[3-(chloromethyl)-2,4,6-trimethylphenyl]acetonitrile | 250651-08-2

• 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: [3-(chloromethyl)-2,4,6-trimethylphenyl]acetonitrile
• 英文别名: 2-[3-(Chloromethyl)-2,4,6-trimethylphenyl]acetonitrile
• CAS: 250651-08-2
• 化学式: C₁₂H₁₄ClN
• 分子量: 207.703
• InChiKey: GUPGZPGVTXWOOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  [3-(chloromethyl)-2,4,6-trimethylphenyl]acetonitrile 在 水 、 cadmium(II) acetate 、 三溴化磷 、 calcium carbonate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 N,N-二甲基甲酰胺 、 氯苯 为溶剂， 反应 195.0h， 生成 1-(3-{[(4S)-4-isopropyl-4,5-dihydrooxazol-2-yl]methyl}-2,4,6-trimethylbenzyl)-3-methylimidazolium bromide
  参考文献：
  名称：

  Imidazolium-Based Frameworks: Imidazolium Salt-Oxazoline/Palladium(II) Acetate In Situ Catalyst Systems

  摘要：

  通过三步法合成了新型简单咪唑啉类双齿配体前体，并通过两步法制备了双(恶唑啉)配体。利用铃木-宫浦反应来确定由恶唑啉基咪唑啉阳离子、双(恶唑啉)和乙酸钯(II)原位生成的钯(II)催化剂体系的活性。其中，两种立体阻碍的N-芳基咪唑啉阳离子在低催化剂体系负载下展示了其对芳基溴化物和氯化物的有效性。

  DOI：

  10.1055/s-2007-965938
• 作为产物：
  描述：

  2,4-双(氯甲基)三甲基苯 、 氰化钠 以 二甲基亚砜 为溶剂， 以34%的产率得到[3-(chloromethyl)-2,4,6-trimethylphenyl]acetonitrile
  参考文献：
  名称：

  Imidazolium-Based Frameworks: Imidazolium Salt-Oxazoline/Palladium(II) Acetate In Situ Catalyst Systems

  摘要：

  通过三步法合成了新型简单咪唑啉类双齿配体前体，并通过两步法制备了双(恶唑啉)配体。利用铃木-宫浦反应来确定由恶唑啉基咪唑啉阳离子、双(恶唑啉)和乙酸钯(II)原位生成的钯(II)催化剂体系的活性。其中，两种立体阻碍的N-芳基咪唑啉阳离子在低催化剂体系负载下展示了其对芳基溴化物和氯化物的有效性。

  DOI：

  10.1055/s-2007-965938

文献信息

• Endothelin Antagonists:  Substituted Mesitylcarboxamides with High Potency and Selectivity for ET_A Receptors
  作者：Chengde Wu、E. Radford Decker、Natalie Blok、Huong Bui、Qi Chen、B. Raju、Andree R. Bourgoyne、Vippra Knowles、Ronald J. Biediger、Robert V. Market、Shuqun Lin、Brian Dupré、Timothy P. Kogan、George W. Holland、Tommy A. Brock、Richard A. F. Dixon

  DOI：10.1021/jm9900063

  日期：1999.11.1

  We have previously disclosed the discovery of 2,4-disubstituted anilinothiophenesulfonamides with potent ETA-selective endothelin receptor antagonism and the subsequent identification of sitaxsentan (TBC11251, 1) as a clinical development compound (Wu et al. J. Med. Chem. 1997, 40, 1682 and 1690). The orally active 1 has demonstrated efficacy in a phase II clinical trial of congestive heart failure (Givertz ct al. Circulation 1998, 98, Abstr. #3044) and was active in rat models of myocardial infarction (Podesser et al. Circulation. 1998, 98, Abstr. #2896) and acute hypoxia-induced pulmonary hypertension (Chen et al. FASEB J. 1996, 10 (3), A104). We now report that an additional substituent at the 6-position of the anilino ring further increases the potency of this series of compounds. It was also found that a wide range of functionalities at the 3-position of the 2,4,6-trisubstituted ring increased ETA selectivity by similar to 10-fold while maintaining in vitro potency, therefore rendering the compounds amenable to fine-tuning of pharmacological and toxicological profiles with enhanced selectivity. The optimal compound in this series was found to be TBC2576 (7u), which has similar to 10-fold higher ETA binding affinity than 1, high ETA/ETB selectivity, and a serum half-life of 7.3 h in rats, as well as in vivo activity.
• Imidazolium-Based Frameworks: Imidazolium Salt-Oxazoline/Palladium(II) Acetate In Situ Catalyst Systems
  作者：Ermitas Alcalde、Neus Mesquida、Immaculada Dinarès、Sandra Rodríguez

  DOI：10.1055/s-2007-965938

  日期：2007.3

  New simple imidazolium-based bidentate ligand precursors were prepared by a three-step protocol and bis(oxazoline) ligands were prepared in two steps. A Suzuki-Miyaura reaction was utilized to ascertain the activity of a palladium(II) catalyst system generated in situ from an oxazolinyl-imidazolium cation, a bis(oxazoline), and palladium(II) acetate. Among them, two sterically hindered N-arylimidazolium cations demonstrated their efficiency with both aryl bromides and chlorides in low catalyst-system loading.

  通过三步法合成了新型简单咪唑啉类双齿配体前体，并通过两步法制备了双(恶唑啉)配体。利用铃木-宫浦反应来确定由恶唑啉基咪唑啉阳离子、双(恶唑啉)和乙酸钯(II)原位生成的钯(II)催化剂体系的活性。其中，两种立体阻碍的N-芳基咪唑啉阳离子在低催化剂体系负载下展示了其对芳基溴化物和氯化物的有效性。