(4-nitrophenyl)-acetic anhydride | 1760-47-0

• 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: (4-nitrophenyl)-acetic anhydride
• 英文别名: (4-nitro-phenyl)-acetic acid-anhydride；(4-Nitro-phenyl)-essigsaeure-anhydrid；4-Nitrophenylessigsaeureanhydrid；Benzeneacetic acid, 4-nitro-, anhydride with 4-nitrobenzeneacetic acid；[2-(4-nitrophenyl)acetyl] 2-(4-nitrophenyl)acetate
• CAS: 1760-47-0
• 化学式: C₁₆H₁₂N₂O₇
• 分子量: 344.28
• InChiKey: LKHMSUATUYVXSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  135
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,5-二脱氧腺苷 、 (4-nitrophenyl)-acetic anhydride 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以26 mg的产率得到3'-<(4-nitrophenyl)-acetyl>-2',5'-dideoxyadenosine
  参考文献：
  名称：

  Synthesis of Iodo-aryl-azido Adenosine Analogs as Affinity Ligands for Adenylyl Cyclase

  摘要：

  Potential affinity probes for adenylyl cyclase were synthesized that take advantage of the enzyme's sensitivity to ''P''-site-mediated inhibition by 2',5'-dideoxyadenosine analogs and its tolerance for large 3'-ribose substitutions. We report the synthesis of a series of 3'-substituted 2',5'-dideoxyadenosine analogs. The syntheses involved the intermediate formation of symmetric anhydrides that were then coupled to 2',5'-dideoxyadenosine by base-catalyzed esterification at the 3'-ribose position.

  DOI：

  10.1080/15257779408010676
• 作为产物：
  描述：

  对硝基苯乙酸 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (4-nitrophenyl)-acetic anhydride
  参考文献：
  名称：

  Synthesis of Iodo-aryl-azido Adenosine Analogs as Affinity Ligands for Adenylyl Cyclase

  摘要：

  Potential affinity probes for adenylyl cyclase were synthesized that take advantage of the enzyme's sensitivity to ''P''-site-mediated inhibition by 2',5'-dideoxyadenosine analogs and its tolerance for large 3'-ribose substitutions. We report the synthesis of a series of 3'-substituted 2',5'-dideoxyadenosine analogs. The syntheses involved the intermediate formation of symmetric anhydrides that were then coupled to 2',5'-dideoxyadenosine by base-catalyzed esterification at the 3'-ribose position.

  DOI：

  10.1080/15257779408010676

文献信息

• process for the preparation of optically-active cyanomethyl esters
  申请人：E.I. DU PONT DE NEMOURS AND COMPANY

  公开号：EP0109681A2

  公开（公告）日：1984-05-30

  Stereoisomerically-enriched cyanomethyl esters are prepared by treating a non-symmetrical ketene or an alpha-chiral carboxylic acid halide or reactive derivative thereof with an optically-active alphahydroxynitrile. Certain optically-active optionally substituted S-alphacyano-3-phenoxybenzyl alcohol intermediates are prepared by treating the corresponding aldehyde of ketone with a source of hydrogen cyanide in the presence of a substantially water-immiscible, aprotic solvent and a cyclo(D-phenylalanyl-D-histidine) as a catalyst.

  通过将非对称酮或α-手性羧酸卤化物或其活性衍生物与具有光学活性的α-羟腈进行处理，可制备立体异构体富集的氰甲基酯。某些具有光学活性的任选取代的 S-alphacyano-3-苯氧基苄醇中间体的制备方法是：在基本上不溶于水的壬烷溶剂和作为催化剂的环(D-苯丙氨酰-D-组氨酸)存在下，用氰化氢源处理相应的酮醛。
• Process for the preparation of optically-active cyanomethyl esters
  申请人：E.I. DU PONT DE NEMOURS AND COMPANY

  公开号：EP0291626A2

  公开（公告）日：1988-11-23

  Stereoisomerically-enriched cyanomethyl esters are prepared by treating a non-symmetrical ketene or an alpha-chiral carboxylic acid halide or reactive derivative thereof with an optically-active alpha-hydroxynitrile. Certain optically-active optionally substituted S-alpha-cyano-3-phenoxybenzyl alcohol intermediates are prepared by treating the corresponding aldehyde or ketone with a source of hydrogen cyanide in the presence of a substantially water-immiscible, aprotic solvent and a cyclo(D-phenylalanyl-D-histidine) as a catalyst.

  立体异构体富集氰基甲酯的制备方法是用光学活性的 α-羟腈处理非对称酮或α-手性羧酸卤化物或其活性衍生物。某些具有光学活性的任选取代的 S-α-氰基-3-苯氧基苄醇中间体的制备方法是：在基本上不溶于水的壬烷溶剂和作为催化剂的环(D-苯丙氨酰-D-组氨酸)存在下，用氰化氢源处理相应的醛或酮。
• Cyclo(D-phenylalanyl-D-histidine)
  申请人：E.I. DU PONT DE NEMOURS AND COMPANY

  公开号：EP0451927A1

  公开（公告）日：1991-10-16

  Cyclo(D-phenylalanyl-D-histidine) can be used as a catalyst in the preparation of an optically-active, optionally substituted S-alpha-cyano-3-phenoxy benzyl alcohol.

  环(D-苯丙氨酰-D-组氨酸)可用作催化剂，用于制备光学活性的、任选取代的 S-α-氰基-3-苯氧基苄醇。
• A Novel Rearrangement of o-Nitrophenylacetic Acids
  作者：Gordon N. Walker

  DOI：10.1021/ja01629a120

  日期：1955.12
• 22. The action of phosphorus pentachloride on non-symmetrically substituted acetones
  作者：Ahmad Zaki、Youssef Iskander

  DOI：10.1039/jr9430000068

  日期：——