α,α',α''-trimethyl-1,3,5-benzenetrimethanol triacetate | 111443-89-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: α,α',α''-trimethyl-1,3,5-benzenetrimethanol triacetate
• 英文别名: 1,3,5-tris-(1-acetoxy-ethyl)-benzene；1,3,5-Tris-(1-acetoxy-aethyl)-benzol；1-[3,5-bis(1-acetyloxyethyl)phenyl]ethyl acetate
• CAS: 111443-89-1；143394-18-7；148496-74-6
• 化学式: C₁₈H₂₄O₆
• 分子量: 336.385
• InChiKey: BYVHRDKUOKMJHZ-UHFFFAOYSA-N

物化性质

• 沸点：
  376.6±37.0 °C(Predicted)
• 密度：
  1.122±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.56
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  78.9
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  α,α',α''-trimethyl-1,3,5-benzenetrimethanol triacetate 在 sodium hydroxide 作用下， 以 甲醇 、 苯 为溶剂， 反应 672.0h， 生成 (R,R,S)-α,α',α''-trimethyl-1,3,5-benzenetrimethanol
  参考文献：
  名称：

  Separation of remote diol and triol stereoisomers by enzyme-catalyzed esterification in organic media or hydrolysis in aqueous media

  摘要：

  The separation of symmetric, remote, secondary diol stereoisomers by steroselective enzyme-catalyzed acetylation with acetic anhydride in anhydrous, low polarity organic solvents or by stereoselective enzyme-catalyzed hydrolysis of the corresponding peracetate in aqueous media is described. Whether or not an alcohol is acetylated or an acetate is hydrolyzed is determined solely by its own stereochemical arrangement and not by the stereochemistry at any other stereogenic center. Since the enzyme used, Amano P lipoprotein lipase from Pseudomonas species, acetylates secondary alcohol stereogenic centers of the (R)-configuration, an (R,R)-diol is converted to its diacetate, a meso-diol is converted to the monoacetate at its (R)-stereogenic center, and an (S,S)-diol is left unchanged. Similarly, when hydrolysis is used, (R)-stereogenic centers are hydrolyzed so that the (R,R)-stereoisomer is converted to the corresponding diol while the (S,S)-stereoisomer remains a diacetate. The resulting mixture is separated, and the remaining acetates are removed by hydrolysis to give diols and triols of high stereochemical purity. Diols successively separated by esterification include alpha,alpha-dimethyl-1,4-benzenedimethanol, 1, alpha,alpha'-dimethyl-1,3-benzenedimethanol, 4, alpha,alpha'-dimethyl-2,6-pyridinedimethanol, 5, and alpha,alpha-dimethyl-4,4-biphenylenedimethanol, 6. For two cases, alpha,alpha'-dimethyl-2,6-pyridinedimethanol, 5, and alpha,alpha',alpha''-trimethyl-1,3,5-benzenetrimethanol, 7, the separation was achieved using the hydrolysis procedure. The stereochemical purity of each of the separated diol stereoisomers was determined by evaluating the NMR spectrum of its bis-MTPA ester. In most cases, it was possible to establish both the stereochemical purity of the fraction and the amount of each contaminating stereoisomer that was present. The diol products are expected to be of value for preparing optically active polymers and optically active crown ethers.

  DOI：

  10.1021/jo00045a042
• 作为产物：
  描述：

  三乙酰基苯 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 三乙胺 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 反应 2.0h， 生成 α,α',α''-trimethyl-1,3,5-benzenetrimethanol triacetate
  参考文献：
  名称：

  Separation of remote diol and triol stereoisomers by enzyme-catalyzed esterification in organic media or hydrolysis in aqueous media

  摘要：

  The separation of symmetric, remote, secondary diol stereoisomers by steroselective enzyme-catalyzed acetylation with acetic anhydride in anhydrous, low polarity organic solvents or by stereoselective enzyme-catalyzed hydrolysis of the corresponding peracetate in aqueous media is described. Whether or not an alcohol is acetylated or an acetate is hydrolyzed is determined solely by its own stereochemical arrangement and not by the stereochemistry at any other stereogenic center. Since the enzyme used, Amano P lipoprotein lipase from Pseudomonas species, acetylates secondary alcohol stereogenic centers of the (R)-configuration, an (R,R)-diol is converted to its diacetate, a meso-diol is converted to the monoacetate at its (R)-stereogenic center, and an (S,S)-diol is left unchanged. Similarly, when hydrolysis is used, (R)-stereogenic centers are hydrolyzed so that the (R,R)-stereoisomer is converted to the corresponding diol while the (S,S)-stereoisomer remains a diacetate. The resulting mixture is separated, and the remaining acetates are removed by hydrolysis to give diols and triols of high stereochemical purity. Diols successively separated by esterification include alpha,alpha-dimethyl-1,4-benzenedimethanol, 1, alpha,alpha'-dimethyl-1,3-benzenedimethanol, 4, alpha,alpha'-dimethyl-2,6-pyridinedimethanol, 5, and alpha,alpha-dimethyl-4,4-biphenylenedimethanol, 6. For two cases, alpha,alpha'-dimethyl-2,6-pyridinedimethanol, 5, and alpha,alpha',alpha''-trimethyl-1,3,5-benzenetrimethanol, 7, the separation was achieved using the hydrolysis procedure. The stereochemical purity of each of the separated diol stereoisomers was determined by evaluating the NMR spectrum of its bis-MTPA ester. In most cases, it was possible to establish both the stereochemical purity of the fraction and the amount of each contaminating stereoisomer that was present. The diol products are expected to be of value for preparing optically active polymers and optically active crown ethers.

  DOI：

  10.1021/jo00045a042