4-(benzyloxy)butan-2-yl 1H-imidazole-1-carboxylate | 769961-67-3

• 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 1H-imidazole-1-carboxylate
• CAS: 769961-67-3
• 化学式: C₁₅H₁₈N₂O₃
• 分子量: 274.32
• InChiKey: JPMHGQHALKPBAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.86
• 重原子数：
  20.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  53.35
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  4-benzyloxy-2-butanol 、 N,N'-羰基二咪唑 以 二氯甲烷 为溶剂， 以100%的产率得到4-(benzyloxy)butan-2-yl 1H-imidazole-1-carboxylate
  参考文献：
  名称：

  Enzyme-mediated enantioselective hydrolysis of poly(ethylene glycol)-supported carbonates

  摘要：

  Kinetic resolution of poly(ethylene glycol)(PEG)-supported carbonates by enzymatic hydrolysis is discussed. Water-soluble carbonates are prepared by immobilization of racemic secondary alcohols onto low-molecular weight monomethoxy PEG (MPEG) through a carbonate linker. Porcine pancreas lipase (PPL) enantioselectively catalyzes the hydrolysis of the substrates to give optically active compounds. In this system, the separation of the resulting alcohols and the remaining substrates is achieved by an extraction process without laborious column chromatography. The carbonates are easily hydrolyzed with K2CO3 to afford the corresponding alcohols. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.07.031

文献信息

• Enzyme-mediated enantioselective hydrolysis of poly(ethylene glycol)-supported carbonates
  作者：Megumi Shimojo、Kazutsugu Matsumoto、Masaki Nogawa、Yuji Nemoto、Hiromochi Ohta

  DOI：10.1016/j.tetlet.2004.07.031

  日期：2004.8

  Kinetic resolution of poly(ethylene glycol)(PEG)-supported carbonates by enzymatic hydrolysis is discussed. Water-soluble carbonates are prepared by immobilization of racemic secondary alcohols onto low-molecular weight monomethoxy PEG (MPEG) through a carbonate linker. Porcine pancreas lipase (PPL) enantioselectively catalyzes the hydrolysis of the substrates to give optically active compounds. In this system, the separation of the resulting alcohols and the remaining substrates is achieved by an extraction process without laborious column chromatography. The carbonates are easily hydrolyzed with K2CO3 to afford the corresponding alcohols. (C) 2004 Elsevier Ltd. All rights reserved.
• 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.