4-(2-Methyl-1,3-benzodioxol-2-yl)butanal | 51308-14-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 4-(2-Methyl-1,3-benzodioxol-2-yl)butanal
• CAS: 51308-14-6
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: OPDIMPXZHBWAMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  羟基丙酮 、 4-(2-Methyl-1,3-benzodioxol-2-yl)butanal 在 PBS buffer 、 aldolase antibody 38C₂ (Aldrich no. 47,995-0) 作用下， 以 乙腈 为溶剂， 反应 36.0h， 以55%的产率得到(3R,4S)-3,4-Dihydroxy-7-(2-methyl-benzo[1,3]dioxol-2-yl)-heptan-2-one
  参考文献：
  名称：

  Enantioselective Total Synthesis of Some Brevicomins Using Aldolase Antibody 38C2

  摘要：

  Aldolase antibody 38C2 (Aldrich no. 47,995-0) catalyzes the aldol reaction between hydroxyacetone and aldehyde 7 to give dihydroxyketone 8 alpha in an enantiomeric excess (ee) >99%. This reaction has been performed on a semipreparative scale to give the product in 55% yield (ee=98%). Aldol 8 alpha can be converted to hydroxybrevicomins ent-5 and ent-6 by reduction and acid-catalyzed cyclization. Antibody 38C2 also catalyzes the retro-aldol reaction of racemic syn-8. After 52% conversion, the enantiomeric product (8 beta) is obtained in >99% ee. By using either antibody-catalyzed aldol or retro-aldol reactions, both aldol enantiomers can be prepared with a single antibody catalyst. This methodology has been applied in highly enantioselective total syntheses of ten brevicomins.

  DOI：

  10.1002/(sici)1521-3765(19980515)4:5<881::aid-chem881>3.0.co;2-#
• 作为产物：
  描述：

  5-酮基已腈 在 二异丁基氢化铝 、 对甲苯磺酸 作用下， 以 正己烷 、 二氯甲烷 、 苯 为溶剂， 反应 15.0h， 生成 4-(2-Methyl-1,3-benzodioxol-2-yl)butanal
  参考文献：
  名称：

  Enantioselective Total Synthesis of Some Brevicomins Using Aldolase Antibody 38C2

  摘要：

  Aldolase antibody 38C2 (Aldrich no. 47,995-0) catalyzes the aldol reaction between hydroxyacetone and aldehyde 7 to give dihydroxyketone 8 alpha in an enantiomeric excess (ee) >99%. This reaction has been performed on a semipreparative scale to give the product in 55% yield (ee=98%). Aldol 8 alpha can be converted to hydroxybrevicomins ent-5 and ent-6 by reduction and acid-catalyzed cyclization. Antibody 38C2 also catalyzes the retro-aldol reaction of racemic syn-8. After 52% conversion, the enantiomeric product (8 beta) is obtained in >99% ee. By using either antibody-catalyzed aldol or retro-aldol reactions, both aldol enantiomers can be prepared with a single antibody catalyst. This methodology has been applied in highly enantioselective total syntheses of ten brevicomins.

  DOI：

  10.1002/(sici)1521-3765(19980515)4:5<881::aid-chem881>3.0.co;2-#

文献信息

• Enantioselective Total Synthesis of Some Brevicomins Using Aldolase Antibody 38C2
  作者：Benjamin List、Doron Shabat、Carlos F. Barbas III、Richard A. Lerner

  DOI：10.1002/(sici)1521-3765(19980515)4:5<881::aid-chem881>3.0.co;2-#

  日期：1998.5.15

  Aldolase antibody 38C2 (Aldrich no. 47,995-0) catalyzes the aldol reaction between hydroxyacetone and aldehyde 7 to give dihydroxyketone 8 alpha in an enantiomeric excess (ee) >99%. This reaction has been performed on a semipreparative scale to give the product in 55% yield (ee=98%). Aldol 8 alpha can be converted to hydroxybrevicomins ent-5 and ent-6 by reduction and acid-catalyzed cyclization. Antibody 38C2 also catalyzes the retro-aldol reaction of racemic syn-8. After 52% conversion, the enantiomeric product (8 beta) is obtained in >99% ee. By using either antibody-catalyzed aldol or retro-aldol reactions, both aldol enantiomers can be prepared with a single antibody catalyst. This methodology has been applied in highly enantioselective total syntheses of ten brevicomins.