3-(4-methylphenoxyl)-1,2-diacetoxy-propane | 58888-41-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(4-methylphenoxyl)-1,2-diacetoxy-propane
• 英文别名: 3-(p-Tolyloxy)-propylendiacetat；[2-Acetyloxy-3-(4-methylphenoxy)propyl] acetate
• CAS: 58888-41-8
• 化学式: C₁₄H₁₈O₅
• 分子量: 266.294
• InChiKey: UJVVUMDDBJJYNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(4-methylphenoxyl)-1,2-diacetoxy-propane 在 ion-exchange resin Wofatit SBW (OH(-)-form) 作用下， 以 甲醇 为溶剂， 生成 (R)-3-(4-methylphenoxy)-propane-1,2-diol 、 (S)-3-(4-methylphenoxy)-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：

  对叔丁基苯基1-(2,3-环氧)丙基醚 、 乙酸酐 在 zeolite HY 作用下， 反应 14.0h， 以90%的产率得到3-(4-methylphenoxyl)-1,2-diacetoxy-propane
  参考文献：
  名称：

  沸石催化环氧化物与乙酸酐的开环开环*

  摘要：

  发现 HY 沸石是一种通用催化剂，用于将环氧化物以良好的收率与乙酸酐开环成相应的乙酰化 1,2-二醇。*IICT 通讯第 4521 号。

  DOI：

  10.1081/scc-100105384

文献信息

• 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.
• ZEOLITE CATALYZED RING OPENING OF EPOXIDES TO ACETYLATED DIOLS WITH ACETIC ANHYDRIDE^*
  作者：P. Ramesh、V. L. Niranjan Reddy、D. Venugopal、M. Subrahmanyam、Y. Venkateswarlu

  DOI：10.1081/scc-100105384

  日期：2001.1.1

  HY Zeolite is found to be a versatile catalyst for opening of epoxides to the corresponding acetylated 1,2-Diols with acetic anhydride in good yields. *IICT Communication No. 4521.

  发现 HY 沸石是一种通用催化剂，用于将环氧化物以良好的收率与乙酸酐开环成相应的乙酰化 1,2-二醇。*IICT 通讯第 4521 号。