rac-(3S,3aS)-3-phenyl-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-2-carbothioamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: rac-(3S,3aS)-3-phenyl-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-2-carbothioamide
• 英文别名: (3R,3aR)-3-phenyl-3,3a,4,5-tetrahydrobenzo[g]indazole-2-carbothioamide
• 化学式: C₁₈H₁₇N₃S
• 分子量: 307.419
• InChiKey: XYIXNDFQNMYLLB-RDJZCZTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  73.7
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  rac-(3S,3aS)-3-phenyl-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-2-carbothioamide 在 三氟乙酸 作用下， 反应 45.0h， 以10%的产率得到rac-(3R,3aS)-3-phenyl-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-2-carbothioamide
  参考文献：
  名称：

  Isomerization of substituted tricyclic 4,5-dihydropyrazoles

  摘要：

  The acid and base catalyzed isomerization of some tricyclic 2-pyrazolines with N-Carbamoyl-, N-thiocarbamoyl- and N-phenyl substituents was investigated. Starting from cis or trans 3-H, 3a-H diastereomers, equilibrium mixtures of cis and tl ans diastereomers were prepared which were separated and subsequently studied by H-1 NMR and C-13 NMR spectroscopy. A mechanism for the isomerization of the pyrazolines is suggested, supported by a deuterium exchange at C-3a.

  DOI：

  10.1007/bf00807038
• 作为产物：
  描述：

  (E)-2-benzylidene-1-tetralone 、 氨基硫脲 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 以65%的产率得到rac-(3S,3aS)-3-phenyl-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-2-carbothioamide
  参考文献：
  名称：

  新型3,3a，4,5-四氢-2 H-苯并[ g ]吲唑-2-基-噻唑-4（5 H）-ones的合成，结构及抗菌性能评价

  摘要：

  的氨基脲或氨基硫脲与在碱性条件下，得到的3,3a 2-亚芳基-1-四氢萘酮，4,5-四氢-2反应ħ -苯并[克]吲唑-2-羰（硫代）酰胺作为混合物的顺式和3-H和3a-H的反式非对映异构体。报道了由顺式异构体和α-卤代酸的缩合反应合成新的吲唑基-噻唑-4（5 H）-酮。介绍了DFT研究以及代表性化合物的X射线单晶数据。筛选了所有八个新合成的吲唑基-噻唑-4（5 H）-的抗菌和抗真菌活性，某些化合物显示出令人鼓舞的活性。

  DOI：

  10.1016/j.saa.2014.06.134

文献信息

• 2-Substituted indazoles. Synthesis and antimicrobial activity
  作者：Tamás Lóránd、Béla Kocsis、Levente Emôdy、Pál Sohár

  DOI：10.1016/s0223-5234(99)00120-8

  日期：1999.11

  2-Isothiocarbamoyl substituted fused pyrazolines and their S-alkvl derivatives were prepared as potentially antimicrobial agents. Conventional methods were used to synthesize the novel derivatives starting from cyclic unsaturated ketones and thiosemicarbazide under acidic catalyst. These cyclizations yielded only one diastereoisomer of 3-H, 3a-H cis. The alkylations were performed applying alkyl halides. The structures of the new compounds, including configurations and conformations, were elucidated by NMR spectroscopy, also making use of 2D-HSC, DEFT and DNOE measurements. The S-alkyl derivatives were evaluated for activity against Gram-negative and Gram-positive bacteria and their in vitro toxicity was determined on HeLa cells. The structure-activity relationship was also studied. (C) 1999 Editions scientifiques et medicales Elsevier SAS.
• Synthesis, structure and antimicrobial evaluation of new 3,3a,4,5-tetrahydro-2H-benzo[g]indazol-2-yl-thiazol-4(5H)-ones
  作者：Deepika Gautam、R.P. Chaudhary

  DOI：10.1016/j.saa.2014.06.134

  日期：2015.1

  The reaction of semicarbazide or thiosemicarbazide with 2-arylidene-1-tetralones under alkaline condition affords 3,3a,4,5-tetrahydro-2H-benzo[g]indazole-2-carbo(thio)amides as a mixture of cis and trans diastereoisomers of 3-H and 3a-H. The synthesis of new indazolyl-thiazol-4(5H)-ones from the condensation of cis isomer and α-halo acids is reported. A DFT study along with X-ray single crystal data

  的氨基脲或氨基硫脲与在碱性条件下，得到的3,3a 2-亚芳基-1-四氢萘酮，4,5-四氢-2反应ħ -苯并[克]吲唑-2-羰（硫代）酰胺作为混合物的顺式和3-H和3a-H的反式非对映异构体。报道了由顺式异构体和α-卤代酸的缩合反应合成新的吲唑基-噻唑-4（5 H）-酮。介绍了DFT研究以及代表性化合物的X射线单晶数据。筛选了所有八个新合成的吲唑基-噻唑-4（5 H）-的抗菌和抗真菌活性，某些化合物显示出令人鼓舞的活性。
• Isomerization of substituted tricyclic 4,5-dihydropyrazoles
  作者：T. L�r�nd、F. Aradi、�. Sz�ll�sy、G. T�th、T. K�nya

  DOI：10.1007/bf00807038

  日期：——

  The acid and base catalyzed isomerization of some tricyclic 2-pyrazolines with N-Carbamoyl-, N-thiocarbamoyl- and N-phenyl substituents was investigated. Starting from cis or trans 3-H, 3a-H diastereomers, equilibrium mixtures of cis and tl ans diastereomers were prepared which were separated and subsequently studied by H-1 NMR and C-13 NMR spectroscopy. A mechanism for the isomerization of the pyrazolines is suggested, supported by a deuterium exchange at C-3a.