2-phenyl-4-(D-threo-1',2',3'-trihydroxypropyl)-2H-1,2,3-triazole | 15476-33-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-phenyl-4-(D-threo-1',2',3'-trihydroxypropyl)-2H-1,2,3-triazole
• 英文别名: D-xylose phenylozotriazol；(1R,2R)-1-(2-phenyl-2H-[1,2,3]triazol-4-yl)-propane-1,2,3-triol；(1R,2R)-1-(2-Phenyl-2H-[1,2,3]triazol-4-yl)-propan-1,2,3-triol；D-threo-Pentulose-phenylosotriazol, 4--2-phenyl-1,2,3-triazol；(1R,2R)-1-(2-phenyltriazol-4-yl)propane-1,2,3-triol
• CAS: 15476-33-2
• 化学式: C₁₁H₁₃N₃O₃
• 分子量: 235.243
• InChiKey: BAAINTSMEYOAIX-GHMZBOCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  91.4
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-phenyl-4-(D-threo-1',2',3'-trihydroxypropyl)-2H-1,2,3-triazole 在 三(二甲胺基)膦 作用下， 以 1,4-二氧六环 、 苯 为溶剂， 以49%的产率得到3-(2'-phenyl-1',2',3'-triazolyl-4')-2,6,7-trioxa-1-phosphabicyclo[2.2.1]heptan
  参考文献：
  名称：

  SYNTHESIS AND STRUCTURE OF SOME STABLE PHOSPHOLANE-PHOSPHOLANES

  摘要：

  Bicyclophosphites based on Linear 1,2,3-triols with terminal substituents were found to be stable. Thus a series of hitherto unknown phospholane-phospholane esters, including optically active ones, was synthesized and their promise for synthetic use was demonstrated. The structure of the new compounds was proved by H-1, C-13 and P-31 NMR spectroscopy and, for one of them, by X-ray analysis.

  DOI：

  10.1080/10426509608046373
• 作为产物：
  描述：

  D-threo-[2]pentosulose-bis-phenylhydrazone 在 copper(II) sulfate 作用下， 以 水 为溶剂， 生成 2-phenyl-4-(D-threo-1',2',3'-trihydroxypropyl)-2H-1,2,3-triazole
  参考文献：
  名称：

  三唑基蔗糖的高效选择性生物催化酰化研究

  摘要：

  已经使用了不同的酸酐（C 2至C 7脂族脂肪酸和苯甲酸）来研究2-苯基-4-（d-苏式-1'，2'，3）中伯/仲羟基的选择性酰化'-三羟丙基）-2 H -1,2,3-三唑，2-苯基-4-（d-赤型-1'，2'，3'-三羟丙基）-2 H -1,2,3-三唑， 2-苯基-4-（d-阿拉伯糖-1'，2'，3'，4'-四羟基丁基）-2 H -1,2,3-三唑和2-苯基-4-（d- lyxo -1' ，2'，3'，4'-四羟基丁基）-2 H -1,2,3-三唑在南极假丝酵母的存在下二异丙醚中的脂肪酶B。在不同的酸酐中，丁酸酐被发现是最有效的酰化剂（用于丁酰化）。对于乙酰化，乙酸乙烯酯效果最好。与这两种酰化剂的反应具有很高的选择性和效率，在1–5小时内仅以95–99％的收率仅生成单酰化产物。

  DOI：

  10.1016/j.tet.2003.10.059

文献信息

• The Action of Copper Sulfate on the Phenyl Osazones of the Sugars. II. Some New Osotriazoles
  作者：W. T. Haskins、Raymond M. Hann、C. S. Hudson

  DOI：10.1021/ja01222a018

  日期：1945.6
• Novel Lipase-Catalysed Highly Selective Acetylation Studies on d-Arabino- and d-Threo-polyhydroxyalkyltriazoles
  作者：Ashok K Prasad、H. Himanshu、Anupam Bhattacharya、Carl E Olsen、Virinder S Parmar

  DOI：10.1016/s0968-0896(01)00350-9

  日期：2002.4

  Five 2-phenyl-4-(D-arabino-4'-cycloamino-3-hydroxy-O-1',2'-isopropylidene-butyl)-2H-1,2,3-triazoles. acyclonucleosides containing unnatural bases have been synthesised by opening of the epoxide ring of 2-phenyl-4-(D-arabino-3',4'-epoxy-O-1',2'-isopropylidenebutyl)-2H-1,2.3-triazole with the corresponding cyclic amines in 70-85% yields. The starting arabino-epoxytriazole was prepared in five steps starting from D-glucose in an overall yield of 15%. All the five triazolylacyclonucleosides were unambiguously identified on the basis of their spectral data. The Structure of one of the intermediates. that is 2-phenyl-4-(D-arabino-1',2',3',4'-tetrahydroxybutyl)-2H-1,2.3-triazole was confirmed by its X-ray crystallographic studies. These acyclonucleosides were subjected to antiviral activity evaluation in CEM-SS cell-based anti HIV assay with the lymphocytropic virus strains HIV-1(IIIB) and HIV-1(RF). (C) 2002 Elsevier Science Ltd. All rights reserved.