(RS)-3-(2-methoxyphenoxy)-propane-1,2-diyl diacetate | 92865-65-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (RS)-3-(2-methoxyphenoxy)-propane-1,2-diyl diacetate
• 英文别名: 1,2-di-O-acetyl-3-(2-methoxyphenoxy)propane-1,2-diol；2,3-Di-O-acetyl-1-O-(2-methoxy-phenyl)-glycerin；1,2-Diacetoxy-3-(2-methoxyphenoxy)propane；[2-acetyloxy-3-(2-methoxyphenoxy)propyl] acetate
• CAS: 92865-65-1
• 化学式: C₁₄H₁₈O₆
• 分子量: 282.293
• InChiKey: HPQAMKIXSOVULB-UHFFFAOYSA-N

物化性质

• 保留指数：
  1865

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (RS)-3-(2-methoxyphenoxy)-propane-1,2-diyl diacetate 在 ion-exchange resin Wofatit SBW (OH(-)-form) 作用下， 以 甲醇 为溶剂， 生成 (R)-guaifenesin 、 (S)-guaifenesin
  参考文献：
  名称：

  Kinetic resolution of acyclic 1,2-diols using a sequential lipase-catalyzed transesterification in organic solvents

  摘要：

  A method for the kinetic resolution of 3-(aryloxy)-1,2-propanediols rac-1a-n without additional protection-deprotection steps using a lipase-catalyzed sequential transesterification with lipase amnno PS has been developed. In the first step of this one-pot procedure the racemic 1,2-diols are acylated regioselectively at the primary hydroxy group without enantioselection. The subsequent acylation at the secondary hydroxy group of the formed primary monoacetate is responsible for high enantioselection. The enantioselectivity of this transformation depends significantly on the substitution pattern of the aryl ring and the organic solvent used. 3-(Aryloxy)-1,2-propanediols with substituents in the para-position show a much higher enantioselectivity than the corresponding derivatives with ortho-substituents. Among other substrates, the pharmaceuticals Mephenesin, Guaifenesin, and Chlorphenesin have been resolved. The replacement of the aryloxy by alkyl substituent causes a dramatic decrease of enantioselectivity.

  DOI：

  10.1021/jo00081a018
• 作为产物：
  描述：

  木榴油 在 吡啶 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 16.0h， 生成 (RS)-3-(2-methoxyphenoxy)-propane-1,2-diyl diacetate
  参考文献：
  名称：

  化学酶途径合成潜在的β-阻滞剂（S）-Moprolol

  摘要：

  此处报道了潜在的β-受体阻滞剂（S）-莫普洛尔合成的生物催化途径。莫泊洛尔的对映纯合成主要取决于手性中间体3-（2-（2-甲氧基苯氧基）-丙烷-1,2-二醇）。筛选了各种商品化脂肪酶以筛选（RS）-3-（2-甲氧基苯氧基）丙烷-1,2-二醇的对映选择性，以产生所需的对映异构体。其中，黑曲霉脂肪酶（ANL）的选择基于立体选择性和区域选择性。确定了各种反应参数的最佳值，例如酶（15 mg / mL），底物浓度（10 mM），有机溶剂（甲苯），反应温度（30°C）和时间（18 h）。导致对映体过量的（S）-3-（2-甲氧基苯氧基）丙烷-1,2-二醇的收率超过49％。脂肪酶介导的催化显示区域选择性酰化和双重立体选择性。此外，对映体纯中间体用于合成（S）-moprolol，可提供所需的β-受体阻滞剂。手性28：313–318，2016。©2016 Wiley Periodicals，Inc.

  DOI：

  10.1002/chir.22574

文献信息

• Discriminative Glycosylation of 3-(Aryloxy)propane-1,2-diols by Choice of a Glycosyl Donor
  作者：Hari Babu Mereyala、Sreeman Kumar Mamidyala、Krishna Prasad Chigurupati、Sastri R. Srinivasa

  DOI：10.1055/s-2003-42437

  日期：——

  Regioselective glycosylation of rac-guaifenesin (1A) with various glycosyl donors viz., β-d -glucosepentaacetate (2), pyridyl 2,3,4,6-O-tetra-O-benzyl-1-thio-β-d-galactopyranoside (9), 1-O-acetyl-2,3,5-tri-O-benzoyl-α/β-d-ribo- (13) and xylofuranoside (17) is reported. Glycosyl donors 2, 13 and 17 bearing ester protecting groups is reported to exhibit high regioselectivity to form the corresponding diastereomeric mixture of 1-O-glycosylated guaifenesin derivatives 3A, 14A and 18A, respectively; formation of diglycosylated derivatives 5A, 15A and 19A is not observed. While no such selectivity is observed when the donor 9 bearing ether protecting groups is used in the coupling reaction with 1A, resulting in the formation of digalactosylated derivatives 10A. That the regioselectivity is not dependent upon substituents present on the aromatic ring is shown by coupling 1B with 2 to isolate 1-O-glycosylated derivative 3B; formation of diglycosylated derivative 5B was not observed. Applicability of this finding is shown by preparation of enantiopure guaifenesin [(R)-1 (98% ee) and (S)-1 (98% ee)] by separation of their corresponding diastereomers (R)-3 and (S)- 3, respectively.

