rac-5-(1-ethoxyethoxy)-3-pentyn-2-ol | 171019-46-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: rac-5-(1-ethoxyethoxy)-3-pentyn-2-ol
• 英文别名: 5-(1-Ethoxyethoxy)pent-3-yn-2-ol；5-(1-ethoxyethoxy)pent-3-yn-2-ol
• CAS: 171019-46-8
• 化学式: C₉H₁₆O₃
• 分子量: 172.224
• InChiKey: UWGFEUHZLOIAIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  rac-5-(1-ethoxyethoxy)-3-pentyn-2-ol 生成 (S)-5-(1-ethoxyethoxy)-3-pentyn-2-ol
  参考文献：
  名称：

  Enzyme catalysed irreversible transesterifications with vinyl acetate. Are they really irreversible?

  摘要：

  When racemic beta-methyl-(2-thiophene)propanol (1) was resolved via transesterification catalysed by lipase from Pseudomonas fluorescens (PFL) using an excess vinyl acetate in chloroform the enantioselectivity was high E approximate to 200 (conversion, c = 39%) when calculated from the ee of the (S)-ester S-1Ac. However, based on the ee of the remaining (R)-alcohol R-1, assuming irreversibility and when measured at c = 57%, E = 37 was obtained. Similarly, when the 5-(1-ethoxyethoxy)-3-pentyn-2-ol (2) was resolved using immobilised lipase B from Candida antarctica (Novozym SP435) under similar conditions, the (R)-ester product R-2Ac at c = 22% gave E approximate to 140 compared with that of the remaining alcohol S-2 at c = 65% which gave E = 15. These results are interpreted as a consequence of a reversible process occurring in transesterifications of this type, which are commonly referred to as irreversible.

  DOI：

  10.1016/0957-4166(95)00298-4
• 作为产物：
  描述：

  3-(1-乙氧基乙氧基)-1-丙炔 、 乙醛 在 正丁基锂 作用下， 生成 rac-5-(1-ethoxyethoxy)-3-pentyn-2-ol
  参考文献：
  名称：

  Enzyme catalysed irreversible transesterifications with vinyl acetate. Are they really irreversible?

  摘要：

  When racemic beta-methyl-(2-thiophene)propanol (1) was resolved via transesterification catalysed by lipase from Pseudomonas fluorescens (PFL) using an excess vinyl acetate in chloroform the enantioselectivity was high E approximate to 200 (conversion, c = 39%) when calculated from the ee of the (S)-ester S-1Ac. However, based on the ee of the remaining (R)-alcohol R-1, assuming irreversibility and when measured at c = 57%, E = 37 was obtained. Similarly, when the 5-(1-ethoxyethoxy)-3-pentyn-2-ol (2) was resolved using immobilised lipase B from Candida antarctica (Novozym SP435) under similar conditions, the (R)-ester product R-2Ac at c = 22% gave E approximate to 140 compared with that of the remaining alcohol S-2 at c = 65% which gave E = 15. These results are interpreted as a consequence of a reversible process occurring in transesterifications of this type, which are commonly referred to as irreversible.

  DOI：

  10.1016/0957-4166(95)00298-4

文献信息

• Enzyme catalysed irreversible transesterifications with vinyl acetate. Are they really irreversible?
  作者：Mårten Lundh、Ove Nordin、Erik Hedenström、Hans-Erik Högberg

  DOI：10.1016/0957-4166(95)00298-4

  日期：1995.9

  When racemic beta-methyl-(2-thiophene)propanol (1) was resolved via transesterification catalysed by lipase from Pseudomonas fluorescens (PFL) using an excess vinyl acetate in chloroform the enantioselectivity was high E approximate to 200 (conversion, c = 39%) when calculated from the ee of the (S)-ester S-1Ac. However, based on the ee of the remaining (R)-alcohol R-1, assuming irreversibility and when measured at c = 57%, E = 37 was obtained. Similarly, when the 5-(1-ethoxyethoxy)-3-pentyn-2-ol (2) was resolved using immobilised lipase B from Candida antarctica (Novozym SP435) under similar conditions, the (R)-ester product R-2Ac at c = 22% gave E approximate to 140 compared with that of the remaining alcohol S-2 at c = 65% which gave E = 15. These results are interpreted as a consequence of a reversible process occurring in transesterifications of this type, which are commonly referred to as irreversible.