2,2,2-trichloro-N-(pent-1-en-3-yl)acetamide

• 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: 2,2,2-trichloro-N-(pent-1-en-3-yl)acetamide
• 英文别名: N-(pent-4-en-3-yl)-2,2,2-trichloroacetamide；2,2,2-trichloro-N-pent-1-en-3-ylacetamide
• 化学式: C₇H₁₀Cl₃NO
• 分子量: 230.522
• InChiKey: AFFKPIZDOUYJHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,2,2-trichloro-N-(pent-1-en-3-yl)acetamide 在 tris(triphenylphosphine)ruthenium(II) chloride 、 偶氮二异丁腈 、 三正丁基氢锡 、 氯化铵 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 20.0h， 生成
  参考文献：
  名称：

  2-Iminopyrrolidines as Potent and Selective Inhibitors of Human Inducible Nitric Oxide Synthase

  摘要：

  A series of substituted 2-iminopyrrolidines has been prepared and shown to be potent and selective inhibitors of the human inducible nitric oxide synthase (hiNOS) isoform versus the human endothelial nitric oxide synthase (heNOS) and the human neuronal nitric oxide synthase (hnNOS). Simple substitutions at the 3-, 4-, or 5-position afforded more potent analogues than the parent 2-iminopyrrolidine 1. The effect of ring substitutions on both potency and selectivity for the different NOS isoforms is described. Substitution at the 4- and 5-positions of the 2-iminopyrrolidine yielded both potent and selective inhibitors of hiNOS. In particular, (+)-cis-4-methyl-5-pentylpyrrolidin-2-imine, monohydrochloride (20), displayed potent inhibition of hiNOS (IC50 = 0.25 mu M) and selectivities of 897 (heNOS IC50/hiNOS IC50) and 13 (hnNOS IC50/hiNOS IC50) Example 20 was shown to be an efficacious inhibitor of NO production in the mouse endotoxin assay. Furthermore, 20 displayed in vivo selectivity, versus heNOS isoform, by not elevating blood pressure at multiples of the effective dose in the mouse.

  DOI：

  10.1021/jm970840x
• 作为产物：
  描述：

  1-(1-imino-2,2,2-trichloroethoxy)-2(E)-pentene 在 gold(I) chloride 作用下， 以 水 为溶剂， 反应 2.0h， 以107 mg的产率得到2,2,2-trichloro-N-(pent-1-en-3-yl)acetamide
  参考文献：
  名称：

  Highly efficient gold(I)-catalyzed Overman rearrangement in water

  摘要：

  报道了一种高效的金(I)催化的Overman重排反应，将烯丙基三氯乙酰亚胺酯转化为烯丙基三氯乙酰胺。该反应在水中进行，具有环境友好和可扩展性的特点，通过这种方法成功地合成了一系列C3-烷基取代的烯丙基三氯乙酰胺，收率良好。

  DOI：

  10.3762/bjoc.7.88

文献信息

• Multifaceted catalysis approach to nitrile activation: direct synthesis of halogenated allyl amides from allylic alcohols
  作者：Roy P. Lester、Jay J. Dunsford、Jason E. Camp

  DOI：10.1039/c3ob41692e

  日期：——

  Allyl amides were synthesised from the reaction of allyl alcohols and halogenated nitriles using a platinum multifaceted catalysis approach in which both the nucleophilic addition and subsequent [3,3]-sigmatropic rearrangement steps of the process were catalysed by the same complex. Additionally, 1H/13C1H} NMR and GC studies provided the first insights into the mechanism of this transformation.

  使用铂多面催化方法从烯丙醇与卤化腈的反应中合成烯丙基酰胺，其中该过程的亲核加成和随后的[3,3]-σ重排步骤均由相同的配合物催化。此外，1 H / 13 C 1 H} NMR和GC研究提供了对该转化机理的初步见解。
• 2-Iminopyrrolidines as Potent and Selective Inhibitors of Human Inducible Nitric Oxide Synthase
  作者：Timothy J. Hagen、Arija A. Bergmanis、Steven W. Kramer、Kam F. Fok、Albert E. Schmelzer、Barnett S. Pitzele、Lydia Swenton、Gina M. Jerome、Christine M. Kornmeier、William M. Moore、Linda F. Branson、Jane R. Connor、Pamela T. Manning、Mark G. Currie、E. Ann Hallinan

  DOI：10.1021/jm970840x

  日期：1998.9.1

  A series of substituted 2-iminopyrrolidines has been prepared and shown to be potent and selective inhibitors of the human inducible nitric oxide synthase (hiNOS) isoform versus the human endothelial nitric oxide synthase (heNOS) and the human neuronal nitric oxide synthase (hnNOS). Simple substitutions at the 3-, 4-, or 5-position afforded more potent analogues than the parent 2-iminopyrrolidine 1. The effect of ring substitutions on both potency and selectivity for the different NOS isoforms is described. Substitution at the 4- and 5-positions of the 2-iminopyrrolidine yielded both potent and selective inhibitors of hiNOS. In particular, (+)-cis-4-methyl-5-pentylpyrrolidin-2-imine, monohydrochloride (20), displayed potent inhibition of hiNOS (IC50 = 0.25 mu M) and selectivities of 897 (heNOS IC50/hiNOS IC50) and 13 (hnNOS IC50/hiNOS IC50) Example 20 was shown to be an efficacious inhibitor of NO production in the mouse endotoxin assay. Furthermore, 20 displayed in vivo selectivity, versus heNOS isoform, by not elevating blood pressure at multiples of the effective dose in the mouse.
• Highly efficient gold(I)-catalyzed Overman rearrangement in water
  作者：Dong Xing、Dan Yang

  DOI：10.3762/bjoc.7.88

  日期：——

  A highly efficient gold(I)-catalyzed Overman rearrangement of allylic trichloroacetimidates to allylic trichloroacetamides in water is reported. With this environmentally benign and scalable protocol, a series of C3-alkyl substituted allylic trichloroacetamides were synthesized in good to high yields.

  报道了一种高效的金(I)催化的Overman重排反应，将烯丙基三氯乙酰亚胺酯转化为烯丙基三氯乙酰胺。该反应在水中进行，具有环境友好和可扩展性的特点，通过这种方法成功地合成了一系列C3-烷基取代的烯丙基三氯乙酰胺，收率良好。