2,2,2-trichloro-N¹,N¹,N²-trimethylacetamidine | 60523-35-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2,2,2-trichloro-N¹,N¹,N²-trimethylacetamidine
• 英文别名: Trichlor-N,N,N'-trimethylacetamidin；2,2,2-trichloro-N,N,N'-trimethylethanimidamide
• CAS: 60523-35-5
• 化学式: C₅H₉Cl₃N₂
• 分子量: 203.499
• InChiKey: DBLXYMCQTQVEHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  15.6
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,2,2-trichloro-N¹,N¹,N²-trimethylacetamidine 、 trimethoxonium tetrafluoroborate 生成 Trichlor-N,N,N',N'-tetramethylacetamidinium
  参考文献：
  名称：

  Kantlehner,W. et al., Liebigs Annalen der Chemie, 1979, p. 1354 - 1361

  摘要：

  DOI：
• 作为产物：
  描述：

  Trichlor-N,N,N'-trimethylacetamidinium 在 三乙胺 作用下， 生成 2,2,2-trichloro-N¹,N¹,N²-trimethylacetamidine
  参考文献：
  名称：

  Kantlehner,W. et al., Liebigs Annalen der Chemie, 1979, p. 1354 - 1361

  摘要：

  DOI：

文献信息

• Latent Nucleophilic Carbenes
  作者：Anatoliy Marchenko、Georgyi Koidan、Anastasiya Hurieva、Kostiantyn Shvydenko、Alexander B. Rozhenko、Eduard B. Rusanov、Andrii A. Kyrylchuk、Aleksandr Kostyuk

  DOI：10.1021/acs.joc.1c02397

  日期：2022.1.7

  functional groups, such as CHO, COR, and CN at double or triple bonds, displaying high mobility of the trimethylsilyl group. The obtained silylformamidine can be considered as a latent nucleophilic carbene. It can be prepared in bulk quantities, stored, and used when the need arises. Calculation results predict similar behavior for some other silylated formamidines and related compounds.

  使用 DFT 和 ab initio 计算，我们证明了非环状甲脒可以在相当温和的条件下进行热重排成它们的异构氨基卡宾。我们合成了甲硅烷基甲脒，预测了该过程中最低的活化能。实验研究证明它是一种非常活泼的亲核卡宾。与乙炔、苯和三氟甲烷的反应通过插入 sp、sp 2和 sp 3 进行CH 键。卡宾还与官能团（如 CHO、COR 和 CN）以双键或三键反应，显示出三甲基甲硅烷基的高迁移率。得到的甲硅烷基甲脒可视为潜在的亲核卡宾。它可以大批量制备、储存和在需要时使用。计算结果预测了一些其他甲硅烷基化甲脒和相关化合物的类似行为。
• Trichloroacetamidines, a new class of positive inotropic agents
  作者：Walfred S. Saari、Mark B. Freedman、Joel R. Huff、Stella W. King、Andrew W. Raab、Susan J. Bergstrand、Edward L. Engelhardt、Alexander Scriabine、George Morgan

  DOI：10.1021/jm00210a021

  日期：1978.12

  A series of trichloroacetamidine derivatives, obtained by addition of amines to trichloroacetonitrile, was evaluated for positive inotropic activity on isolated cat heart papillary muscles. Increased contractility, not antagonized by beta-adrenergic blockade with sotalol or reserpine pretreatment, was observed in this assay with a variety of N-substituted trichloroacetamidine derivatives. More extensive pharmacological studies with the 3-indolylmethyl analogue 2 showed that this amidine in dogs, 5 mg/kg iv, produced a positive inotropic effect more pronounced than that of ouabain, 50 microgram/kg iv. Several of the trichloroacetamidines were found to be inhibitors of guinea pig kidney and calf heart Na-K-dependent ATPase and to have specificity for these enzymes different from that of ouabain. Bacterial mutagenic activity was observed with three members, 2,3, and 12, of the series.
• Sinitsa, A. D.; Krishtal', V. S.; Kal'chenko, V. I., Journal of general chemistry of the USSR, 1980, vol. 50, # 10, p. 1943 - 1946
  作者：Sinitsa, A. D.、Krishtal', V. S.、Kal'chenko, V. I.、Markovskii, L. N.

  DOI：——

  日期：——
• Kantlehner,W. et al., Liebigs Annalen der Chemie, 1979, p. 1354 - 1361
  作者：Kantlehner,W. et al.

  DOI：——

  日期：——