ethyl 5-[(1S)-1-hydroxyethyl]-2-methylfuran-3-carboxylate | 1043017-62-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: ethyl 5-[(1S)-1-hydroxyethyl]-2-methylfuran-3-carboxylate
• CAS: 1043017-62-4
• 化学式: C₁₀H₁₄O₄
• 分子量: 198.219
• InChiKey: QOHPVQJGDBRWSD-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2-萘甲酰基)咪唑 、 ethyl 5-[(1S)-1-hydroxyethyl]-2-methylfuran-3-carboxylate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 ethyl 2-methyl-5-[(1S)-1-(naphthalene-2-carbonyloxy)ethyl]furan-3-carboxylate
  参考文献：
  名称：

  The configurational assignment of the optically active 5-(1-hydro-peoxyethyl)-3-ethoxycarbonyl-2-methylfuran and its alcohol by exciton-coupled circular dichroism (ECCD)

  摘要：

  The absolute configuration of the furan-derived hydroperoxide land its alcohol 2, readily available in optically active form by kinetic resolution of the racemic hydroperoxide with horseradish peroxidase (HRP), was determined by the exciton-coupled circular dichroism (ECCD) method on their 2-naphthoate derivatives 4. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00515-6
• 作为产物：
  描述：

  5-(1-hydroperoxyethyl)-3-ethoxycarbonyl-2-methylfuran 在 三苯基膦 作用下， 生成 ethyl 5-[(1S)-1-hydroxyethyl]-2-methylfuran-3-carboxylate
  参考文献：
  名称：

  The configurational assignment of the optically active 5-(1-hydro-peoxyethyl)-3-ethoxycarbonyl-2-methylfuran and its alcohol by exciton-coupled circular dichroism (ECCD)

  摘要：

  The absolute configuration of the furan-derived hydroperoxide land its alcohol 2, readily available in optically active form by kinetic resolution of the racemic hydroperoxide with horseradish peroxidase (HRP), was determined by the exciton-coupled circular dichroism (ECCD) method on their 2-naphthoate derivatives 4. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00515-6

文献信息

• Asymmetric Synthesis with the Enzyme <i>Coprinus</i> Peroxidase:  Kinetic Resolution of Chiral Hydroperoxides and Enantioselective Sulfoxidation
  作者：Waldemar Adam、Cordula Mock-Knoblauch、Chantu R. Saha-Möller

  DOI：10.1021/jo990201p

  日期：1999.6.1

  hydroperoxide 1a afforded with CiP enantiomerically enriched hydroperoxide 1a (ee up to 54%) and alcohol 2a (ee up to 40%), as well as ketone 3a (which is also formed simultaneously in all other reactions) and molecular oxygen. Catalase activity was established for CiP with hydrogen peroxide. When aryl alkyl sulfides 4 were used as oxygen acceptors, three products, sulfoxides 5, alcohols 2, and hydroperoxides

  Coprinus过氧化物酶（CiP）用于外消旋氢过氧化物1的动力学拆分和前手性硫化物4的不对称硫氧化。在动力学分辨率的条件下，CiP和愈创木酚作为还原剂还原了11种氢过氧化物1a-k，对映选择性最高> （S）-氢过氧化物1的98％和（R）-醇2的90％。在没有还原剂的情况下，氢过氧化物1a提供了CiP对映异构体富集的氢过氧化物1a（ee最高为54％）和醇2a（ ee高达40％），酮3a（在所有其他反应中也同时形成）和分子氧。用过氧化氢确定了CiP的过氧化氢酶活性。将芳基烷基硫化物4用作氧受体时，得到三种产物：亚砜5，醇2和氢过氧化物1，全部以对映体富集的形式存在。衍生自萘基甲基硫化物（4f）的亚砜的最高ee值（89％）。因此，CiP可用于光学活性氢过氧化物1，醇2和亚砜5的不对称合成。
• The configurational assignment of the optically active 5-(1-hydro-peoxyethyl)-3-ethoxycarbonyl-2-methylfuran and its alcohol by exciton-coupled circular dichroism (ECCD)
  作者：Waldemar Adam、Hans-Ulrich Humpf、Marion N. Korb、Peter Schreier

  DOI：10.1016/s0957-4166(97)00515-6

  日期：1997.11

  The absolute configuration of the furan-derived hydroperoxide land its alcohol 2, readily available in optically active form by kinetic resolution of the racemic hydroperoxide with horseradish peroxidase (HRP), was determined by the exciton-coupled circular dichroism (ECCD) method on their 2-naphthoate derivatives 4. (C) 1997 Elsevier Science Ltd.