(E,Z)-2-acetyl-3-methoxy-but-2-enoic acid ethyl ester

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: (E,Z)-2-acetyl-3-methoxy-but-2-enoic acid ethyl ester
• 英文别名: ethyl (Z)-2-acetyl-3-methoxybut-2-enoate
• 化学式: C₉H₁₄O₄
• 分子量: 186.208
• InChiKey: GLAPXQNIQSGRRS-FPLPWBNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E,Z)-2-acetyl-3-methoxy-but-2-enoic acid ethyl ester 在 sodium hydroxide 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 生成 4,6-二甲基嘧啶-5-甲酸
  参考文献：
  名称：

  Oximino-piperidino-piperidine-based CCR5 antagonists. Part 2: synthesis, SAR and biological evaluation of symmetrical heteroaryl carboxamides

  摘要：

  The synthesis, SAR and biological evaluation of symmetrical amide analogues of our clinical candidate SCH 351125 are described. A series of potent and orally bioavailable CCR5 antagonists containing symmetrical 2,6-dimethyl isonicotinamides and 2, 6-dimethyl pyrimidines amides were generated with enhanced affinity for the CCR5 receptor. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)01063-6
• 作为产物：
  描述：

  三氟甲烷磺酸甲酯 、 二乙酰乙酸乙酯 在 caesium carbonate 作用下， 以 乙腈 为溶剂， 以58%的产率得到(E,Z)-2-acetyl-3-methoxy-but-2-enoic acid ethyl ester
  参考文献：
  名称：

  Oximino-piperidino-piperidine-based CCR5 antagonists. Part 2: synthesis, SAR and biological evaluation of symmetrical heteroaryl carboxamides

  摘要：

  The synthesis, SAR and biological evaluation of symmetrical amide analogues of our clinical candidate SCH 351125 are described. A series of potent and orally bioavailable CCR5 antagonists containing symmetrical 2,6-dimethyl isonicotinamides and 2, 6-dimethyl pyrimidines amides were generated with enhanced affinity for the CCR5 receptor. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)01063-6

文献信息

• NOVEL BIARYL DERIVATIVES
  申请人：Aebi Johannes

  公开号：US20090048238A1

  公开（公告）日：2009-02-19

  The invention is concerned with novel biaryl derivatives of formula (I), wherein m, R 1 , R 2 , R 3 , X 1 , X 2 and X 3 are as defined in the description and in the claims, as well as physiologically acceptable salts thereof. These compounds are antagonists of CCR-2 receptor, CCR-5 receptor and/or CCR-3 receptor and can be used as medicaments.

  这项发明涉及式(I)的新型联苯衍生物，其中m、R1、R2、R3、X1、X2和X3如描述和权利要求中所定义，并且其生理上可接受的盐。这些化合物是CCR-2受体、CCR-5受体和/或CCR-3受体的拮抗剂，可用作药物。
• N-HETEROCYCLIC BIARYL CARBOXAMIDES AS CCR RECEPTOR ANTAGONISTS
  申请人：F. Hoffmann-La Roche AG

  公开号：EP2205583A2

  公开（公告）日：2010-07-14
• US8153805B2
  申请人：——

  公开号：US8153805B2

  公开（公告）日：2012-04-10
• [EN] NEW BIARYL DERIVATIVES<br/>[FR] NOUVEAUX DÉRIVÉS DE BIARYLE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2009043747A2

  公开（公告）日：2009-04-09

  The invention is concerned with novel biaryl derivatives of Formula (I), wherein Formula (A), m, R1, R2, R3, X1, X2 and X3 are as defined in the description and in the claims, as well as physiologically acceptable salts thereof. These compounds are antagonists of CCR-2 receptor, CCR-5 receptor and/or CCR-3 receptor and can be used as medicaments.
• Oximino-piperidino-piperidine-based CCR5 antagonists. Part 2: synthesis, SAR and biological evaluation of symmetrical heteroaryl carboxamides
  作者：Anandan Palani、Sherry Shapiro、John W. Clader、William J. Greenlee、Susan Vice、Stuart McCombie、Kathleen Cox、Julie Strizki、Bahige M. Baroudy

  DOI：10.1016/s0960-894x(02)01063-6

  日期：2003.2

  The synthesis, SAR and biological evaluation of symmetrical amide analogues of our clinical candidate SCH 351125 are described. A series of potent and orally bioavailable CCR5 antagonists containing symmetrical 2,6-dimethyl isonicotinamides and 2, 6-dimethyl pyrimidines amides were generated with enhanced affinity for the CCR5 receptor. (C) 2003 Elsevier Science Ltd. All rights reserved.