(E)-2,2-dimethyl-5-phenyl-5-(2-butenyl)-1,3-dioxolan-4-one | 136962-22-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-2,2-dimethyl-5-phenyl-5-(2-butenyl)-1,3-dioxolan-4-one
• 英文别名: (Z)-2,2-dimethyl-5-phenyl-5-(2-butenyl)-1,3-dioxolan-4-one；2,2-dimethyl-5-phenyl-5-(2-butenyl)-1,3-dioxolan-4-one
• CAS: 136962-22-6；136962-23-7
• 化学式: C₁₅H₁₈O₃
• 分子量: 246.306
• InChiKey: MGQJAYGWKQWXBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.16
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (E)-2,2-dimethyl-5-phenyl-5-(2-butenyl)-1,3-dioxolan-4-one 在 lithium aluminium tetrahydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 5-(4-Chlorophenyl)-2,2-dimethyl-5-prop-2-enyl-1,3-dioxolan-4-one
  参考文献：
  名称：

  Lipase AKG mediated resolutions of α,α-disubstituted 1,2-diols in organic solvents; remarkably high regio- and enantio-selectivity

  摘要：

  Diols 1, which contain adjacent tertiary and primary hydroxy groups, can be selectively mono-acylated at the primary hydroxy group by many lipases in organic solvents, Since the reaction does not take place at the chiral tertiary centre itself, observed enantioselectivities are usually low. Only the combination of one lipase, lipase AKG (Amano, Pseudomonas sp.), with selected substrates gives high enantioselectivities (E 20 to > 200), Also, the solvent and acyl donor employed influences the outcome, On the basis of the results of Lipase AKG towards substrates 1 an active site model for this specific lipase has been developed, which can account for the results obtained, Fu!! experimental details on the synthesis of diols 1 and enzymatic preparation of acetates 2 are given, Also, the absolute stereochemistry of the enzymatically prepared diols 1 has been established by independent synthesis from (R)-mandelic acid.

  DOI：

  10.1039/p19960002051
• 作为产物：
  描述：

  1-溴-2-丁烯 、 2,2-二甲基-5-苯基-1,3-二氧杂烷-4-酮 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 (E)-2,2-dimethyl-5-phenyl-5-(2-butenyl)-1,3-dioxolan-4-one
  参考文献：
  名称：

  Lipase AKG mediated resolutions of α,α-disubstituted 1,2-diols in organic solvents; remarkably high regio- and enantio-selectivity

  摘要：

  Diols 1, which contain adjacent tertiary and primary hydroxy groups, can be selectively mono-acylated at the primary hydroxy group by many lipases in organic solvents, Since the reaction does not take place at the chiral tertiary centre itself, observed enantioselectivities are usually low. Only the combination of one lipase, lipase AKG (Amano, Pseudomonas sp.), with selected substrates gives high enantioselectivities (E 20 to > 200), Also, the solvent and acyl donor employed influences the outcome, On the basis of the results of Lipase AKG towards substrates 1 an active site model for this specific lipase has been developed, which can account for the results obtained, Fu!! experimental details on the synthesis of diols 1 and enzymatic preparation of acetates 2 are given, Also, the absolute stereochemistry of the enzymatically prepared diols 1 has been established by independent synthesis from (R)-mandelic acid.

  DOI：

  10.1039/p19960002051

文献信息

• PLE catalyzed hydrolyses of α-substituted α-hydroxy esters: The influence of the substituents.
  作者：Henk Moorlag、Richard M. Kellogg

  DOI：10.1016/s0957-4166(00)86125-x

  日期：1991.1

  The enzymatic hydrolyses of a variety of α-substituted mandelic and lactic esters using pig liver esterase (PLE) have been investigated. High to moderate enantioselectivity was found for various α-substituted mandelic esters, whereas PLE showed low to no enantioselectivity for α-substituted lactic esters. We observed that the enantioselectivity of PLE depends strongly on the length and nature of the

  已经研究了使用猪肝酯酶（PLE）酶促水解各种α-取代的扁桃酸酯和乳酸酯的方法。发现对各种α-取代的扁桃酸酯具有高到中等的对映选择性，而PLE对α-取代的乳酸酯显示出低至没有对映选择性。我们观察到，PLE的对映选择性很大程度上取决于α位置取代基的长度和性质。讨论了PLE的活动站点模型的一些后果。