2-methoxybenzoic acid N-hydroxysuccinimide ester | 60586-99-4

• 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: 2-methoxybenzoic acid N-hydroxysuccinimide ester
• 英文别名: 2,5-dioxopyrrolidin-1-yl 2-methoxybenzoate；N-(2-methoxybenzoyloxy)succinimide；N-(2-Methoxybenzoyloxy)-succinimid；(2,5-Dioxopyrrolidin-1-yl) 2-methoxybenzoate
• CAS: 60586-99-4
• 化学式: C₁₂H₁₁NO₅
• mdl: MFCD00441399
• 分子量: 249.223
• InChiKey: WVWBRWURYGFKSZ-UHFFFAOYSA-N

物化性质

• 熔点：
  170-171 °C(Solv: ethanol (64-17-5))
• 沸点：
  396.8±44.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-methoxybenzoic acid N-hydroxysuccinimide ester 在 N,N-二异丙基乙胺 、 diborane(6) 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 34.0h， 生成 N,N'-二(2-甲氧基苄基氨基己基)胱胺
  参考文献：
  名称：

  Benextramine-neuropeptide Y受体的相互作用：苄基部分对[3H] neuropeptide Y置换活性的贡献。

  摘要：

  使用溶液相肽合成方法合成了N，N'-双[6-[（[2-甲氧基苄基）氨基]己-1-基]胱胺的类似物（benextramine，BXT，2），并分析了取代特异性结合的活性1 nM N- [丙酰-3H]神经肽Y（[3H] NPY）来自大鼠脑中对苯乙胺敏感的神经肽Y（NPY）结合位点。我们对这些类似物的新合成方法开始于，将胱胺与叔丁氧羰基（t-Boc）保护的6-氨基己酸的N-羟基琥珀酰亚胺酯酰化，然后用在二恶烷中的4 N HCl脱保护t-Boc基团。用适当取代的苯甲酸的N-羟基琥珀酰亚胺酯将该对称的二胺酰化，然后在回流的THF中用乙硼烷还原所得的四酰胺，得到目标化合物。缺乏苄基的BXT类似物（即化合物11）在浓度高达1.4 x 10（-3）M时没有[3H] NPY置换活性。邻位，间位和对位的活性范围是9倍在对苯达拉明敏感的NPY大鼠大脑结合位点的甲氧基，氯代和羟基苯达拉明类似物的区域异构体与在α-

  DOI：

  10.1021/jm00054a012
• 作为产物：
  描述：

  2-溴苯甲醚 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 水 、 乙腈 为溶剂， 生成 2-methoxybenzoic acid N-hydroxysuccinimide ester
  参考文献：
  名称：

  流动微反应器中极快的气体/液体反应：短寿命有机锂的羧基化

  摘要：

  在流动微反应器系统中，将带有亲电官能团（例如硝基，氰基和烷氧羰基）的短寿命有机锂与CO 2进行羧基化，生成羧酸和活性酯。成功的反应表明，气/液传质以及随后与CO 2的化学反应非常快。

  DOI：

  10.1002/chem.201402520

文献信息

• A versatile strategy for the design and synthesis of novel ADP conjugates and their evaluation as potential poly(ADP-ribose) polymerase 1 inhibitors
  作者：Yuliya V. Sherstyuk、Alexandra L. Zakharenko、Mikhail M. Kutuzov、Polina V. Chalova、Maria V. Sukhanova、Olga I. Lavrik、Vladimir N. Silnikov、Tatyana V. Abramova

  DOI：10.1007/s11030-016-9703-x

  日期：2017.2

  aromatic acid residue. A number of conjugates containing aromatic carboxylic acids were found to inhibit poly(ADP-ribose) synthesis catalyzed by poly(ADP-ribose) polymerase-1 (PARP-1). A new class of potential PARP-1 inhibitors mimicking \(\hbox NAD}^+}\), a substrate in the PARP-1 catalyzed reaction, was proposed. Graphical Abstract

