4-benzeneacetaldehyde | 134485-53-3

• 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: 4-benzeneacetaldehyde
• 英文别名: 2-[4-(Dibenzylamino)phenyl]acetaldehyde
• CAS: 134485-53-3
• 化学式: C₂₂H₂₁NO
• 分子量: 315.415
• InChiKey: DWHLXLWWTBXEFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-benzeneacetaldehyde 在 palladium on activated charcoal 正丁基锂 、 氢气 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， -78.0~25.0 ℃ 、344.73 kPa 条件下， 反应 10.5h， 生成 戊酸,5-[[4-[2-羟基-2-(2-甲基苯基)乙基]苯基]氨基]-5-羰基-
  参考文献：
  名称：

  Antibody bait and switch catalysis: a survey of antigens capable of inducing abzymes with acyl-transfer properties

  摘要：

  Antibodies have been shown to catalyze acyl-transfer reactions. Various antigens have been applied to these hydrolytic reactions, but typically all encompass the same theme of incorporating a monoanionic phosphonate/phosphonamidate. To expand the scope and capabilities of these abzymes, we have directed our attention toward new strategies in antigen design. One method, which we have termed ''bait and switch'' catalysis, uses haptens to elicit amino acid(s) within the binding pocket of an antibody that can accelerate hydrolysis. We reported initial success of this methodology utilizing the cationic hapten 1 for obtaining abzymes that hydrolyzed benzoate ester 6. In addition, we showed how the structurally identical but neutral hapten 2 was unable to induce catalytic antibodies. To further identify those factors critical in the generation of hydrolytic abzymes via our bait and switch methodology, we have (1) designed and synthesized three new homologues of 1 in which we have varied the type of charge/no charge and its location, (2) screened and identified catalytic antibodies from these antigens, (3) determined affinity constants of a number of these monoclonal antibodies (catalytic and noncatalytic) for their respective haptens and possible substrates (ester/amide), (4) performed steady-state kinetics, inducing a pH-rate profile on one of these abzymes, and (5) used chemical modifying reagents to identify which amino acid residue(s) are involved in these catalytic processes.

  DOI：

  10.1021/ja00014a039
• 作为产物：
  描述：

  4-硝基苯乙烯 在 palladium on activated charcoal lead(IV) acetate 、 盐酸 、 calcium sulfate 、 Rexyn 101 (H) cation-exchange resin 、 氢气 、 三乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 58.0h， 生成 4-benzeneacetaldehyde
  参考文献：
  名称：

  Antibody bait and switch catalysis: a survey of antigens capable of inducing abzymes with acyl-transfer properties

  摘要：

  Antibodies have been shown to catalyze acyl-transfer reactions. Various antigens have been applied to these hydrolytic reactions, but typically all encompass the same theme of incorporating a monoanionic phosphonate/phosphonamidate. To expand the scope and capabilities of these abzymes, we have directed our attention toward new strategies in antigen design. One method, which we have termed ''bait and switch'' catalysis, uses haptens to elicit amino acid(s) within the binding pocket of an antibody that can accelerate hydrolysis. We reported initial success of this methodology utilizing the cationic hapten 1 for obtaining abzymes that hydrolyzed benzoate ester 6. In addition, we showed how the structurally identical but neutral hapten 2 was unable to induce catalytic antibodies. To further identify those factors critical in the generation of hydrolytic abzymes via our bait and switch methodology, we have (1) designed and synthesized three new homologues of 1 in which we have varied the type of charge/no charge and its location, (2) screened and identified catalytic antibodies from these antigens, (3) determined affinity constants of a number of these monoclonal antibodies (catalytic and noncatalytic) for their respective haptens and possible substrates (ester/amide), (4) performed steady-state kinetics, inducing a pH-rate profile on one of these abzymes, and (5) used chemical modifying reagents to identify which amino acid residue(s) are involved in these catalytic processes.

  DOI：

  10.1021/ja00014a039

文献信息

• JANDA, KIM D.;WEINHOUSE, MICHAEL I.;DANON, TAMI;PACELLI, KAREN A.;SCHLOED+, J. AMER. CHEM. SOC., 113,(1991) N4, C. 5427-5434
  作者：JANDA, KIM D.、WEINHOUSE, MICHAEL I.、DANON, TAMI、PACELLI, KAREN A.、SCHLOED+

  DOI：——

  日期：——
• Antibody bait and switch catalysis: a survey of antigens capable of inducing abzymes with acyl-transfer properties
  作者：Kim D. Janda、Michael I. Weinhouse、Tami Danon、Karen A. Pacelli、Diane M. Schloeder

  DOI：10.1021/ja00014a039

  日期：1991.7

  Antibodies have been shown to catalyze acyl-transfer reactions. Various antigens have been applied to these hydrolytic reactions, but typically all encompass the same theme of incorporating a monoanionic phosphonate/phosphonamidate. To expand the scope and capabilities of these abzymes, we have directed our attention toward new strategies in antigen design. One method, which we have termed ''bait and switch'' catalysis, uses haptens to elicit amino acid(s) within the binding pocket of an antibody that can accelerate hydrolysis. We reported initial success of this methodology utilizing the cationic hapten 1 for obtaining abzymes that hydrolyzed benzoate ester 6. In addition, we showed how the structurally identical but neutral hapten 2 was unable to induce catalytic antibodies. To further identify those factors critical in the generation of hydrolytic abzymes via our bait and switch methodology, we have (1) designed and synthesized three new homologues of 1 in which we have varied the type of charge/no charge and its location, (2) screened and identified catalytic antibodies from these antigens, (3) determined affinity constants of a number of these monoclonal antibodies (catalytic and noncatalytic) for their respective haptens and possible substrates (ester/amide), (4) performed steady-state kinetics, inducing a pH-rate profile on one of these abzymes, and (5) used chemical modifying reagents to identify which amino acid residue(s) are involved in these catalytic processes.