3a,4,6,6a-tetrahydro-3H-furo[3,4-c]pyrazol-6-one | 54467-45-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3a,4,6,6a-tetrahydro-3H-furo[3,4-c]pyrazol-6-one
• 英文别名: 3,3a,4,6a-tetrahydrofuro[3,4-c]pyrazol-6-one；3,3a,4,6a-tetrahydro-furo[3,4-c]pyrazol-6-one；4-Oxo-3-oxa-6,7-diazabicyclo<3.3.0>-oct-6-en；Phygapltwmstet-uhfffaoysa-
• CAS: 54467-45-7
• 化学式: C₅H₆N₂O₂
• 分子量: 126.115
• InChiKey: PHYGAPLTWMSTET-UHFFFAOYSA-N

物化性质

• 熔点：
  109.5-110.5 °C(Solv: tetrahydrofuran (109-99-9))
• 沸点：
  291.4±29.0 °C(Predicted)
• 密度：
  1.82±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  51
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3a,4,6,6a-tetrahydro-3H-furo[3,4-c]pyrazol-6-one 在 2,4,6-三甲基吡啶 、 正己烷 、 溴 、 叔丁基锂 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 、 二氯甲烷 、 氯仿 、 正戊烷 为溶剂， 反应 28.52h， 生成 3-[(1S,2S)-1-hydroxy-2-methylbutyl]-4-methylfuran-2(5H)-one
  参考文献：
  名称：

  Bioactive butenolides from Streptomyces antibioticus TÜ 99: absolute configurations and synthesis of analogs

  摘要：

  The four furanones (butenolides) 1-4, which had been isolated from the fermentation broth of Streptomyces antibioticus TU 99 and in preliminary tests had been shown to be biologically active, were synthesized by reaction of the readily available furanones 9 or 16 with 2-methylpropanal or 2-methylbutanal. In addition, a series of analogs was prepared in a similar way from 16 using different aldehydes. The hitherto unknown absolute configurations of the natural products 1-4 as well as those of all the analogs prepared were determined with Mosher's NMR method and/or X-ray crystallography. Some of the compounds synthesized proved to be active in the quorum sensing system of Chromobacterium violaceum. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00483-6
• 作为产物：
  描述：

  重氮甲烷 、 2(5H)-呋喃酮 以 乙醚 为溶剂， 生成 3a,4,6,6a-tetrahydro-3H-furo[3,4-c]pyrazol-6-one
  参考文献：
  名称：

  4-Oxo-3-oxa-6,7-diazabicyclo[3.3.0]oct-6-ene and its isomerization

  摘要：

  DOI：

  10.1007/bf00469882

文献信息

• PAVLENKO, Z. I., XIMIYA I TEXNOL. FURAN. SOEDIN., KRASNODAR, 1982, 36-40
  作者：PAVLENKO, Z. I.

  DOI：——

  日期：——
• PELLETIER S. W.; DJARMATI Z.; LAJSIC S. D.; MICOVIC I. V.; YANG D. T. C., TETRAHEDRON <TETR-AB>, 1975, 31, NO 15, 1659-1665
  作者：PELLETIER S. W.、 DJARMATI Z.、 LAJSIC S. D.、 MICOVIC I. V.、 YANG D. T. C.

  DOI：——

  日期：——
• ——
  作者：Z. I. Tyukhteneva、L. A. Badovskaya

  DOI：10.1023/a:1020818116077

  日期：——

  Reactions of 3a,4,6,6a-tetrahydro-3H-furo[3,4-c]pyrazol-6-one with chlorine and bromine give the corresponding 2,6-dihydro-4H-furo[3,4-c]pyrazol-6-one hydrohalides. Hydrolysis of 3a,4,6,6a-tetrahydro-3H-furo[3,4-c]pyrazol-6-one is accompanied by oxidation of the dihydropyrazole ring to pyrazole and opening of the lactone ring.
• Bioactive butenolides from Streptomyces antibioticus TÜ 99: absolute configurations and synthesis of analogs
  作者：Gilles Grossmann、Marc Poncioni、Marc Bornand、Benoı̂t Jolivet、Markus Neuburger、Urs Séquin

  DOI：10.1016/s0040-4020(03)00483-6

  日期：2003.4

  The four furanones (butenolides) 1-4, which had been isolated from the fermentation broth of Streptomyces antibioticus TU 99 and in preliminary tests had been shown to be biologically active, were synthesized by reaction of the readily available furanones 9 or 16 with 2-methylpropanal or 2-methylbutanal. In addition, a series of analogs was prepared in a similar way from 16 using different aldehydes. The hitherto unknown absolute configurations of the natural products 1-4 as well as those of all the analogs prepared were determined with Mosher's NMR method and/or X-ray crystallography. Some of the compounds synthesized proved to be active in the quorum sensing system of Chromobacterium violaceum. (C) 2003 Elsevier Science Ltd. All rights reserved.
• 4-Oxo-3-oxa-6,7-diazabicyclo[3.3.0]oct-6-ene and its isomerization
  作者：Z. I. Pavlenko、L. A. Badovskaya、V. G. Kul'nevich

  DOI：10.1007/bf00469882

  日期：1977.12