4-甲基-2-氧代-2H-苯并吡喃-7-基戊酸酯 | 717-28-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 4-甲基-2-氧代-2H-苯并吡喃-7-基戊酸酯
• 英文名称: 2-Ketopiperazin-N,N'-diessigsaeure
• 英文别名: 2-Oxo-4-piperazin-diessigsaeure (3-KP)；2-oxo-1,4-piperazinediacetic acid；(2-oxo-piperazine-1,4-diyl)-bis-acetic acid；1,4-Piperazinediacetic acid, 2-oxo-；2-[4-(carboxymethyl)-3-oxopiperazin-1-yl]acetic acid
• CAS: 717-28-2
• 化学式: C₈H₁₂N₂O₅
• 分子量: 216.194
• InChiKey: FCXSSZUUTJINKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  98.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-甲基-2-氧代-2H-苯并吡喃-7-基戊酸酯 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 生成 [[2-(Bis-carboxymethyl-amino)-ethyl]-(4-vinyl-benzenesulfonyl)-amino]-acetic acid
  参考文献：
  名称：

  Chelating polymers. I. The synthesis and acid dissociation behavior of several N-(p-vinylbenzenesulfonyl)-substituted diaminopolyacetic acid monomers, monomeric analogues, and related intermediates

  摘要：

  两种新的螯合单体，N-(对乙烯基苯磺酰)1,2-二氨乙烷-N′,N′-二乙酸(SS-EDDA)和-N,N′,N′-三乙酸(SS-ED3A)酸，以及几种单体类似物和相关中间体已经制备。此外，已合成2-氧代-1-哌嗪乙酸(S-KP)、3-氧代-1-哌嗪乙酸(U-KP)和2-氧代-1,4-哌嗪二乙酸(3-KP)酸，并且已证明这些环戊酰胺与它们未取代的线性氨基酸类似物，乙二胺-N,N′-二乙酸(S-EDDA)、-N,N-二乙酸(U-EDDA)和-N,N,N′-三乙酸(ED3A)酸之间的相互转化。各种氨基酸的酸解离常数在25°C和μ=0.1 M(KNO3)下通过电位滴定确定，并将结果与相关化合物的氢离子亲和力进行比较。根据这些结果提出了所有化合物的解离方案。通过环化效应和相邻基团的归纳效应，对线性氨基酸和环戊酰胺的解离常数进行了理性解释。这些理性解释有助于澄清先前针对几种线性氨基酸提出的解离方案。

  DOI：

  10.1139/v70-023
• 作为产物：
  描述：

  溴乙酸 、 2-氧代-1-哌嗪乙酸 在 sodium hydroxide 作用下， 生成 4-甲基-2-氧代-2H-苯并吡喃-7-基戊酸酯
  参考文献：
  名称：

  Complexes possessing ortho ligating functionality

  摘要：

  揭示了一组具有正交配位功能的官能化胺螯合剂，与稀土类金属离子形成络合物。这些螯合剂具有一般公式##STR1##其中R.sup.'1、R.sup.'2、R.sup.'3、R.sup.'4、R.sup.'5和R.sup.'6、Z'和X均在规范中定义。此外，某些螯合剂-放射性核素络合物可以有效地用于制剂，用作治疗和/或诊断钙化肿瘤和/或缓解骨疼痛的剂。

  公开号：

  US05342604A1

文献信息

• Chelants possessing ortho ligating functionality and complexes thereof
  申请人：THE DOW CHEMICAL COMPANY

  公开号：EP0367223A2

  公开（公告）日：1990-05-09

  A group of functionalized amine chelants having ortho ligating functionality that form complexes with rare-earth type metal ions are disclosed. The complexes can be covalently attached to an antibody or antibody fragment and used for therapeutic and/or diagnostic purposes. In addition certain of the chelant-­radionuclide complexes can be effectively employed in compositions useful as therapeutic and/or diagnostic agents for calcific tumors and/or relief of bone pain.

  本发明公开了一组具有正交连接功能的官能化胺螯合剂，可与稀土类金属离子形成络合物。这些复合物可与抗体或抗体片段共价连接，用于治疗和/或诊断目的。此外，某些螯合态放射性核素复合物还可有效地应用于治疗和/或诊断钙化性肿瘤和/或缓解骨痛的组合物中。
• 1-Cyanomethyl-4-carboxymethyl-3-ketopiperazine, salts thereof, and process for their preparation
  申请人：HAMPSHIRE CHEMICAL CORP.

  公开号：EP0546868A1

  公开（公告）日：1993-06-16

  A novel intermediate useful in the synthesis of ethylenediaminetriacetic acid (ED3A) or its salts. N,N'-ethylenediaminediacetic acid (ED2AH₂) or a salt containing up to one equivalent of base cation is condensed with formaldehyde to form a stable cyclic intermediate. The addition of cyanide forms 1-cyanomethyl-4-carboxymethyl-3-keto-piperazine or a salt thereof (mononitrile-monoacid), which is a useful intermediate in the production of ED3A. The nitrile in aqueous solutions may be hydrolysed to form 2-oxo-1,4-piperazinediacetic acid (3KP) or salts thereof. In the presence of excess base, salts of ED3A are formed in excellent yield and purity.

