(2-Dimethylamino-phenyl)-acetonitrile | 1000512-16-2

• 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: (2-Dimethylamino-phenyl)-acetonitrile
• 英文别名: 2-[2-(Dimethylamino)phenyl]acetonitrile
• CAS: 1000512-16-2
• 化学式: C₁₀H₁₂N₂
• mdl: MFCD09923695
• 分子量: 160.219
• InChiKey: ZAUZKWFIZISABW-UHFFFAOYSA-N

物化性质

• 沸点：
  282.9±23.0 °C(Predicted)
• 密度：
  1.042±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2-Dimethylamino-phenyl)-acetonitrile 在 sodium hydroxide 作用下， 生成 2-(2-(二甲胺基)苯基)乙酸
  参考文献：
  名称：

  Bisphosphonate Inhibition of the Exopolyphosphatase Activity of the Trypanosoma brucei Soluble Vacuolar Pyrophosphatase

  摘要：

  Trypanosoma brucei, the causative agent of African trypanosomiasis, contains a soluble, vacuolar pyrophosphatase, TbVSP1, not present in humans, which is essential for the growth of bloodstream forms in their mammalian host. Here, we report the inhibition of a recombinant TbVSP1 expressed in Escherichia coli by a panel of 81 bisphosphonates. The IC50 values were found to vary from similar to 2 to 850 mu M. We then used 3D QSAR (comparative molecular field and comparative molecular similarity index; CoMFA and CoMSIA) methods to analyze the enzyme inhibition results. The R-2 values for the experimental versus the QSAR-predicted activities were 0.78 or 0.61 for CoMFA and 0.79 or 0.68 for CoMSIA, for two different alignments. The root-mean-square (rms) pIC(50) error for the best CoMFA model was 0.41 for five test sets of five activity predictions, which translates to a factor of similar to 2.6 error in IC50 prediction. For CoMSIA, the rms pIC(50) error and error factors were 0.35 and 2.2, respectively. In general, the most active compounds contained both a single aromatic ring and a hydrogen bond donor feature. Thirteen of the more potent compounds were then tested in vivo in a mouse model of T. brucei infection. The most active compound in vivo provided a 40% protection from death with no apparent side effects, suggesting that further development of such compounds may be of interest.

  DOI：

  10.1021/jm058220g
• 作为产物：
  描述：

  2-氨基苯乙腈 、 碘甲烷 在 sodium hydride 作用下， 生成 (2-Dimethylamino-phenyl)-acetonitrile
  参考文献：
  名称：

  Bisphosphonate Inhibition of the Exopolyphosphatase Activity of the Trypanosoma brucei Soluble Vacuolar Pyrophosphatase

  摘要：

  Trypanosoma brucei, the causative agent of African trypanosomiasis, contains a soluble, vacuolar pyrophosphatase, TbVSP1, not present in humans, which is essential for the growth of bloodstream forms in their mammalian host. Here, we report the inhibition of a recombinant TbVSP1 expressed in Escherichia coli by a panel of 81 bisphosphonates. The IC50 values were found to vary from similar to 2 to 850 mu M. We then used 3D QSAR (comparative molecular field and comparative molecular similarity index; CoMFA and CoMSIA) methods to analyze the enzyme inhibition results. The R-2 values for the experimental versus the QSAR-predicted activities were 0.78 or 0.61 for CoMFA and 0.79 or 0.68 for CoMSIA, for two different alignments. The root-mean-square (rms) pIC(50) error for the best CoMFA model was 0.41 for five test sets of five activity predictions, which translates to a factor of similar to 2.6 error in IC50 prediction. For CoMSIA, the rms pIC(50) error and error factors were 0.35 and 2.2, respectively. In general, the most active compounds contained both a single aromatic ring and a hydrogen bond donor feature. Thirteen of the more potent compounds were then tested in vivo in a mouse model of T. brucei infection. The most active compound in vivo provided a 40% protection from death with no apparent side effects, suggesting that further development of such compounds may be of interest.

  DOI：

  10.1021/jm058220g

文献信息

• Efficient construction of diverse 3-cyanoindoles under novel tandem catalysis
  作者：Jun Wu、Jiabin Liu、Kerui Zhou、Zhenni He、Qian Wang、Fen Wu、Tingting Miao、Jinjie Qian、Qian Shi

  DOI：10.1039/d0cc05439a

  日期：——

  unprotected, N-alkyl and N-aryl 3-cyanoindoles are obtained with good to excellent yields. The usefulness of this synthetic approach is further demonstrated by the successful synthesis of practical compounds such as the therapeutic estrogen receptor ligand A precursor. Mechanism study shows that the tandem catalysis exploits a Suzuki cross-coupling with subsequent base-induced isoxazole fragmentation, followed

