syn-(methyl,chloro)bimane | 68654-19-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并吡唑类
• 英文名称: syn-(methyl,chloro)bimane
• 英文别名: 2,6-Dichloro-1,7-dimethylpyrazolo[1,2-a]pyrazole-3,5-dione
• CAS: 68654-19-3
• 化学式: C₈H₆Cl₂N₂O₂
• 分子量: 233.054
• InChiKey: KFPXZZNCTKCXSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  syn-(methyl,chloro)bimane 在 palladium on activated charcoal 氢气 、 potassium acetate 作用下， 以 溶剂黄146 为溶剂， 反应 4.0h， 以55%的产率得到syn-(methyl,hydro)bimane
  参考文献：
  名称：

  Bimanes. 5. Synthesis and properties of syn- and anti-1,5-diazabicyclo[3.3.0]octadienediones (9,10-dioxabimanes)

  摘要：

  DOI：

  10.1021/ja00535a028
• 作为产物：
  描述：

  3-methyl-4,4-dichloro-2-pyrazolin-5-one 以30%的产率得到
  参考文献：
  名称：

  KOSOWER H. E.; PAZHENCHERSKY B.; HERSHKOWITZ E., J. AMER. CHEM. SOC., 1978, 100, NO 20, 6516-6518

  摘要：

  DOI：

文献信息

• Bimanes. 23. The synthesis and properties of vinyl-9,10-dioxabimanes
  作者：Edward M. Kosower、David Zbaida、Michel Baud'huin、Daniele Marciano、Israel Goldberg

  DOI：10.1021/ja00176a034

  日期：1990.9

  Syntheses and useful reactions of syn-vinylbimanes are reported. The precursors are syn-(ethyl,methyl)bimane (4,6-diethyl-3,7-dimethyl-1,5-diazabicyclo[3.3.0]octa-3,6-diene-2,8-dione) (syn-(CH 3 CH 2 ,CH 3 )B) (2) and syn-(ethyl,chloro)bimane (4,6-diethyl-3,7-dichloro-1,5-diazabicyclo[3.3.0]octa-3,6-diene-2,8-dione) (syn-(CH 3 CH 2 ,Cl)B) (4)

  合成和有用的合成-乙烯基二甲胺的反应已被报道。前体是syn-(ethyl,methyl)bimane (4,6-diethyl-3,7-dimethyl-1,5-diazabicyclo[3.3.0]octa-3,6-diene-2,8-dione) (syn -(CH 3 CH 2 ,CH 3 )B) (2) 和syn-(ethyl,chloro)bimane (4,6-diethyl-3,7-dichloro-1,5-diazabicyclo[3.3.0]octa-3 ,6-diene-2,8-dione) (syn-(CH 3 CH 2 ,Cl)B) (4)
• Bimanes. 17. (Haloalkyl)-1,5-diazabicyclo[3.3.O]octadienediones (halo-9,10-dioxabimanes): reactivity toward the tripeptide thiol, glutathione
  作者：Annette E. Radkowsky、Edward M. Kosower

  DOI：10.1021/ja00275a045

  日期：1986.7
• Bimane cyclic esters, possible stereologues of trypanothione as antitrypanosomal agents. Bimanes 29
  作者：EM Kosower、AE Radkowsky、AH Fairlamb、SL Croft、RA Neal

  DOI：10.1016/0223-5234(96)88283-3

  日期：1995.1

  Tricyclic esters derived from bimanes have been synthesized with ring sizes near or equal to that of trypanothione disulfide (T(S)(2)), a bis-glutathionylspermidine that is involved in regulating the thiol status of Leishmania and other trypanosomatids. Modest activity for many of the compounds against Leishmania donovani with a maximum at the T(S)(2) ring size suggests that the esters act as T(S)(2) surrogates. However, no inhibition of T(S)(2)-reductase is observed for a number of the compounds. A series of tricyclic bimane amides with structures more closely analogous to T(S)2 are inactive in biological tests, New approaches were developed for the synthesis of the amides. The surprising effectiveness of the cyclic ester synthesis is explained. Acid chloride formation catalyzed by sulfides is briefly described.
• Bimanes. 15. Kinetics and mechanism of the hydroxide ion reaction with 1,5-diazabicyclo[3.3.0]octadienediones (9,10-dioxabimanes)
  作者：Hannah Kanety、Edward M. Kosower

  DOI：10.1021/jo00143a009

  日期：1982.10
• Bimane Acetylenes and Diacetylenes. Bimanes. 33
  作者：Edward M. Kosower、Marcia Ben-Shoshan

  DOI：10.1021/jo951830b

  日期：1996.1.1

  Two series (4,6-dihydro and 4,6-dimethyl) of syn-bimanes [1,5-diazabicyclo[3.3.0]octa-3,6-diene-2,8-diones] have been converted to acetylene and diacetylene derivatives. Their chemical and photophysical properties are reported. The 3-(and 6-)iodo (diiodo) derivatives are the best choices for Stille or Heck condensations with acetylenes or acrylates. Desilylation of (trimethylsilyl)acetylenes is best carried out with silver nitrate followed by lithium bromide. The acetylenes and diacetylenes are quite stable and highly fluorescent and represent candidate units for incorporation into polymers.