6-(4'-acetamidophenyl)-4-hydroxy-5-methyl-2-hexanone

• 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)-4-hydroxy-5-methyl-2-hexanone
• 英文别名: N-[4-(3-hydroxy-2-methyl-5-oxohexyl)phenyl]acetamide
• 化学式: C₁₅H₂₁NO₃
• 分子量: 263.337
• InChiKey: KGYOSTFWAOEYLD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(4-碘苯基)乙酰胺 在 N-(hydroxyethyl)-4-(aminomethyl)benzamide 、 palladium dichloride N-甲基吡咯烷酮 、 N,N-二羟乙基甘氨酸 、 碳酸氢钠 、 sodium chloride 作用下， 反应 6.0h， 生成 6-(4'-acetamidophenyl)-4-hydroxy-5-methyl-2-hexanone
  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 using antibodies against a quaternary ammonium ion with a primary amine cofactor
  作者：Jean-Louis Reymond、Yuanwei Chen

  DOI：10.1016/0040-4039(95)00343-b

  日期：1995.4

  The enantioselective aldol addition of acetone to aldehydes is catalyzed by antibodies raised against a quaternary ammonium hapten using the corresponding primary amine as cofactor.
• ALDOLASE CATALYTIC ANTIBODY
  申请人：THE SCRIPPS RESEARCH INSTITUTE

  公开号：EP0870014B1

  公开（公告）日：2007-02-21
• ALDOL CONDENSATIONS BY CATALYTIC ANTIBODIES
  申请人：The Scripps Research Institute

  公开号：EP1038018A1

  公开（公告）日：2000-09-27
• EP1038018A4
  申请人：——

  公开号：EP1038018A4

  公开（公告）日：2004-10-13
• US6326176B1
  申请人：——

  公开号：US6326176B1

  公开（公告）日：2001-12-04