(4R)-1,2-O-isopropylidene-3-O-benzyl-4-C-[(1-(2-nitrophenyl)-1H-1,2,3-triazol-4-yl)]-L-threofuranose | 1160926-69-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (4R)-1,2-O-isopropylidene-3-O-benzyl-4-C-[(1-(2-nitrophenyl)-1H-1,2,3-triazol-4-yl)]-L-threofuranose
• 英文别名: 4-[(3aR,5R,6S,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-1-(2-nitrophenyl)triazole
• CAS: 1160926-69-1
• 化学式: C₂₂H₂₂N₄O₆
• 分子量: 438.44
• InChiKey: OBZLHCAKHMEDFH-PLACYPQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-ynofuranose 、 1-氟-2-硝基苯 在 sodium azide 、 copper(ll) sulfate pentahydrate 、 sodium carbonate 、 sodium ascorbate 、 L-脯氨酸 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 24.0h， 以71%的产率得到(4R)-1,2-O-isopropylidene-3-O-benzyl-4-C-[(1-(2-nitrophenyl)-1H-1,2,3-triazol-4-yl)]-L-threofuranose
  参考文献：
  名称：

  A Cu(I)-promoted one-pot ‘SNAr–click reaction’ of fluoronitrobenzenes

  摘要：

  A one-pot two-step sequence involving a nucleophilic aromatic substitution (SNAF) of activated fluorobenzenes with azide nucleophile and in situ Huisgen cycloaddition of the resulting aryl azides with alkynes has been developed for a rapid access to 1,4-substituted triazoles. Control experiments revealed that both the steps are catalyzed by Cu(I) and also the course of reaction as SNAr followed by [3+2]-cycloaddition. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.03.035

文献信息

• A Cu(I)-promoted one-pot ‘SNAr–click reaction’ of fluoronitrobenzenes
  作者：Kulbhushan A. Dururgkar、Rajesh G. Gonnade、C.V. Ramana

  DOI：10.1016/j.tet.2009.03.035

  日期：2009.5

  A one-pot two-step sequence involving a nucleophilic aromatic substitution (SNAF) of activated fluorobenzenes with azide nucleophile and in situ Huisgen cycloaddition of the resulting aryl azides with alkynes has been developed for a rapid access to 1,4-substituted triazoles. Control experiments revealed that both the steps are catalyzed by Cu(I) and also the course of reaction as SNAr followed by [3+2]-cycloaddition. (C) 2009 Elsevier Ltd. All rights reserved.