2-azido-2-(2,2-dimethyl[1,3]dioxolan-4-yl)ethanol | 1010701-88-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-azido-2-(2,2-dimethyl[1,3]dioxolan-4-yl)ethanol
• 英文别名: 3-azido-1,2-O-isopropylidene-3-deoxy-D-erythritol；(2R)-2-azido-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol
• CAS: 1010701-88-8
• 化学式: C₇H₁₃N₃O₃
• 分子量: 187.199
• InChiKey: NJBYIXHQMYUHRG-RITPCOANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  53
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-azido-2-(2,2-dimethyl[1,3]dioxolan-4-yl)ethanol 在 吡啶 、 potassium carbonate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 1-azido-1-(2,2-dimethyl[1,3]dioxolan-4-yl)-2-(4-phenylpiperazine-perazine-1-yl)ethane
  参考文献：
  名称：

  Synthesis and Stereospecificity of 4,5-Disubstituted Oxazolidinone Ligands Binding to T-box Riboswitch RNA

  摘要：

  The enantiomers and the cis isomers of two previously studied 4,5-disubstituted oxazolidinones have been synthesized, and their binding to the T-box riboswitch antiterminator model RNA has been investigated in detail. Characterization of ligand affinities and binding site localization indicates that there is little stereospecific discrimination for binding antiterminator RNA alone. This binding similarity between enantiomers is likely due to surface binding, which accommodates ligand conformations 1 that result in comparable ligand-antiterminator contacts. These results have significant implications for T-box antiterminator-targeted drug discovery and, in general, for targeting other medicinally relevant RNA that do not present deep binding pockets.

  DOI：

  10.1021/jm2006904
• 作为产物：
  描述：

  在 4-甲基苯磺酸吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以100%的产率得到2-azido-2-(2,2-dimethyl[1,3]dioxolan-4-yl)ethanol
  参考文献：
  名称：

  脯氨酸催化的醛醇缩合反应的双重不对称诱导的起源。

  摘要：

  已经使用HF / 6-31G（d）计算进行了计算研究，以阐明脯氨酸催化的羟醛反应的双重不对称诱导的起源。计算的过渡结构解释了获得的实验数据。

  DOI：

  10.1021/jo800934b

文献信息

• Efficient nucleophilic oxirane ring cleavage with dibutyltin diazide
  作者：Seiki Saito、Toshiya Nishikawa、Yoshie Yokoyama、Toshio Moriwake

  DOI：10.1016/s0040-4039(00)94376-4

  日期：1990.1

  Dibutyltin diazide has proven to be potential in nucleophilic ring opening of a variety of oxiranes to give 1,2-azido alcohols in less than four hours (DMF at 60 °C) in fair to excellent yields.

  二叠氮化二丁基锡已被证明可能在多种环氧乙烷的亲核开环中以不到四小时的时间（在60°C的DMF条件下）产生1,2-叠氮基醇，并且具有相当高的收率。
• Synthesis and Stereospecificity of 4,5-Disubstituted Oxazolidinone Ligands Binding to T-box Riboswitch RNA
  作者：Crina M. Orac、Shu Zhou、John A. Means、David Boehm、Stephen C. Bergmeier、Jennifer V. Hines

  DOI：10.1021/jm2006904

  日期：2011.10.13

  The enantiomers and the cis isomers of two previously studied 4,5-disubstituted oxazolidinones have been synthesized, and their binding to the T-box riboswitch antiterminator model RNA has been investigated in detail. Characterization of ligand affinities and binding site localization indicates that there is little stereospecific discrimination for binding antiterminator RNA alone. This binding similarity between enantiomers is likely due to surface binding, which accommodates ligand conformations 1 that result in comparable ligand-antiterminator contacts. These results have significant implications for T-box antiterminator-targeted drug discovery and, in general, for targeting other medicinally relevant RNA that do not present deep binding pockets.
• Origins of the Double Asymmetric Induction on Proline-Catalyzed Aldol Reactions
  作者：Félix Calderón、Elisa G. Doyagüez、Paul Ha-Yeon Cheong、Alfonso Fernández-Mayoralas、K. N. Houk

  DOI：10.1021/jo800934b

  日期：2008.10.17

  Computational studies to elucidate the origin of the double asymmetric induction on proline-catalyzed aldol reaction have been performed using HF/6-31G(d) calculations. The computed transition structures explain the experimental data obtained.

  已经使用HF / 6-31G（d）计算进行了计算研究，以阐明脯氨酸催化的羟醛反应的双重不对称诱导的起源。计算的过渡结构解释了获得的实验数据。