α,α'-dimethyl-2,6-pyridinedimethanol diacetate | 143329-87-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: α,α'-dimethyl-2,6-pyridinedimethanol diacetate
• 英文别名: 2,6-bis(1-acetoxyethyl)pyridine；1-[6-(1-acetyloxyethyl)pyridin-2-yl]ethyl acetate
• CAS: 143329-87-7
• 化学式: C₁₃H₁₇NO₄
• 分子量: 251.282
• InChiKey: BLSKALQIQQLILA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.33
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  65.49
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  α,α'-dimethyl-2,6-pyridinedimethanol diacetate 在 Novozym 435 lipase 作用下， 以 phosphate buffer 为溶剂， 反应 48.0h， 以18%的产率得到(R,R)-α,α'-dimethyl-2,6-pyridinedimethanol
  参考文献：
  名称：

  化学酶法制备2-（1-羟乙基）-和2,6-双（1-羟乙基）吡啶及其乙酸酯的所有立体异构体

  摘要：

  几个脂肪酶中测试的外消旋-吡啶-2-基-6-（1-羟乙基）]乙酮对映异构选择性乙酰化1-外消旋- 2，得到醇（小号） - 2和乙酸（[R ） - 3。外消旋和内消旋-2,6-双（1-羟基-乙基）吡啶的非对映异构体混合物rac / meso - 4与乙酸乙烯酯中选择性最高的Novozym 435脂肪酶的乙酰化反应产生对映体纯二醇（S，小号） - 4，单乙酸酯（- [R ，小号） - 5和二乙酸盐（ř，R）-6。外消旋和内消旋-2,6-双（1-乙酰氧基乙基）吡啶rac / meso - 6的混合物通过相同的酶水解，得到二醇（R，R）-4，单乙酸（S，R）-的纯对映体5和二乙酸（S，S）-6。使用其他化学和酶促步骤，醇（R）-2，乙酸酯（S）-3，（S，S）-和（R，[R）-monoacetates（小号，小号） - 5和（- [R ，- [R ）- 5，内消旋- 4及其乙酸酯内消旋- 6还制备和表征。

  DOI：

  10.1016/j.tetasy.2004.07.004
• 作为产物：
  描述：

  2,6-二乙酰基吡啶 在 sodium tetrahydroborate 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 α,α'-dimethyl-2,6-pyridinedimethanol diacetate
  参考文献：
  名称：

  化学酶法制备2-（1-羟乙基）-和2,6-双（1-羟乙基）吡啶及其乙酸酯的所有立体异构体

  摘要：

  几个脂肪酶中测试的外消旋-吡啶-2-基-6-（1-羟乙基）]乙酮对映异构选择性乙酰化1-外消旋- 2，得到醇（小号） - 2和乙酸（[R ） - 3。外消旋和内消旋-2,6-双（1-羟基-乙基）吡啶的非对映异构体混合物rac / meso - 4与乙酸乙烯酯中选择性最高的Novozym 435脂肪酶的乙酰化反应产生对映体纯二醇（S，小号） - 4，单乙酸酯（- [R ，小号） - 5和二乙酸盐（ř，R）-6。外消旋和内消旋-2,6-双（1-乙酰氧基乙基）吡啶rac / meso - 6的混合物通过相同的酶水解，得到二醇（R，R）-4，单乙酸（S，R）-的纯对映体5和二乙酸（S，S）-6。使用其他化学和酶促步骤，醇（R）-2，乙酸酯（S）-3，（S，S）-和（R，[R）-monoacetates（小号，小号） - 5和（- [R ，- [R ）- 5，内消旋- 4及其乙酸酯内消旋- 6还制备和表征。

  DOI：

  10.1016/j.tetasy.2004.07.004

文献信息

• Separation of remote diol and triol stereoisomers by enzyme-catalyzed esterification in organic media or hydrolysis in aqueous media
  作者：J. Shield Wallace、Bruce W. Baldwin、Cary Morrow

  DOI：10.1021/jo00045a042

  日期：1992.9

  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.