N-(1,2,2,2-四氯乙氧基羰基氧)琥珀酰亚胺 | 107960-02-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: N-(1,2,2,2-四氯乙氧基羰基氧)琥珀酰亚胺
• 中文别名: N-(1,2,2,2-四氯乙氧羰氧基)琥珀酰亚胺
• 英文名称: 1,2,2,2-tetrachloroethyl N-succinimidyl carbonate
• 英文别名: N-(1,2,2,2-Tetrachloroethoxycarbonyloxy)succinimide；(2,5-dioxopyrrolidin-1-yl) 1,2,2,2-tetrachloroethyl carbonate
• CAS: 107960-02-1
• 化学式: C₇H₅Cl₄NO₅
• 分子量: 324.932
• InChiKey: NZLNRXJWZWZVSG-UHFFFAOYSA-N

物化性质

• 熔点：
  110 °C

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2925190090

反应信息

• 作为反应物：
  描述：

  Boc-O-苄基-L-酪氨酸 、 N-(1,2,2,2-四氯乙氧基羰基氧)琥珀酰亚胺 在 N-甲基吗啉 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 以73%的产率得到N-[叔丁氧羰基]-O-(苄基)-L-酪氨酸琥珀酰亚胺基酯
  参考文献：
  名称：

  Novel preparation of N-protected amino acid active esters using 1,2,2,2-tetrachloroethyl carbonates

  摘要：

  DOI：

  10.1021/jo00388a005
• 作为产物：
  描述：

  N-羟基琥珀酰亚胺基氯甲酸酯 、 三氯乙醛 在 吡啶 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.0h， 以40%的产率得到N-(1,2,2,2-四氯乙氧基羰基氧)琥珀酰亚胺
  参考文献：
  名称：

  A Convenient New Route to 1-Haloalkyl Carbonates

  摘要：

  烷基（或烯基或芳基）1-卤代烷基碳酸酯可以通过在催化剂存在下，将醛与烷基（或烯基或芳基）碳酰卤（卤代甲酸酯）反应来方便地制备。

  DOI：

  10.1055/s-1988-27597

文献信息

• Process for synthesizing active esters of carboxylic acids
  申请人：Societe Nationale des Poudres et Explosifs

  公开号：US04782164A1

  公开（公告）日：1988-11-01

  The invention relates to a new process for preparing active esters or carboxylic acids, which consists in reacting a carboxylic acid, in the presence of an agent for binding hydrohalic acid, with a carbonate of formula: ##STR1## in which R.sup.1 denotes either a radical of formula ##STR2## in which R.sup.3 and R.sup.4, which may be identical or different, are not hydrogen atoms and denote organic radicals which may be substituted or unsubstituted and saturated or unsaturated, and may be or may not be bound to a polymer, and which can be joined together to form a hetero-cyclic system with the nitrogen atom, or a substituted or unsubstituted aryl radical which may or may not be bound to a polymer, R.sup.2 denotes a hydrogen atom, an aliphatic or cycloaliphatic radical which may be substituted or unsubstituted and saturated or unsaturated, or a substituted or unsubstituted aromatic radical, and X denotes a halogen atom. This process is especially useful for the synthesis of active esters of N-protected amino acids. The invention also relates to the new carbonates described above and the method of producing them, which consists in reacting an alpha-halogenated chloroformate of formula: R.sup.2 --CHX--O--COCl with an alcohol of formula R.sup.1 OH in an inert solvent medium of the presence of an organic or inorganic base.

  该发明涉及一种制备活性酯或羧酸的新工艺，其包括在存在结合氢卤酸的试剂的情况下，将羧酸与下式的碳酸酯反应：##STR1## 其中R.sup.1表示以下式的基团之一：##STR2## 其中R.sup.3和R.sup.4，可以相同也可以不同，不是氢原子，并且表示可以被取代或未取代、饱和或不饱和的有机基团，可以或不可以与聚合物结合，并且可以结合在一起形成与氮原子形成杂环系统的杂环系统，或者是可以或不可以与聚合物结合的取代或未取代芳基基团，R.sup.2表示氢原子、可以被取代或未取代、饱和或不饱和的脂肪或环脂基团，或者是取代或未取代的芳基基团，X表示卤素原子。该工艺特别适用于合成N-保护氨基酸的活性酯。该发明还涉及上述新碳酸酯及其制备方法，其包括在有机或无机碱的存在下，在惰性溶剂介质中，将下式的α-卤代氯甲酸酯：R.sup.2 --CHX--O--COCl 与下式的醇：R.sup.1 OH 反应。
• Electrosynthesis and characterization of biotin-functionalized poly(terthiophene) copolymers, and their response to avidin
  作者：Fouzi Mouffouk、Stewart J. Brown、Anna M. Demetriou、Simon J. Higgins、Richard J. Nichols、R. M. Gamini RajapakseOn leave from Department o、Stuart Reeman

