1,2-diacetoxy-3-(α-naphthyloxy)-propane | 253789-43-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,2-diacetoxy-3-(α-naphthyloxy)-propane
• 英文别名: (2-Acetyloxy-3-naphthalen-1-yloxypropyl) acetate
• CAS: 253789-43-4
• 化学式: C₁₇H₁₈O₅
• 分子量: 302.327
• InChiKey: FUSSNXRQRFNZPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  1,2-diacetoxy-3-(α-naphthyloxy)-propane 生成 (S)-1,2-diacetoxy-3-(α-naphthyloxy)-propane
  参考文献：
  名称：

  Resolution of 3-α-naphthoxy-1,2-propanediol using Candida antarctica lipase

  摘要：

  The stereochemistry of the Candida antarctica lipase B (CALB) catalyzed resolution of diacetate 1 or diol 4 was analyzed. The primary and secondary acetate hydrolyses were studied separately using monoacetates 2 and 3. The enantioselectivity of CALB was found to be lower towards primary rather than secondary acetates/alcohols. The steric course of the process is discussed. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00366-3
• 作为产物：
  描述：

  乙酸乙烯酯 、 3-(1-萘基氧基)-1,2-丙二醇 在 三乙胺 作用下， 以 various solvent(s) 为溶剂， 反应 124.0h， 生成 2-hydroxy-3-(α-naphthyloxy)-1-propyl acetate 、 Acetic acid (R)-2-hydroxy-3-(naphthalen-1-yloxy)-propyl ester 、 1,2-diacetoxy-3-(α-naphthyloxy)-propane
  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

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.
• Resolution of 3-α-naphthoxy-1,2-propanediol using Candida antarctica lipase
  作者：Loreto Salazar、Jose L. Bermudez、Cesar Ramı́rez、Emilio F. Llama、Jose V. Sinisterra

  DOI：10.1016/s0957-4166(99)00366-3

  日期：1999.9

  The stereochemistry of the Candida antarctica lipase B (CALB) catalyzed resolution of diacetate 1 or diol 4 was analyzed. The primary and secondary acetate hydrolyses were studied separately using monoacetates 2 and 3. The enantioselectivity of CALB was found to be lower towards primary rather than secondary acetates/alcohols. The steric course of the process is discussed. (C) 1999 Elsevier Science Ltd. All rights reserved.