  抽象的开发了一种合成\（\ hbox NAD} ^ +} \）模拟物的通用策略，该策略涉及在含有功能氨基的关键缀合物中有效的焦磷酸盐键形成，该功能键充当进一步衍生化的有用反应性锚。这些\（\ hbox NAD} ^ +} \）模拟物由通过二磷酸链共轭到带有芳族酸残基的扩展脂族连接基上的ADP组成。发现许多包含芳族羧酸的缀合物抑制由聚（ADP-核糖）聚合酶-1（PARP-1）催化的聚（ADP-核糖）合成。提出了一类新的潜在的PARP-1抑制剂，其模仿PARP-1催化反应的底物\（\ hbox NAD} ^ +} \）。 图形概要
• Iron-Nitrate-Catalyzed Oxidative Esterification of Aldehydes and Alcohols with <i>N</i> -Hydroxyphthalimide: Efficient Synthesis of <i>N</i> -Hydroxyimide Esters
  作者：Xiaohe Xu、Jian Sun、Yuyan Lin、Jingya Cheng、Pingping Li、Xiaoying Jiang、Renren Bai、Yuanyuan Xie

  DOI：10.1002/ejoc.201701411

  日期：2017.12.22

  An Fe(NO3)3*9H2O-catalyzed cross-dehydrogenative coupling reaction between N-hydroxyphthalimide (NHPI) or N-hydroxysuccinimide (NHSI) and aldehydes or alcohols in the air has been described. This transformation provided an efficient approach to prepare N-hydroxyimide ester derivatives with wide substrate scope in moderate to excellent yields.

  已经描述了 Fe(NO3)3*9H2O 催化的 N-羟基邻苯二甲酰亚胺 (NHPI) 或 N-羟基琥珀酰亚胺 (NHSI) 与空气中的醛或醇之间的交叉脱氢偶联反应。这种转化为制备具有广泛底物范围的 N-羟基酰亚胺酯衍生物提供了一种有效的方法，产率中等至极好。
• Metal-free intermolecular C–O cross-coupling reactions: synthesis of N-hydroxyimide esters
  作者：Yunhe Lv、Kai Sun、Weiya Pu、Shukuan Mao、Gang Li、Jiejie Niu、Qian Chen、Tingting Wang

  DOI：10.1039/c6ra22653a

  日期：——

  Selectfluor-mediated intermolecular C–O cross coupling reaction for the synthesis of N-hydroxyimide esters was developed for the first time. The reaction is applicable to the coupling of readily available aryl and alkyl aldehydes with N-hydroxyphthalimide (NHPI) and N-hydroxysuccinimide (NHSI). The resulting active esters can be directly converted into amides in one pot.

  首次开发了Selectfluor介导的分子间C–O交叉偶联反应，用于合成N-羟基酰亚胺酯。该反应适用于容易获得的芳基和烷基醛与N-羟基邻苯二甲酰亚胺（NHPI）和N-羟基琥珀酰亚胺（NHSI）的偶联。可以在一锅中将所得的活性酯直接转化为酰胺。
• Tripeptide derivatives
  申请人：Dainippon Pharmaceutical Co., Ltd.