  DOI：10.1039/b413974g

  日期：——

  Using a succinyl ester linker, a terthiophene bearing a pendant biotin hydrazide in the 3′ position (4-N′-[5-(4,6-dioxo-hexahydrothieno[3,4-c]pyrrol-3-yl)-pentanoyl]hydrazino}-4-oxo-butyric acid 2-[2,2′:5′,2″]terthiophen-3′-yl-ethyl ester, 4) has been prepared in three steps from 2-[2,2′:5′,2″]-terthiophen-3′-yl-ethanol, 2, via succinic acid mono-(2-[2,2′,5′,2″]-terthiophene-3′-yl-ethyl) ester, 3. Using the ‘oligomer as monomer’ approach, polyterthiophene (co)polymer films have been generated, on Pt, Au and ITO-coated glass working electrodes, by repetitive scan cyclic voltammetry of solutions of 2,2′:5′,2″-terthiophene, or either 3 or 4 along with 2,2′:5′,2″-terthiophene itself. These films have been characterized by cyclic voltammetry (CV), electrochemical impedance spectra (EIS) and in situ reflectance FTIR spectroscopy. FTIR spectroscopy suggests that the 2,2′:5′,2″-terthiophene : 4 copolymer contains intact biotin moieties. The incubation of poly-2,2′:5′,2″-terthiophene and 2,2′:5′,2″-terthiophene : 4 copolymer with aqueous buffer solutions, followed by transfer back to CH3CN/0.1 M TEAT, results in only small changes in the film CV, whereas exposure of the biotin-functionalized 2,2′:5′,2″-terthiophene : 4 copolymer to avidin causes drastic changes to its CV and its EIS, consistent with the binding of avidin by biotin resulting in restricted ion transfer to and from the polymer. The minimum amount of avidin which causes a detectable change in the electrochemistry of a 0.03 cm2 2,2′:5′,2″-terthiophene : 4 copolymer-modified electrode is 5 × 10−14 moles. Exposure of the 2,2′:5′,2″-terthiophene : 4 copolymer to excess bovine serum albumin in buffer causes only the same small changes in its electrochemistry as exposure to buffer alone, ruling out nonspecific adsorption as a cause of the electrochemical changes on avidin exposure.

  使用琥珀酰酯连接剂，在 3′位上带有生物素酰肼悬垂体的噻吩（4-N′-[5-(4,6-二氧代六氢噻吩并[3,4-c]吡咯-3-基)-戊酰基]酰肼}-4-氧代丁酸 2-[2,2′：4）由 2-[2,2′:5′,2″]-三噻吩-3′-基乙醇（2）通过琥珀酸单（2-[2,2′,5′,2″]-三噻吩-3′-基乙基）酯（3）分三步制备而成。通过对 2,2′:5′,2″-噻吩或 3 或 4 与 2,2′:5′,2″-噻吩本身的溶液进行重复扫描循环伏安法，利用 "低聚物为单体 "的方法，在涂有铂金、金和 ITO 的玻璃工作电极上生成了聚噻吩（共）聚合物薄膜。这些薄膜通过循环伏安法（CV）、电化学阻抗谱（EIS）和原位反射傅立叶变换红外光谱进行了表征。傅立叶变换红外光谱表明，2,2′:5′,2″-噻吩 : 4 共聚物含有完整的生物素分子。将聚-2,2′:5′,2″-噻吩和 2,2′:5′,2″-Terthiophene : 4 共聚物与缓冲水溶液孵育，然后转回到 CH3CN/0.而将生物素官能化的 2,2′:5′,2″-噻吩：4 共聚物暴露于阿维丁后，其 CV 和 EIS 会发生急剧变化。在 0.03 cm2 的 2,2′:5′,2″-噻吩：4 共聚物改性电极上引起可检测到的电化学变化的最小阿维丁量为 5 × 10-14 摩尔。将 2,2′:5′,2″-四联噻吩：4 共聚物暴露于缓冲液中过量的牛血清白蛋白，其电化学变化与单独暴露于缓冲液中的变化相同微小，排除了非特异性吸附导致阿维丁暴露时电化学变化的原因。
• Certain pyridyl hydrazines and hydrazides useful for protein labeling
  申请人：Johnson Matthey, Inc.