  本文报道了消旋的愈创甘油醚（1A）与各种糖供体，即β-D-葡萄糖五乙酸酯（2）、吡啶基2,3,4,6-O-四苄基-1-硫代-β-D-半乳糖吡喃糖苷（9）、1-O-乙酰基-2,3,5-三-O-苯甲酰基-α/β-D-核糖-（13）和木糖呋喃糖苷（17）的区域选择性糖基化反应。具有酯保护基的糖供体2、13和17被报道表现出高度的区域选择性，分别形成相应的1-O-糖基化愈创甘油醚衍生物3A、14A和18A的非对映异构体混合物；未观察到形成二糖基化衍生物5A、15A和19A。然而，当使用具有醚保护基的供体9进行与1A的偶联反应时，未观察到这种选择性，导致形成了二半乳糖基化衍生物10A。通过将1B与2偶联并分离出1-O-糖基化衍生物3B，表明区域选择性不依赖于芳环上的取代基；未观察到形成二糖基化衍生物5B。这一发现的适用性通过分离其相应的非对映异构体（R）-3和（S）-3，分别制备了具有高对映体纯度的愈创甘油醚[(R)-1（98% ee）和(S)-1（98% ee）]。
• Chemoenzymatic Route for the Synthesis of (<i>S</i> )-Moprolol, a Potential β-Blocker
  作者：Saptarshi Ghosh、Jayeeta Bhaumik、Linga Banoth、Sooram Banesh、Uttam Chand Banerjee

  DOI：10.1002/chir.22574

  日期：2016.4

  A biocatalytic route for the synthesis of a potential β‐blocker, (S)‐moprolol is reported here. Enantiopure synthesis of moprolol is mainly dependent on the chiral intermediate, 3‐(2‐methoxyphenoxy)‐propane‐1,2‐diol. Various commercial lipases were screened for the enantioselective resolution of (RS)‐3‐(2‐methoxyphenoxy)propane‐1,2‐diol to produce the desired enantiomer. Among them, Aspergillus niger

  此处报道了潜在的β-受体阻滞剂（S）-莫普洛尔合成的生物催化途径。莫泊洛尔的对映纯合成主要取决于手性中间体3-（2-（2-甲氧基苯氧基）-丙烷-1,2-二醇）。筛选了各种商品化脂肪酶以筛选（RS）-3-（2-甲氧基苯氧基）丙烷-1,2-二醇的对映选择性，以产生所需的对映异构体。其中，黑曲霉脂肪酶（ANL）的选择基于立体选择性和区域选择性。确定了各种反应参数的最佳值，例如酶（15 mg / mL），底物浓度（10 mM），有机溶剂（甲苯），反应温度（30°C）和时间（18 h）。导致对映体过量的（S）-3-（2-甲氧基苯氧基）丙烷-1,2-二醇的收率超过49％。脂肪酶介导的催化显示区域选择性酰化和双重立体选择性。此外，对映体纯中间体用于合成（S）-moprolol，可提供所需的β-受体阻滞剂。手性28：313–318，2016。©2016 Wiley Periodicals，Inc.
• Kinetic resolution of acyclic 1,2-diols using a sequential lipase-catalyzed transesterification in organic solvents
  作者：Fritz Theil、Judith Weidner、Sibylle Ballschuh、Annamarie Kunath、Hans Schick

  DOI：10.1021/jo00081a018

  日期：1994.1

  A method for the kinetic resolution of 3-(aryloxy)-1,2-propanediols rac-1a-n without additional protection-deprotection steps using a lipase-catalyzed sequential transesterification with lipase amnno PS has been developed. In the first step of this one-pot procedure the racemic 1,2-diols are acylated regioselectively at the primary hydroxy group without enantioselection. The subsequent acylation at the secondary hydroxy group of the formed primary monoacetate is responsible for high enantioselection. The enantioselectivity of this transformation depends significantly on the substitution pattern of the aryl ring and the organic solvent used. 3-(Aryloxy)-1,2-propanediols with substituents in the para-position show a much higher enantioselectivity than the corresponding derivatives with ortho-substituents. Among other substrates, the pharmaceuticals Mephenesin, Guaifenesin, and Chlorphenesin have been resolved. The replacement of the aryloxy by alkyl substituent causes a dramatic decrease of enantioselectivity.