2-(tert-butyldimethylsilanyloxy)phenyl isocyanate | 165405-44-7

• 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-(tert-butyldimethylsilanyloxy)phenyl isocyanate
• 英文别名: 2-(t-Butyldimethylsilyloxy)phenyl Isocyanate；tert-butyl-(2-isocyanatophenoxy)-dimethylsilane
• CAS: 165405-44-7
• 化学式: C₁₃H₁₉NO₂Si
• 分子量: 249.385
• InChiKey: LHOFJYAPEIQGGN-UHFFFAOYSA-N

物化性质

• 沸点：
  271.6±23.0 °C(Predicted)
• 密度：
  0.95±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.04
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(tert-butyldimethylsilanyloxy)phenyl isocyanate 在 四丁基氟化铵 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  1,3-Disubstituted benzazepines as neuropeptide Y Y1 receptor antagonists

  摘要：

  A nuclei, have been designed, synthesized, and evaluated for activity. Through a blind screening we found the compound 1-N-(3-(N'-(tert-butoxycarbonyl)amino)benzyl)-7-methoxy-(3-(3)-methylureido)-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one (9: IC50 = 1.6 mu M). Chemical modifications of 9 gave a potent NPY Y1 antagonist 3-(N-(4-hydroxyphenyl)-N'-methylguanidino)-1-N-(3-(N'-(tert-butoxycarbonyl)amino)benzyl)-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one (14c: IC50 = 43 nM), which had no affinity for NPY Y2 and Y5 receptors. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00087-5
• 作为产物：
  描述：

  2-氨基苯酚 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 16.0h， 生成 2-(tert-butyldimethylsilanyloxy)phenyl isocyanate
  参考文献：
  名称：

  新型1,2-地硫辛：合成，分子模型研究和抗真菌活性。

  摘要：

  本文报道了涉及1,2-二硫氨酸类化合物（1,2-二硫代环己二烯）的第一项结构活性研究。从双硫辛素1d和1e合成了一系列的3,6-二取代的1,2-二硫辛素，并作为抗真菌剂进行了评估。据报道，一种新的，多功能的二硫辛素1d和1e合成方法可以在千克水平上扩大规模。该方法的新颖性源于使用β-巯基丙腈作为亲硫试剂，它依赖于β-消除策略和随后的氧化作用以生成1,2-二硫辛环。通过分子力学和Hartree-Fock分子轨道计算确定了dithiins 1d，18i和45和模型dithiin 61的最佳几何形状。为1提供了两种可能的作用机制

  DOI：

  10.1021/jm00014a016

文献信息

• Preparation of symmetrical and unsymmetrical
  申请人：Shaman Pharmaceuticals, Inc.

  公开号：US05583235A1

  公开（公告）日：1996-12-10

  The present invention provides an improved procedure for the preparation of 3,6-disubstituted-1,2-dithiin derivatives, especially unsymmetrical 1,2-dithiins. In addition, the process offers significant process, scaleup, and safety advantages over the previously reported synthetic processes. The compounds synthesized by this new process and described herein are particularly effective in treating fungal infections, especially those caused by Candida albicans, Cryptococcus neoformans, Aspergillus fumigatus, Trichophyton rubrum, Candida parapsilosis, Candida tropicalis, or Candida krusei.

  本发明提供了一种改进的方法，用于制备3,6-二取代-1,2-二硫杂环衍生物，尤其是不对称的1,2-二硫杂环。此外，该方法相比先前报道的合成方法具有显著的工艺、放大和安全优势。由此新方法合成的化合物在治疗真菌感染方面特别有效，尤其是由白色念珠菌、新型隐球菌、烟曲霉、红色毛癣菌、副木霉、热带念珠菌或克鲁氏念珠菌引起的感染。
• 2-Nitrophenylcarbamoyl-(<i>S</i>)-prolyl-(<i>S</i>)-3-(2-naphthyl)alanyl-<i>N</i>-benzyl-<i>N</i>- methylamide (SDZ NKT 343), a Potent Human NK₁ Tachykinin Receptor Antagonist with Good Oral Analgesic Activity in Chronic Pain Models
  作者：C. Walpole、S. Y. Ko、M. Brown、D. Beattie、E. Campbell、F. Dickenson、S. Ewan、G. A. Hughes、M. Lemaire、J. Lerpiniere、S. Patel、L. Urban

  DOI：10.1021/jm970499g

  日期：1998.8.1

  A lead compound which had sub-micromolar affinity for the rabbit NK1 receptor but negligible affinity for rat NK1 receptors, 3a, was discovered by directed screening. 2-Substitution in the ring of the benzylthiourea substituent in the initial lead was found to be important, and halogens (Cl, Br) in this position were found to improve affinity for the human receptor. The activity of a series of 2-halo-substituted benzylthioureas was then optimized by modification of the proline diphenylmethyl amide, guided by a simple conceptual model based on structural overlay between these early antagonists and NK1 selective peptides. In this way, aromatic amino acid amides were identified which had improved affinity with respect to the starting diphenylmethyl (DPM) amides. The first sub-nanomolar ligand for the human NK1 receptor which arose from this series, 4af, combined a 2-chlorobenzylthiourea unit with a 2-naphthylalanine amide. Contemporaneously it was discovered that the benzylthiourea unit could be simplified to a phenylthiourea providing that an appropriate 2-substituent was also incorporated. Combination of these two series gave 2-NO2 phenylthiourea analogues which led directly to the analogous urea, 5f(2-nitrophenylcarbamoyl-(S)-prolyl-(S)-3-(2-naphthyl)alanyl-N-benzyl-N-methylamide, SDZ NKT 343), a highly potent ligand for the human NK1 receptor (K-i = 0.16 nM). In addition to its high in vitro potency, 5f proved to be a potent orally active analgesic in guinea pig models of chronic inflammatory and neuropathic pain. The nature of the 2-aryl substituent was found to be critical for oral activity in this series. Clinical evaluation of 5f as a novel analgesic agent is currently underway.