rac-(5S,6R,7S)-6-nitro-5,7-diphenyltetrahydro-1H,5H-pyrazolo[1,2-a]pyrazol-1-one | 72475-35-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: rac-(5S,6R,7S)-6-nitro-5,7-diphenyltetrahydro-1H,5H-pyrazolo[1,2-a]pyrazol-1-one
• 英文别名: (5R,6S,7R)-6-nitro-5,7-diphenyl-2,5,6,7-tetrahydro-1H-pyrazolo[1,2-a]pyrazol-3-one
• CAS: 72475-35-5；72521-96-1；103477-04-9
• 化学式: C₁₈H₁₇N₃O₃
• 分子量: 323.351
• InChiKey: PSWDHMXMFUDSDV-KURKYZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  69.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  rac-(5S,6R,7S)-6-nitro-5,7-diphenyltetrahydro-1H,5H-pyrazolo[1,2-a]pyrazol-1-one 在 劳森试剂 作用下， 以 苯 为溶剂， 反应 5.0h， 以90%的产率得到r-1-phenyl-c-2-nitro-t-3-phenyl-5-thioxoperhydropyrazolo<1,2-a>pyrazol
  参考文献：
  名称：

  A New Type of Highly Polar 1,3-Dipoles. Synthesis and Chemistry of Thiocarbonyl-stabilized Pyrazolidinazomethineimies

  摘要：

  3-Thioxopyrazolidine-azomethineimines (2) are synthesized from their 3-oxo analogues (1) and Lawesson's reagent (LR). The electron structures of 1 and 2 resemble those of polymethines, dipole moments of 2 are even higher than those of 1; further physical organic data are discussed. With NaBH4 2 gives 3-thioxopyrazolidines (8). These are S-mono- (10) and (N-1), S-bisalkylated (11). S-Alkylation of 2 affords pyrazolinium salts (7). 1,3-Dipolar cycloaddition of enamines to 2 results in [pi4s +pi2s] products (12, 13), HOMO/LUMO energies of 1 and 2 are given. Models of gamma-thiolactams (17, 19), mimicing antibiotics, are gained via 1,3-dipolar cycloadducts of 1 with LR.

  DOI：

  10.3987/com-94-6746
• 作为产物：
  描述：

  rac-(5S,6R,7S)-5-(4-chlorophenyl)-6-nitro-7-phenyltetrahydro-1H,5H-pyrazolo[1,2-a]pyrazol-1-one 以 氯仿 、 二甲基亚砜 为溶剂， 反应 48.0h， 生成 rac-(5S,6R,7S)-6-nitro-5,7-diphenyltetrahydro-1H,5H-pyrazolo[1,2-a]pyrazol-1-one
  参考文献：
  名称：

  Catalyst-Free and Stereoselective Synthesis of N,N-Bicyclic Pyrazolidinone Derivatives

  摘要：

  A catalyst-free and stereoselective cycloaddition of pyrazolidin-3-one-derived azomethine imine to trans-beta-nitrostyrene is described, which allows versatile, efficient and highly enantioselective synthesis of N,N-bicyclic pyrazolidinone derivatives.

  DOI：

  10.1055/s-0032-1316890

文献信息

• Are any non-stereospecific 1,3-dipolar cycloadditions known? A revision
  作者：Rolf Huisgen、Rudolf Weinberger

  DOI：10.1016/s0040-4039(00)98877-4

  日期：1985.1

  The cycloaddition of 1-benzylidenepyrazolid-3-one betaine to (E)-β-nitrostyrene, which has been claimed to furnish 15–30% non-stereospecific product, revealed stereospecificity up to 99.92% in a renewed study; (Z)-β-nitrostyrene stereoisomerizes under the influence of the 1,3-dipole.

  1-苄基吡唑并-3-酮甜菜碱与（E） -β-硝基苯乙烯的环加成反应，据称可提供15-30％的非立体特异性产物，在一项新的研究中显示其立体特异性高达99.92％。（Z） -β-硝基苯乙烯在1，3-偶极子的影响下立体异构化。
• 1,3-Dipolar cycloaddition of pyrazolid-3-one azomethinimines and E-β-nitrostyrene - elucidation of the generation of seemingly “non cisoid” adducts
  作者：Helmut Dorn

  DOI：10.1016/s0040-4039(00)98878-6

  日期：1985.1
• DORN H.; OZEGOWSKI R.; GRUENDEMANN E., J. PRAKT. CHEM., 1979, 321, NO 4, 555-564
  作者：DORN H.、 OZEGOWSKI R.、 GRUENDEMANN E.

  DOI：——

  日期：——
• HUISGEN, R.;WEINBERGER, R., TETRAHEDRON LETT., 1985, 26, N 42, 5119-5122
  作者：HUISGEN, R.、WEINBERGER, R.

  DOI：——

  日期：——
• DORN, H., TETRAHEDRON LETT., 1985, 26, N 42, 5123-5126
  作者：DORN, H.

  DOI：——

  日期：——