  公开号：US04826814A1

  公开（公告）日：1989-05-02

  There are provided tripeptide compounds represented by the following formula ##STR1## wherein R.sub.1 represents a C.sub.1-10 alkyl group, a C.sub.4-7 cycloalkyl or C.sub.5-7 cycloalkyl-lower alkyl group, a phenyl or phenyl-lower alkyl group in which the benzene ring may optionally be substituted by a substituent selected from halogen, lower alkyl, lower alkoxy, phenyl, methylenedioxy, ethylenedioxy, amino, di(lower alkyl)amino and hydroxy, a naphthyl or naphthyl-lower alkyl group in which the naphthalene ring may optionally be substituted by a substituent selected from halogen, lower alkyl, lower alkoxy and hydroxy, a heterocyclic or heterocyclic-lower alkyl group in which the heterocycle is a saturated or unsaturated 5- or 6-membered ring containing a nitrogen, oxygen or sulfur atom as the hetero atom, and may optionally be substituted by a substituent selected from halogen, lower alkyl, lower alkoxy, amino, di(lower alkyl)amino, hydroxy, oxo and saturated 5- or 6-membered nitrogen-containing heterocyclic group, and further may optionally be fused to a benzene ring, or an imidazolylvinyl group; R.sub.2 represents a hydrogen atom, a C.sub.1-10 alkyl group or a benzyl group; R.sub.3 represents a group of the formula ##STR2## represents a benzene, cyclopentane or cyclohexane ring, R.sub.4 represents a hydrogen atom, a C.sub.1-10 alkyl group or a benzyl group, p is 0 or 1, q is 1, 2, or 3, and X represents a phenyl group which may optionally be substituted by a substituent selected from halogen, lower alkoxy and hydroxy, a C.sub.4-8 cycloalkyl group, or a C.sub.5-7 cycloalkyl group which is fused to a benzene, and Y represents a hydrogen atom or a lower alkyl group, or X and Y, together with the nitrogen and carbon atoms to which they are bonded, forms a 5- or 6-membered heterocycle which may contain a nitrogen, oxygen or sulfur atom, W represents a single bond, --O-- or --NH--, T represents a single bond, ##STR3## and m is 2 or 3, or salts thereof and processes for production thereof. The compounds are useful as antihypertensive agents.

  提供的三肽化合物的化学式如下所示：其中R.sub.1代表C.sub.1-10烷基基团、C.sub.4-7环烷基或C.sub.5-7环烷基-低烷基基团、苯基或苯基-低烷基基团，其中苯环可能被卤素、低烷基、低烷氧基、苯基、亚甲二氧基、乙二氧基、氨基、二(低烷基)氨基和羟基等取代基取代；萘基或萘基-低烷基基团，其中萘环可能被卤素、低烷基、低烷氧基和羟基等取代基取代；杂环或杂环-低烷基基团，其中杂环是饱和或不饱和的含氮、氧或硫原子的5-或6-成员环，可能被卤素、低烷基、低烷氧基、氨基、二(低烷基)氨基、羟基、氧代和饱和的含氮5-或6-成员环取代基取代，并且可能与苯环融合，或者是咪唑乙烯基团；R.sub.2代表氢原子、C.sub.1-10烷基基团或苄基团；R.sub.3代表下式中的基团##STR2## 代表苯、环戊烷或环己烷环，R.sub.4代表氢原子、C.sub.1-10烷基基团或苄基团，p为0或1，q为1、2或3，X代表苯基，可能被卤素、低烷氧基和羟基等取代基取代，C.sub.4-8环烷基，或与苯融合的C.sub.5-7环烷基，Y代表氢原子或低烷基基团，或X和Y连同它们结合的氮和碳原子形成一个含氮、氧或硫原子的5-或6-成员杂环，W代表单键，-O-或-NH-，T代表单键，##STR3## m为2或3，或其盐和生产方法。这些化合物可用作降压药。
• General Method for the Preparation of Active Esters by Palladium-Catalyzed Alkoxycarbonylation of Aryl Bromides
  作者：Angelina M. de Almeida、Thomas L. Andersen、Anders T. Lindhardt、Mauro V. de Almeida、Troels Skrydstrup

  DOI：10.1021/jo5025464

  日期：2015.2.6

  A useful method was developed for the synthesis of active esters by palladium-catalyzed alkoxycarbonylation of (hetero)aromatic bromides. The protocol was general for a range of oxygen nucleophiles including N-hydroxysuccinimide (NHS), pentafluorophenol (PFP), hexafluoroisopropyl alcohol (HFP), 4-nitrophenol, and N-hydroxyphthalimide. A high functional group tolerance was displayed, and several active esters were prepared with good to excellent isolated yields. The protocol was extended to access an important synthetic precursor to the HIV-protease inhibitor, saquinavir, by formation of an NHS ester followed by acyl substitution.