (where L is a chiral pyrazolylquinoline - a derivative of terpenoid (+)-3-carene) were synthesized. X-ray diffraction data showed that crystal structures I and 11 are built of mononuclear acentric molecules. In the molecule of complex 1, the Co2+ ion coordinates two N atoms of bidentate cycle-forming ligand L and two Cl atoms. The coordination polyhedron of Cl2N2 is a distorted tetrahedron. For complex I, mu(eff) = 4.50 mu(B), which corresponds to a high-spin configuration d(7). In the molecules of II(1), II(2) (which are diastereoisomers of complex II), each Cu2+ ion coordinates two N atoms of bidentate cycle-forming ligand L, the Cl atom, and two O atoms of bidenlate cyclic NO3- ion. The ClN2O2 coordination polyhedra are tetragonal pyramids with different degrees of distortion . The structure of complex II consists of supramolecular clusters, i.e., isolated chains incorporating the molecules of II(1) and II(2). The values of mu(eff) for II-IV correspond to the d(9) configuration. The results of EPR and IR study suggest that complex III contains the O4N2 polyhedron, whereas complex IV contains the Cl2N2 polyhedron. Complexes I and IV were found to show a high catalytic activity in ethylene polymerization reaction.

  DOI：

  10.1134/s1070328407060097
• 作为产物：
  描述：

  2-肼基-4-甲基喹啉 在 溶剂黄146 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 3.0h， 生成 (3bS,4aR)3,4,4-trimethyl-1-(4-methylquinoline-2-yl)-3b,4,4a,5-tetrahydro-1H-cyclopropane[3,4]cyclopenta[1,2-c]pyrazole
  参考文献：
  名称：

  Synthesis of new chiral N-substituted fused pyrazoles and pyrazolinols

  摘要：

  Treatment of beta-diketones and the corresponding beta-enaminoketones, having modified carane (2-ethyl-6,6-dimethylbicyclo[3.1.0]hexane) and p-menthane (3-ethyl-1-isopropylcyclopentane) skeletons, with aryl-and alkylhydrazines results in regioselective formation of N-substituted pyrazoles or stable pyrazolinols depending on the nature of the substituent at the hydrazine nitrogen. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)10239-3

文献信息

• Fe(II) complex with chiral pyrazolylquinoline L and Fe(II), Co(II), and Cu(II) complexes with achiral pyrazolylquinoline L1: Synthesis and properties. The crystal structures of [ML1Cl2] (M = Fe, Co, and Cu)
  作者：Z. A. Savel’eva、L. A. Glinskaya、R. F. Klevtsova、S. A. Popov、A. V. Tkachev、N. V. Semikolenova、V. A. Zakharov、S. V. Larionov

  DOI：10.1134/s1070328408040076

  日期：2008.4

  The complexes FeLCl2 (I), [(FeLCl2)-Cl-1] (II), [(CoLCl2)-Cl-1] (III), and [(CuLCl2)-Cl-1] (IV) (where L and L-1 are chiral and achiral pyrazolylquinolines, respectively) were obtained. Complexes II-IV were structurally characterized by single-crystal X-ray diffraction analysis. Crystals of complexes II and III are triclinic (space group P) and crystals of complex IV are monoclinic (space group P2(1)/n). Structures II-IV are built from discrete mononuclear acentric molecules. In these complexes, the M2+ ion (M = Fe, Co, and Cu) coordinates two N atoms of the bidentate chelating ligand L-1 and two Cl atoms. The coordination cores MCl2N2 are distorted tetrahedra. For complexes I and II, mu(eff) = 5.05 and 5.07 mu(B), respectively, correspond to the high-spin configuration d(6). For complex III, mu(eff) = 4.51 mu(B) (high-spin configuration d(7)) and for complex IV, mu(eff) = 1.80 mu(B) (configuration d(9)).
• Chiral complexes of PdCl2 with hydroxypyrazolylquinoline and pyrazolylquinoline based on the monoterpenoid (+)-3-carene: Synthesis and structures
  作者：Z. A. Savel’eva、R. F. Klevtsova、L. A. Glinskaya、S. A. Popov、A. V. Tkachev、S. V. Larionov

  DOI：10.1134/s1070328410090083

  日期：2010.9

  The chiral complexes [(PdLCl2)-Cl-1] (I) and [(PdLCl2)-Cl-2] (II) (where L-1 and L-2 are hydroxypyrazolylquinoline and pyrazolylquinoline, respectively, based on the monoterpenoid (+)-3-carene) were obtained and examined using X-ray diffraction. The crystal structures of complexes I and II are built from mononuclear acentric molecules. The Pd2+ ions coordinate two N atoms of the chelating bidentate ligand L-1 or L-2 and two Cl atoms. The coordination polyhedron Cl2N2 is a square distorted in a tetrahedral manner. In structure I, adjacent molecules are linked by intermolecular contacts and hydrogen bonds Cl center dot center dot center dot H-O, which gives rise to chains aligned with the axis x. In structure II, contacts that are substantially shorter than the van der Waals interactions were not detected.
• Synthesis of new chiral N-substituted fused pyrazoles and pyrazolinols
  作者：Sergey A. Popov、Makhmut M. Shakirov、Alexey V. Tkachev、Norbert De Kimpe

  DOI：10.1016/s0040-4020(97)10239-3

  日期：1997.12

  Treatment of beta-diketones and the corresponding beta-enaminoketones, having modified carane (2-ethyl-6,6-dimethylbicyclo[3.1.0]hexane) and p-menthane (3-ethyl-1-isopropylcyclopentane) skeletons, with aryl-and alkylhydrazines results in regioselective formation of N-substituted pyrazoles or stable pyrazolinols depending on the nature of the substituent at the hydrazine nitrogen. (C) 1997 Elsevier Science Ltd.
• Cobalt(II) and copper(II) complexes with chiral pyrazolylquinoline, a derivative of terpenoid (+)-3-carene. Catalytic activity in ethylene polymerization reaction
  作者：S. V. Larionov、Z. A. Savel’eva、N. V. Semikolenova、R. F. Klevtsova、L. A. Glinskaya、E. G. Boguslavskii、V. N. Ikorskii、V. A. Zakharov、S. A. Popov、A. V. Tkachev

  DOI：10.1134/s1070328407060097

  日期：2007.6

  Coordination compounds [CoLCl2] (I), [CuLCl(NO3)] (II), CuL(NO3)(2) (III), and CuLCl2 (IV) (where L is a chiral pyrazolylquinoline - a derivative of terpenoid (+)-3-carene) were synthesized. X-ray diffraction data showed that crystal structures I and 11 are built of mononuclear acentric molecules. In the molecule of complex 1, the Co2+ ion coordinates two N atoms of bidentate cycle-forming ligand L and two Cl atoms. The coordination polyhedron of Cl2N2 is a distorted tetrahedron. For complex I, mu(eff) = 4.50 mu(B), which corresponds to a high-spin configuration d(7). In the molecules of II(1), II(2) (which are diastereoisomers of complex II), each Cu2+ ion coordinates two N atoms of bidentate cycle-forming ligand L, the Cl atom, and two O atoms of bidenlate cyclic NO3- ion. The ClN2O2 coordination polyhedra are tetragonal pyramids with different degrees of distortion . The structure of complex II consists of supramolecular clusters, i.e., isolated chains incorporating the molecules of II(1) and II(2). The values of mu(eff) for II-IV correspond to the d(9) configuration. The results of EPR and IR study suggest that complex III contains the O4N2 polyhedron, whereas complex IV contains the Cl2N2 polyhedron. Complexes I and IV were found to show a high catalytic activity in ethylene polymerization reaction.