2,6-Dichlorbenzylisothiocyanat | 31162-19-3

• 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: 2,6-Dichlorbenzylisothiocyanat
• 英文别名: 1,3-Dichloro-2-(isothiocyanatomethyl)benzene
• CAS: 31162-19-3
• 化学式: C₈H₅Cl₂NS
• 分子量: 218.106
• InChiKey: HPZAHNYYXILZIW-UHFFFAOYSA-N

物化性质

• 沸点：
  309.9±27.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  44.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,6-Dichlorbenzylisothiocyanat 生成 3-(2.6-Dichlorphenyl)-1.1.3.3-tetrachlor-2-azapropen-(1)
  参考文献：
  名称：

  Holtschmidt,H. et al., Justus Liebigs Annalen der Chemie, 1967, vol. 701, p. 107 - 116

  摘要：

  DOI：

文献信息

• Chiral Bifunctional Thiourea-Phosphane Organocatalysts in Asymmetric Allylic Amination of Morita-Baylis-Hillman Acetates
  作者：Hong-Ping Deng、Yin Wei、Min Shi

  DOI：10.1002/ejoc.201001660

  日期：2011.4

  A series of new chiral bifunctional thiourea-phosphane catalysts was synthesized and successfully applied in the catalytic, asymmetric allylic amination of Morita-Baylis-Hillman (MBH) acetates derived from the methyl vinyl ketone (MVK) or ethyl vinyl ketone (EVK) system, with phthalimide, affording the amination products in up to over 99 % yield and 90 % ee for a wide range of substrates derived from

  合成了一系列新型手性双官能硫脲-磷烷催化剂，并成功应用于甲基乙烯基酮（MVK）或乙基乙烯基酮（EVK）体系衍生的 Morita-Baylis-Hillman（MBH）乙酸酯的催化不对称烯丙基胺化反应，使用邻苯二甲酰亚胺，对于衍生自不同芳香醛的各种底物，胺化产物的产率高达 99% 以上，ee 高达 90%。
• Antimicrobial activity of a series of aminoalkyl esters of benzyldithiocarbamic acids
  作者：Robert C. Tweit、Robert D. Muir、Seth Mizuba

  DOI：10.1021/jm00302a043

  日期：1969.3
• 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.