4-(benzyloxy)butan-2-yl methyl carbonate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(benzyloxy)butan-2-yl methyl carbonate
• 英文别名: methyl 4-phenylmethoxybutan-2-yl carbonate
• 化学式: C₁₃H₁₈O₄
• 分子量: 238.284
• InChiKey: ACRXFWRMLLIOGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.76
• 重原子数：
  17.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  4-benzyloxy-2-butanol 、 氯甲酸甲酯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以86%的产率得到4-(benzyloxy)butan-2-yl methyl carbonate
  参考文献：
  名称：

  Kinetic resolution of poly(ethylene glycol)-supported carbonates by enzymatic hydrolysis

  摘要：

  The enzyme-mediated enantioselective hydrolysis of poly(ethylene glycol) (PEG)-supported carbonates is disclosed. The water-soluble carbonates were prepared by immobilization of a racemic secondary alcohol (4-benzyloxy-2-butanol) onto low-molecular weight (av MW 550 and 750) monometboxy PEG through a carbonate linker. For the screening of the hydrolytic enzymes, the substrate was enantioselectively hydrolyzed by commercially available lipase from porcine pancreas (PPL; Type II, Sigma) to afford the optically active compounds. In this system, the separation of the remaining (S)-substrate and the resulting (R)-alcohol was achieved by an extraction process without a laborious column chromatography. The (S)-carbonate was easily hydrolyzed with K2CO3 to afford the corresponding (S)-alcohol. Other MPEG-supported substrates were also hydrolyzed to afford the corresponding optically active alcohols. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.05.020

文献信息

• Kinetic resolution of poly(ethylene glycol)-supported carbonates by enzymatic hydrolysis
  作者：Masaki Nogawa、Megumi Shimojo、Kazutsugu Matsumoto、Masayuki Okudomi、Yuji Nemoto、Hiromichi Ohta

  DOI：10.1016/j.tet.2006.05.020

  日期：2006.7

  The enzyme-mediated enantioselective hydrolysis of poly(ethylene glycol) (PEG)-supported carbonates is disclosed. The water-soluble carbonates were prepared by immobilization of a racemic secondary alcohol (4-benzyloxy-2-butanol) onto low-molecular weight (av MW 550 and 750) monometboxy PEG through a carbonate linker. For the screening of the hydrolytic enzymes, the substrate was enantioselectively hydrolyzed by commercially available lipase from porcine pancreas (PPL; Type II, Sigma) to afford the optically active compounds. In this system, the separation of the remaining (S)-substrate and the resulting (R)-alcohol was achieved by an extraction process without a laborious column chromatography. The (S)-carbonate was easily hydrolyzed with K2CO3 to afford the corresponding (S)-alcohol. Other MPEG-supported substrates were also hydrolyzed to afford the corresponding optically active alcohols. (c) 2006 Elsevier Ltd. All rights reserved.