2-tosylethyl 3-hydroxy-2,2-bis(hydroxymethyl)propanoate | 1309460-01-2

• 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-tosylethyl 3-hydroxy-2,2-bis(hydroxymethyl)propanoate
• CAS: 1309460-01-2
• 化学式: C₁₄H₂₀O₇S
• 分子量: 332.375
• InChiKey: QLAVLVPPSXQBIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.72
• 重原子数：
  22.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  121.13
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  cis-5-methyl-2-phenyl-1,3-dioxane-5-carboxylic anhydride 、 2-tosylethyl 3-hydroxy-2,2-bis(hydroxymethyl)propanoate 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 以93%的产率得到2-(toluenesulfonyl)ethyl bis-2,2-(5-methyl-2-phenyl-1,3-dioxane-5-carbonyloxy)methyl-3-(5-methyl-2-phenyl-1,3-dioxane-5-carbonyloxy)propanoate
  参考文献：
  名称：

  Efficient and Controllably Selective Preparation of Esters Using Uronium-Based Coupling Agents

  摘要：

  Carboxylic acid esters can be prepared in excellent yields at room temperature from an acid and either a phenol or an aliphatic alcohol using Me peptide coupling reagents, TBTU, TATU, or COMU, in the presence of organic bases. Reactions using TBTU and TATU are faster but do not occur with tertiary alcohols. Selectivity between reaction with primary or secondary alcohols in diols and polyols can be achieved with choice of base and coupling agent.

  DOI：

  10.1021/ol201005s
• 作为产物：
  描述：

  3-(benzyloxy)-2,2-bis(benzyloxymethyl)propanoic anhydride 在 吡啶 、 4-二甲氨基吡啶 、 palladium on carbon 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 2-tosylethyl 3-hydroxy-2,2-bis(hydroxymethyl)propanoate
  参考文献：
  名称：

  Efficient and Controllably Selective Preparation of Esters Using Uronium-Based Coupling Agents

  摘要：

  Carboxylic acid esters can be prepared in excellent yields at room temperature from an acid and either a phenol or an aliphatic alcohol using Me peptide coupling reagents, TBTU, TATU, or COMU, in the presence of organic bases. Reactions using TBTU and TATU are faster but do not occur with tertiary alcohols. Selectivity between reaction with primary or secondary alcohols in diols and polyols can be achieved with choice of base and coupling agent.

  DOI：

  10.1021/ol201005s