2,2-dimethyl-1-(6-nitro-benzotriazolyl)propane-1-thione | 220642-22-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: 2,2-dimethyl-1-(6-nitro-benzotriazolyl)propane-1-thione
• 英文别名: 1-thiopivaloyl-6-nitrobenzotriazole；2,2-Dimethyl-1-(6-nitrobenzotriazol-1-yl)propane-1-thione
• CAS: 220642-22-8
• 化学式: C₁₁H₁₂N₄O₂S
• 分子量: 264.308
• InChiKey: MYUGIWURERYGHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-1-(6-nitro-benzotriazolyl)propane-1-thione 在 lithium hydroxide 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 (S)-2-((4R,5R)-2-tert-Butyl-4-hydroxymethyl-4,5-dihydro-thiazol-5-yl)-propionic acid
  参考文献：
  名称：

  Synthesis of 2,4,5-trisubstituted thiazoline via a novel stereoselective intramolecular conjugate addition

  摘要：

  A convenient stereoselective preparation of 2,4,5-trisubstituted thiazolines is reported. The procedure involves the cyclisation of an unsaturated thioamide under mildly acidic conditions, and proceeds with excellent stereocontrol. A range of substrates are presented, and an explanation of the stereochemical outcome discussed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.04.029
• 作为产物：
  描述：

  pivalic acid isobutoxycarbonyl ester 在 tetraphosphorus decasulfide 、 sodium carbonate 、 sodium nitrite 作用下， 以 四氢呋喃 、 水 、 溶剂黄146 为溶剂， 反应 3.5h， 生成 2,2-dimethyl-1-(6-nitro-benzotriazolyl)propane-1-thione
  参考文献：
  名称：

  通过亚硫酰基硝基苯并三唑制得亚硫酸酯的一般有效途径。

  摘要：

  DOI：

  10.1021/jo981985u

文献信息

• Conformationally Constrained Analogues of Diacylglycerol (DAG). 25. Exploration of the <i>sn</i>-1 and <i>sn</i>-2 Carbonyl Functionality Reveals the Essential Role of the <i>sn</i>-1 Carbonyl at the Lipid Interface in the Binding of DAG-Lactones to Protein Kinase C
  作者：Ji-Hye Kang、Megan L. Peach、Yongmei Pu、Nancy E. Lewin、Marc C. Nicklaus、Peter M. Blumberg、Victor E. Marquez

  DOI：10.1021/jm050352m

  日期：2005.9.1

  Diacylglycerol (DAG) lactones with altered functionality (C=O -> CH2 or C=O -> C=S) at the sn-1 and sn-2 carbonyl pharmacophores were synthesized and used as probes to dissect the individual role of each carbonyl in the binding to protein kinase C (PKC). The results suggest that the hydrated sn-1 carbonyl is engaged in very strong hydrogen-bonding interactions with the charged lipid headgroups and organized water molecules at the lipid interface. Conversely, the sn-2 carbonyl has a more modest contribution to the binding process as a result of its involvement with the receptor (Cl domain) via conventional hydrogen bonding to the protein. The parent DAG-lactones, E-6 and Z-7, were designed to bind exclusively in the sn-2 binding mode to ensure the correct orientation and disposition of pharmacophores at the binding site.
• A General and Efficient Route to Thionoesters via Thionoacyl Nitrobenzotriazoles
  作者：M. Ashraf Shalaby、Henry Rapoport

  DOI：10.1021/jo981985u

  日期：1999.2.1
• Synthesis of 2,4,5-trisubstituted thiazoline via a novel stereoselective intramolecular conjugate addition
  作者：Zhengshuang Xu、Tao Ye

  DOI：10.1016/j.tetasy.2005.04.029

  日期：2005.6

  A convenient stereoselective preparation of 2,4,5-trisubstituted thiazolines is reported. The procedure involves the cyclisation of an unsaturated thioamide under mildly acidic conditions, and proceeds with excellent stereocontrol. A range of substrates are presented, and an explanation of the stereochemical outcome discussed. (c) 2005 Elsevier Ltd. All rights reserved.