  公开号：US05206370A1

  公开（公告）日：1993-04-27

  Bifunctional aromatic compounds which are capable of linking metal ions to biologically useful molecules. The bifunctional compounds are characterized as having a hydrazine or hydrazide group and a protein reactive group. The hydrazine or hydrazide group may be protected as a lower alkyl hydrazone. Conjugates of the bifunctional compounds with macromolecules are also described and labelled macromolecules comprised of the conjugates and metal ions are provided. Additionally, a method is provided for forming a labelled macromolecule by reacting a conjugate with a metal species The compounds and method of this invention are particularly useful in the fields of biology and medicine for imaging and/or therapy.

  具有连接金属离子到生物有用分子的双官能团芳香化合物。这些双官能团化合物的特征是具有一个肼或肼酸基团和一个蛋白质反应基团。肼或肼酸基团可以作为较低的烷基肼酮进行保护。本发明还描述了双官能团化合物与大分子的结合物，并提供了由结合物和金属离子组成的标记大分子。此外，本发明还提供了一种通过将结合物与金属物种反应形成标记大分子的方法。本发明的化合物和方法在生物学和医学领域中特别适用于成像和/或治疗。
• Protein labelling
  申请人：AnorMed, Inc.

  公开号：US06217845B1

  公开（公告）日：2001-04-17

  Bifunctional aromatic compounds which are capable of linking metal ions to biologically useful molecules. The bifunctional compounds are characterized as having a hydrazine or hydrazide group and a protein reactive group. The hydrazine or hydrazide group may be protected as a lower alkyl hydrazone. Conjugates of the bifunctional compounds with macromolecules are also described and labelled macromolecules comprised of the conjugates and metal ions are provided. Additionally, a method is provided for forming a labelled macromolecule by reacting a conjugate with a metal species. The compounds and method of this invention are particularly useful in the fields of biology and medicine for imaging and/or therapy.

  具有双功能的芳香化合物，能够将金属离子与生物有用分子连接起来。这些双功能化合物的特点在于具有一个肼或肼酰基团和一个蛋白质反应性基团。肼或肼酰基团可以作为较低烷基肼酮保护。本发明还描述了与大分子结合的双功能化合物的共轭物，并提供了由共轭物和金属离子组成的标记大分子。此外，本发明还提供了一种通过将共轭物与金属物种反应形成标记大分子的方法。本发明的化合物和方法在生物学和医学领域的成像和/或治疗方面特别有用。
• INTERMEDIATE COMPOUND FOR SYNTHESIZING PHARMACEUTICAL AGENT AND PRODUCTION METHOD THEREOF
  申请人：OKUYAMA Masahiro

  公开号：US20110251385A1

  公开（公告）日：2011-10-13

  The present invention relates to a production method of an optically active morpholine compound represented by the formula 10, which includes the following steps: wherein each symbol is as defined in the specification. The present invention also relates to a production method of an compound represented by the formula 55, which includes the following steps: wherein each symbol is as defined in the specification. According to the production method of the present invention, an optically active 2-aryl-substituted morpholine compound and 3-oxo-3-(pyrimidin-4-yl)propionate, which are important as starting materials for synthesizing 2-(2-arylmorpholin-4-yl)-1-methyl-1H-[4,4′]bipyrimidinyl-6-one having a tau protein kinase 1 inhibitory activity and useful as a therapeutic drug for Alzheimer's disease and the like, can be produced in a high yield by an industrially advantageous method.

  本发明涉及一种光学活性吗啉化合物的生产方法，其由公式10表示，包括以下步骤：其中每个符号如规范中所定义。本发明还涉及一种由公式55表示的化合物的生产方法，其包括以下步骤：其中每个符号如规范中所定义。根据本发明的生产方法，可以通过一种工业上有利的方法高产地生产重要的起始材料，即光学活性2-芳基取代吗啉化合物和3-氧代-3-(嘧啶-4-基)丙酸酯，用于合成具有tau蛋白激酶1抑制活性的2-(2-芳基吗啉-4-基)-1-甲基-1H-[4,4′]联吡啶基-6-酮，该化合物对阿尔茨海默病等有用作用的治疗药物。