1,2-dimethyl-1H-indazolium-3-(N-4-trifluoromethylphenyl)amidate | 907604-06-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,2-dimethyl-1H-indazolium-3-(N-4-trifluoromethylphenyl)amidate
• CAS: 907604-06-2
• 化学式: C₁₇H₁₄F₃N₃O
• 分子量: 333.313
• InChiKey: RVQNOVUQCKRGOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.87
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  39.98
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1,2-dimethyl-1H-indazolium-3-(N-4-trifluoromethylphenyl)amidate 、 丁炔二酸二乙酯 以 乙腈 为溶剂， 以66%的产率得到diethyl 1,2-dimethyl-2'-oxo-1'-(4-trifluoromethylphenyl)-1,2-dihydrospiro[indazole-3,3'-1H-pyrrole]-4',5'-dicarboxylate
  参考文献：
  名称：

  Translation of Pseudo-Cross-Conjugation into Chemistry:  Cycloadditions of Mesomeric Betaines to the New Ring System Spiro[indazole-3,3‘-pyrrole]

  摘要：

  Indazolium-3-amidates (X-ray analysis), readily available on trapping the N-heterocyclic carbene indazol-3-ylidene with isocyanates, underwent [3 + 2]-cycloadditions with activated triple bonds to spiro[indazole-3,3'-pyrroles]. A combination of NMR techniques such as heteronuclear single quantum coherence (HSQC), heteronuclear multiple bond correlation (HMBC), nuclear Overhauser enhancement spectroscopy (NOESY), and H-1/N-15 correlations were applied to elucidate the structures of the cycloadducts.

  DOI：

  10.1021/jo062391r
• 作为产物：
  描述：

  1,2-dimethyl-1H-indazol-2-ium-3-carboxylate 、 4-三氟甲基苯基异氰酸酯 以 甲苯 为溶剂， 生成 1,2-dimethyl-1H-indazolium-3-(N-4-trifluoromethylphenyl)amidate
  参考文献：
  名称：

  Translation of Pseudo-Cross-Conjugation into Chemistry:  Cycloadditions of Mesomeric Betaines to the New Ring System Spiro[indazole-3,3‘-pyrrole]

  摘要：

  Indazolium-3-amidates (X-ray analysis), readily available on trapping the N-heterocyclic carbene indazol-3-ylidene with isocyanates, underwent [3 + 2]-cycloadditions with activated triple bonds to spiro[indazole-3,3'-pyrroles]. A combination of NMR techniques such as heteronuclear single quantum coherence (HSQC), heteronuclear multiple bond correlation (HMBC), nuclear Overhauser enhancement spectroscopy (NOESY), and H-1/N-15 correlations were applied to elucidate the structures of the cycloadducts.

  DOI：

  10.1021/jo062391r

文献信息

• Pseudo-Cross-Conjugated Mesomeric Betaines and <i>N</i>-Heterocyclic Carbenes of Indazole
  作者：Andreas Schmidt、Ariane Beutler、Tobias Habeck、Thorsten Mordhorst、Bohdan Snovydovych

  DOI：10.1055/s-2006-942367

  日期：2006.6

  betaines (PCCMB) and derivatives of the indazole alkaloid Nigellicin. They decarboxylate on heating to give intermediary N-heterocyclic carbenes of indazole that can be trapped with iso(thio)cyanates to amidates. Alternatively, 1.2-dimethylindazolium-3-amidates can be prepared starting from the corresponding 1H-indazol-3-carboxylic acid which is converted into its chloride, reacted with anilines and deprotonated

  1.2-Dimethylindazolium-3-carboxylates 是假交叉共轭内消旋甜菜碱 (PCCMB) 和吲唑生物碱 Nigellicin 的衍生物。它们在加热时脱羧，生成中间的吲唑 N-杂环卡宾，可以用异（硫）氰酸酯捕获酰胺化物。或者，可以从相应的 1H-吲唑-3-羧酸开始制备 1,2-二甲基吲唑鎓-3-酰胺，将其转化为氯化物，与苯胺反应并在阴离子交换树脂上去质子化。这些酰胺化物的杂枯烯部分是假交叉共轭内消旋甜菜碱的新代表，可以通过 N-杂环卡宾交换为 3,5-二氯苯基异氰酸酯。