  已经开发了通过钯催化的串联反应的3-氰基吲哚的新颖和快速的构建。获得“ NH”无保护基的N-烷基和N-芳基3-氰基吲哚，收率为好至极好。这种合成方法的实用性通过成功合成实用化合物（例如治疗性雌激素受体配体A前体）得到进一步证明。机理研究表明，串联催化利用了Suzuki交叉偶联以及随后的碱诱导的异恶唑片段化，然后是醛亚胺缩合。
• Lanthanide-Catalyzed Tandem Addition of Amines to Cyanoalkenes: Synthesis of Cyclic Amidines
  作者：Jinsong Hou、Gaosheng Yang、Zhuo Chai

  DOI：10.1021/acs.joc.1c02481

  日期：2022.1.7

  A tandem insertion of aliphatic nitriles and unactivated alkenes to the N–H bond of secondary aliphatic amines catalyzed by simple trialkyl rare-earth metal complexes was disclosed. This reaction provides a highly atom-economic and stereoselective way to a range of cyclic amidines under mild reaction conditions.

  公开了由简单的三烷基稀土金属配合物催化的脂肪族腈和未活化烯烃串联插入脂肪族仲胺的 N-H 键。该反应在温和的反应条件下为一系列环状脒提供了一种高度原子经济和立体选择性的方法。
• Chemodivergent C(sp3)–H and C(sp2)–H cyanomethylation using engineered carbene transferases
  作者：Juner Zhang、Ailiena O. Maggiolo、Edwin Alfonzo、Runze Mao、Nicholas J. Porter、Nayla M. Abney、Frances H. Arnold

  DOI：10.1038/s41929-022-00908-x

  日期：——

  The ubiquity of C–H bonds presents an opportunity to efficiently elaborate and build complexity in organic molecules. Methods for selective functionalization, however, must differentiate among multiple, chemically similar C–H bonds: enzymes are attractive because they can be finely tuned using directed evolution to achieve divergent reaction outcomes. Here we present engineered enzymes that effect

  C-H 键的普遍存在为有效地阐述和构建有机分子的复杂性提供了机会。然而，选择性功能化的方法必须区分多个化学上相似的 C-H 键：酶之所以有吸引力，是因为它们可以使用定向进化进行微调，以实现不同的反应结果。在这里，我们提出了具有独特选择性的工程酶，可实现全新的 C–H 烷基化（C–H 卡宾插入）：基于细胞色素 P450 的卡宾转移酶将 α-氰基卡宾传递到 α-氨基 C( sp 3 ) -H键或N-取代芳烃的邻位芳烃C( sp 2 )-H键。这两种转化通过不同的机制进行，但只需要对蛋白质支架进行最小的改变来调整酶的化学选择性。 C( sp 3 )–H 烷基酶的结构研究揭示了活性位点螺旋破坏，与天然酶相比，这改变了底物结合袋的结构和静电。总的来说，这项工作展示了使用高度可调的酶作为 C-H 官能化催化剂进行不同分子衍生化的优势。
• Bleaching composition
  申请人：UNILEVER N.V.

  公开号：EP0464880A1

  公开（公告）日：1992-01-08

  Novel cationic nitriles, methods of preparing such nitriles and use thereof as cationic peroxyacid bleach precursor in bleaching (detergent) compositons are disclosed. The novel cationic nitriles are non-hygroscopic and are characterized in that they have a counter-anion X-selected from the group consisting of 1) R-SO3-, 2) R-SO4-, 3) R-CO2-, wherein R is a straight or branched chain, optionally substituted, alkyl, alkylether or alkylene group containing 4 to 20 carbon atoms, or a phenyl or alkyl phenyl group containing 6 to 20 carbon atoms, and 4) any other surfactant anion not falling under the groups 1), 2) and 3).

  本发明公开了新型阳离子腈类、制备此类腈类的方法及其在漂白（洗涤剂）组合物中作为阳离子过氧酸漂白剂前体的用途。 新型阳离子腈类无吸湿性，其特征在于它们具有从以下组成的组中选出的反阴离子 X：1）R-SO3-；2）R-SO4-；3）R-CO2-，其中 R 是直链或支链、任选取代的、含有 4 至 20 个碳原子的烷基、烷基醚或亚烷基，或含有 6 至 20 个碳原子的苯基或烷基苯基；以及 4）不属于 1）、2）和 3）组的任何其他表面活性剂阴离子。
• Identification Of A Nitrilase From B. Japonicum By Rational Genome Mining And Methods Of Use
  申请人：Zhu Dunming

  公开号：US20070178575A1

  公开（公告）日：2007-08-02

  The present disclosure relates to methods of rational genome mining. A method may include narrowing the number of clones that would otherwise need to be screened and/or identifying a gene with a desired catalytic activity. The disclosure also relates to a nitrile hydrolase from Bradyrhizobium japonicum USDA110 first identified by rational genome mining. In addition, the disclosure relates to nitrilase bll6402 and catalytically active variants capable of converting an α-hydroxy nitriles, a β-hydroxy nitrile and/or an α,ω-dinitrile to a carboxylic acid.