6-(4'-acetamidophenyl)-3-hexen-2-one | 169053-99-0

• 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: 6-(4'-acetamidophenyl)-3-hexen-2-one
• 英文别名: N-[4-[(E)-5-oxohex-3-enyl]phenyl]acetamide
• CAS: 169053-99-0
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: AWSKTSJCISGWOR-HWKANZROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-(4'-acetamidophenyl)-3-hexen-2-one 在 palladium dichloride 水 、 四氯化钛 、 copper(l) chloride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-[4-[5-oxo-3-(2-oxopropyl)hexyl]phenyl]acetamide
  参考文献：
  名称：

  Enantioselective Aldol Cyclodehydrations Catalyzed by Antibody 38C2

  摘要：

  Aldolase antibody 38C2 catalyzes the enantioselective aldol cyclodehydration of 4-substituted-2,6-heptanediones (3) to give enantiomerically enriched 5-substituted-3-methyl-2-cyclohexen-1-ones (4). Yields, enantioselectivities, and product purities are markedly increased compared to the L-proline-catalyzed reactions.

  DOI：

  10.1021/ol9905405
• 作为产物：
  描述：

  N-(4-碘苯基)乙酰胺 在 盐酸甲胺 、 palladium dichloride N-甲基吡咯烷酮 、 sodium hydroxide 、 phosphate buffer 、 碳酸氢钠 作用下， 反应 124.0h， 生成 6-(4'-acetamidophenyl)-3-hexen-2-one
  参考文献：
  名称：

  Catalytic, Enantioselective Aldol Reaction with an Artificial Aldolase Assembled from a Primary Amine and an Antibody

  摘要：

  The aldol addition of acetone to aldehydes 1-5 is catalyzed by primary amine 14. The pH profile is consistent with catalysis by the free amine, with pK(a) = 8.55 for its conjugate acid. The catalytic cycle involves rate-determining coupling of the aldehyde with enamine III formed by condensation of the amine and acetone, Condensation with the aldehyde to form imine 16 inhibits catalysis (K-16 = 7.8 mM). Assembly of amine 14 with an antibody against quaternary ammonium hapten 19 yields an artificial aldolase which catalyzes the reaction. The catalyst is approximately 600 times more reactive than amine 14 alone. The pK(a) of the amino group is unchanged within the complex. The antibody catalyzes the formation of amino nitrile 17 in the presence of cyanide, suggesting that condensation of acetone with amine 14 is favored by complexation with the antibody, an effect which might account for catalysis. The reaction with aldehyde 1 is si enantioface selective and gives aldol (SS)-6 (>95% de) from (S)-1 and aldol (RS)-6 from (R)-1 (65% de) in a 1:2.8 ratio. These experiments show the principles of a novel approach for the design of an artificial aldolase.

  DOI：

  10.1021/jo00126a057

文献信息

• Catalytic, Enantioselective Aldol Reaction with an Artificial Aldolase Assembled from a Primary Amine and an Antibody
  作者：Jean-Louis Reymond、Yuanwei Chen

  DOI：10.1021/jo00126a057

  日期：1995.10

  The aldol addition of acetone to aldehydes 1-5 is catalyzed by primary amine 14. The pH profile is consistent with catalysis by the free amine, with pK(a) = 8.55 for its conjugate acid. The catalytic cycle involves rate-determining coupling of the aldehyde with enamine III formed by condensation of the amine and acetone, Condensation with the aldehyde to form imine 16 inhibits catalysis (K-16 = 7.8 mM). Assembly of amine 14 with an antibody against quaternary ammonium hapten 19 yields an artificial aldolase which catalyzes the reaction. The catalyst is approximately 600 times more reactive than amine 14 alone. The pK(a) of the amino group is unchanged within the complex. The antibody catalyzes the formation of amino nitrile 17 in the presence of cyanide, suggesting that condensation of acetone with amine 14 is favored by complexation with the antibody, an effect which might account for catalysis. The reaction with aldehyde 1 is si enantioface selective and gives aldol (SS)-6 (>95% de) from (S)-1 and aldol (RS)-6 from (R)-1 (65% de) in a 1:2.8 ratio. These experiments show the principles of a novel approach for the design of an artificial aldolase.
• Enantioselective Aldol Cyclodehydrations Catalyzed by Antibody 38C2
  作者：Benjamin List、Richard A. Lerner、Carlos F. Barbas

  DOI：10.1021/ol9905405

  日期：1999.7.1

  Aldolase antibody 38C2 catalyzes the enantioselective aldol cyclodehydration of 4-substituted-2,6-heptanediones (3) to give enantiomerically enriched 5-substituted-3-methyl-2-cyclohexen-1-ones (4). Yields, enantioselectivities, and product purities are markedly increased compared to the L-proline-catalyzed reactions.