2,3-diphenyl-2,4,5,6-tetrahydrocyclopenta[c]pyrazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2,3-diphenyl-2,4,5,6-tetrahydrocyclopenta[c]pyrazole
• 英文别名: 2,3-diphenyl-5,6-dihydro-4H-cyclopenta[c]pyrazole
• 化学式: C₁₈H₁₆N₂
• 分子量: 260.338
• InChiKey: ZJBOLGCJEXTJMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  二硫代苯甲酸甲酯 在 potassium tert-butylate 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 5.0h， 生成 2,3-diphenyl-2,4,5,6-tetrahydrocyclopenta[c]pyrazole
  参考文献：
  名称：

  Cyclocondensation of Arylhydrazines with 1,3-Bis(het)arylmonothio-1,3-diketones and 1,3-Bis(het)aryl-3-(methylthio)-2-propenones: Synthesis of 1-Aryl-3,5-bis(het)arylpyrazoles with Complementary Regioselectivity

  摘要：

  Two efficient highly regioselective routes for the synthesis of unsymmetrically substituted 1-aryl-3,5-bis(het)arylpyrazoles with complementary regioselectivity starting from active methylene ketones have been reported. In the first protocol, the newly synthesized 1,3-bis(het)aryl-monothio-1,3-diketone precursors (prepared by condensation of active methylene ketones with het(aryl) dithioesters in the presence of sodium hydride) were reacted with arylhydrazines in refluxing ethanol under neutral conditions, furnishing 1-aryl-3,5-bis(het)arylpyrazoles 7, in which the het(aryl) moiety attached to the thiocarbonyl group of monothio-1,3-diketones is installed at the 3-position. In the second method, the corresponding 3-(methylthio)-1,3-bis(het)aryl-2-propenones (prepared in situ by base-induced alkylation of 1,3-monothiodiketones) were condensed with arylhydrazines in the presence of potassium tert-butoxide in. refluxing tert-butyl alcohol, yielding 1-aryl-3,5-bis(het)arylpyrazoles 9 with complementary regioselectivity (method A). The efficiency of this protocol was further improved by developing a one-pot, three-component procedure for the synthesis of pyrazoles 9, directly from active methylene ketones, by reacting in situ generated 3-(methylthio)-1,3-bis(het)aryl-2-propenones with arylhydrazines in the presence of sodium hydride (instead of potassium tert-butoxide as base). The structures and regiochemistry of newly synthesized pyrazoles were confirmed from their spectral and analytical data along with X-ray crystallographic data of three pairs of regioisomers.

  DOI：

  10.1021/jo400599e

文献信息

• 1,3-Diarylcycloalkanopyrazoles and diphenyl hydrazides as selective inhibitors of cyclooxygenase-2
  作者：Zhihua Sui、Jihua Guan、Michael P. Ferro、Kathy McCoy、Michael P. Wachter、William V. Murray、Monica Singer、Michele Steber、Dave M. Ritchie、Dennis C. Argentieri

  DOI：10.1016/s0960-894x(00)00041-x

  日期：2000.3

  cyclooxygenase-2. The 1,3-diaryl substitution pattern of the pyrazole ring in 1 differentiates these compounds from most of the known selective COX-2 inhibitors that contain two aryl rings at the adjacent positions on a heterocyclic or a phenyl ring. Similarly, the two phenyl rings in 2 are also separated by three atoms. SAR of both phenyl rings in 1 and 2, and the aliphatic ring in 1 will be discussed.

  新型1，3-二芳基环烷吡唑1和二苯酰肼2被鉴定为环氧合酶2的选择性抑制剂。吡唑环中1的1,3-二芳基取代模式将这些化合物与大多数已知的选择性COX-2抑制剂区分开，这些抑制剂在杂环或苯环的相邻位置包含两个芳基环。类似地，2中的两个苯环也被三个原子隔开。将讨论1和2中两个苯环和1中脂族环的SAR。
• Regioselective synthesis of 1,3,4,5-tetrasubstituted pyrazoles from Baylis–Hillman adducts
  作者：Ka Young Lee、Jeong Mi Kim、Jae Nyoung Kim

  DOI：10.1016/s0040-4039(03)01648-4

  日期：2003.8

  Tetrasubstituted pyrazole derivatives 3a-j were synthesized regioselectively in good yields from the reaction of Baylis-Hillman adducts 1a-f and hydrazine hydrochlorides 2a-d in 1,2-dichloroethane. (C) 2003 Elsevier Ltd. All rights reserved.