3-(M-甲氧基苯氧基)-1,2-丙烷二醇 | 17131-51-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 3-(M-甲氧基苯氧基)-1,2-丙烷二醇
• 英文名称: 3-(3-methoxyphenoxy)-1,2-propanediol
• 英文别名: 3-(3-methoxy-phenoxy)-propane-1,2-diol；3-(3-Methoxy-phenoxy)-propan-1,2-diol；3-(3-Methoxy-phenoxy)-propandiol-(1,2)；Glycerin-1-(3-methoxyphenyl)ether；Miocain；3-(3-Methoxyphenoxy)propane-1,2-diol
• CAS: 17131-51-0
• 化学式: C₁₀H₁₄O₄
• 分子量: 198.219
• InChiKey: PVXJBKOQPCPILX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2909499000

反应信息

• 作为反应物：
  描述：

  3-(M-甲氧基苯氧基)-1,2-丙烷二醇 在 ion-exchange resin Wofatit SBW (OH(-)-form) 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 100.0h， 生成 (2S)-3-(3-methoxyphenoxy)propane-1,2-diol
  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：

  3-甲氧基苯酚 在 sodium hydroxide 、 高氯酸 作用下， 以 水 为溶剂， 反应 4.0h， 生成 3-(M-甲氧基苯氧基)-1,2-丙烷二醇
  参考文献：
  名称：

  Crown cation complex effects. 20. Syntheses and cation binding properties of carbon-pivot lariat ethers

  摘要：

  DOI：

  10.1021/ja00341a045

文献信息

• Ueda,T. et al., Chemical and pharmaceutical bulletin, 1960, vol. 8, p. 921 - 929
  作者：Ueda,T. et al.

  DOI：——

  日期：——
• Muscle-Relaxing Compounds Similar to 3-(o-Toloxy)-1,2-propanediol. II. Substituted Alkanediols¹
  作者：Harry L. Yale、Edward J. Pribyl、William Braker、Jack Bernstein、W. A. Lott

  DOI：10.1021/ja01164a108

  日期：1950.8
• Mazurkiewicz; Supniewski, Dissertationes Pharmaceuticae, 1950, vol. 2, p. 191,194, 195
  作者：Mazurkiewicz、Supniewski

  DOI：——

  日期：——
• Kinetic resolution of aliphatic 1,2-diols by a lipase-catalyzed sequential acetylation
  作者：Fritz Theil、Judith Weidner、Sibylle Ballschuh、Annamarie Kunath、Hans Schick

  DOI：10.1016/s0040-4039(00)60573-7

  日期：1993.1

  The kinetic resolution of 13 racemic aliphatic 1,2-diols (rac-1a-m) by means of a lipase-catalyzed sequential acetylation was investigated. The enantioselectivity of the 3-aryloxy-propane-1,2-diols rac-1a-k depends on the substitution pattern at the aryl ring.
• 5-Aryloxymethyl-2-oxazolidinones
  作者：Carl D. Lunsford、Richard P. Mays、John A. Richman、Robert S. Murphey

  DOI：10.1021/ja01490a037

  日期：1960.3