  一种用于合成乙二胺三乙酸（ED3A）或其盐的新型中间体。N,N'-乙二胺三乙酸（ED2AH₂）或含有最多一个当量碱阳离子的盐与甲醛缩合形成稳定的环状中间体。氰化物的加入会形成 1-氰甲基-4-羧甲基-3-酮哌嗪或其盐类（单腈单酸），这是生产 ED3A 的有用中间体。水溶液中的腈可水解形成 2-氧代-1,4-哌嗪二乙酸（3KP）或其盐。在过量碱的存在下，ED3A 的盐类会以极高的产率和纯度形成。
• Ethylenediamine-N,N'-diacetic acid-N'-cyanomethyl, salts thereof, and their preparation
  申请人：HAMPSHIRE CHEMICAL CORP.

  公开号：EP0546866A2

  公开（公告）日：1993-06-16

  A novel intermediate useful in the synthesis of ethylenediaminetriacetic acid (ED3A) or its salts. A salt of N,N′-ethylenediaminediacetic acid (ED2AH₂) is condensed with formaldehyde to form a stable 5-membered ring intermediate. The addition of cyanide across this cyclic material forms ethylenediamine N,N′-diacetic acid-N′-cyanomethyl or salts thereof (mononitrile-diacid), which is a useful intermediate in the production of ED3A. The nitrile in aqueous solutions may be spontaneously cyclized to form 2-oxo-1,4-piperazinediacetic acid (3KP) or salts thereof. In the presence of excess base, salts of ED3A are formed in excellent yield and purity.

  一种可用于合成乙二胺三乙酸（ED3A）或其盐类的新型中间体。N,N′-乙二胺三乙酸（ED2AH₂）的一种盐与甲醛缩合形成稳定的五元环中间体。在这种环状物质上加入氰化物会形成乙二胺 N,N′-二乙酸-N′-氰基甲基或其盐类（一腈二酸），这是生产 ED3A 的有用中间体。水溶液中的腈可自发环化形成 2-氧代-1,4-哌嗪二乙酸（3KP）或其盐。在过量碱的存在下，ED3A 的盐类会以极高的产率和纯度生成。
• Preparation of ethylenediaminetriacetic acid
  申请人：HAMPSHIRE CHEMICAL CORP.

  公开号：EP0546867A2

  公开（公告）日：1993-06-16

  Synthesis of ethylenediaminctriacetic acid (ED3A) or its salts is disclosed. A salt of N,N'-ethylenediaminediacetic acid (ED2AH₂) is condensed with formaldehyde to form a stable 5-membered ring intermediate. The addition of cyanide across this cyclic material forms ethylenediamine N,N'-diacetic acid-N'-cyanomethyl or salts thereof (mononitrile-diacid). The nitrile in aqueous solutions may be spontaneously cyclized to form 2-oxo-1,4-piperazinediacetic acid (3KP) or salts thereof, which is the desired cyclic intermediate. In the presence of excess base, salts of ED3A are formed desired cyclic intermediate. In the presence of excess base, salts of ED3A are formed in excellent yield and purity. Alternatively, the starting material is ED2AHaXb, where x is a base cation, e.g., an alkali or alkaline earth metal, a is 1 to 2, and b is 0 to 1 in aqueous solutions. The reaction mixture also can be acidified to ensure complete formation of carboxymethyl-2-oxopiperazine (the lactam) prior to the reaction. Formaldehyde is added, essentially resulting in the hydroxymethyl derivative. On the addition of a cyanide source, 1-cyanomethyl-4-carboxymethyl-3-ketopiperazine (mononitrile diacid) or a salt thereof is formed. Upon the addition of any suitable base or acid, this material may be hydrolyzed to 3KP. The addition of a base will open this ring structure to form the salt of ED3A.

  本发明公开了乙二胺三乙酸（ED3A）或其盐的合成方法。N,N'-乙二胺二乙酸（ED2AH₂）的盐与甲醛缩合形成稳定的五元环中间体。在这种环状物质上加入氰化物会形成乙二胺 N,N'-二乙酸-N'-氰基甲基或其盐类（一腈二酸）。水溶液中的腈可自发环化形成 2-氧代-1,4-哌嗪二乙酸（3KP）或其盐类，这是所需的环状中间体。在过量碱存在的情况下，ED3A 的盐类会形成所需的环状中间体。在过量碱存在的情况下，ED3A 的盐类会以极高的产率和纯度形成。或者，起始原料为 ED2AHaXb，其中 x 是碱阳离子，如碱金属或碱土金属，a 为 1 至 2，b 在水溶液中为 0 至 1。反应混合物也可以酸化，以确保在反应前完全形成羧甲基-2-氧代哌嗪（内酰胺）。加入甲醛，基本上会生成羟甲基衍生物。加入氰源后，形成 1-氰甲基-4-羧甲基-3-酮哌嗪（单腈二酸）或其盐。在加入任何合适的碱或酸后，这种材料可水解为 3KP。加入碱会打开这个环结构，形成 ED3A 的盐。
• N-acyl-N,N'N'-ethylenediaminetriacetic acid derivatives and process for preparing same
  申请人：HAMPSHIRE CHEMICAL CORPORATION

  公开号：EP0629608A2

  公开（公告）日：1994-12-21

  N-acyl derivatives of ethylenediaminetriacetic acid and processes for preparing the same comprising reacting ethylenediaminetriacetic acid with acyl halide.

  乙二胺三乙酸的 N-酰基衍生物和制备工艺，包括乙二胺三乙酸与酰基卤反应。