N-(3,5-二甲基苯基)-2-(4-羟基苯基)乙酰胺 | 131179-77-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(3,5-二甲基苯基)-2-(4-羟基苯基)乙酰胺
• 英文名称: N-(3,5-dimethylphenyl)-4-hydroxyphenylacetamide
• 英文别名: 4-<<(3,5-dimethylanilino)carbonyl>methyl>phenol；N-(3,5-dimethylphenyl)-2-(4-hydroxyphenyl)acetamide；4-[[(3,5-dimethylanilino)carbonyl]methyl]phenol；N-(3,5-dimethylphenyl)-4-hydroxybenzylamide
• CAS: 131179-77-6
• 化学式: C₁₆H₁₇NO₂
• 分子量: 255.316
• InChiKey: ZTSYSJBCQOANFS-UHFFFAOYSA-N

物化性质

• 熔点：
  173-176°C
• 沸点：
  483.7±33.0 °C(Predicted)
• 密度：
  1.191±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2924299090
• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  N-(3,5-二甲基苯基)-2-(4-羟基苯基)乙酰胺 在 N-甲基吗啉 、 sodium hydroxide 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 methyl (2S)-2-[[1-[4-[2-(3,5-dimethylanilino)-2-oxoethyl]phenoxy]cyclopentanecarbonyl]amino]propanoate
  参考文献：
  名称：

  Synthesis and X-ray Studies of Chiral Allosteric Modifiers of Hemoglobin

  摘要：

  This study was designed to investigate the effect of chirality on the allosteric activity of a series of Hb allosteric modifiers. The chiral analogues were based on the lead compound (4), JP7, {1-[4-(((3,5-dimethylanilino)carbonyl)methyl)phenoxy]cyclopentanecarboxylic acid} with different D- and L-amino acids conjugated to the JP7 acid moiety. The D-isomers were the most potent in vitro effectors in Hb solutions as well as with whole blood. In general, this study demonstrated that the chirality of extended amino acid side chains in JP7 conjugates plays an important role in observed degree of allosteric activity. The binding site interactions for four analogues were determined by single crystallographic diffraction studies. Conclusions show that the chiral configuration of some of the D-isomers enable the effectors to bind with a greater number of interactions with the protein residues. D- and L-isomers with equivalent or near equivalent allosteric activity did not show any significant differences or interactions between their amino acid side chains and the protein. The most potent effectors, in vitro, were compounds 15 and 19, D-isomers of leucine and phenylalanine, respectively. Compounds 21, 22, 30, and 32 were more potent in vitro in Hb solutions than JP7.

  DOI：

  10.1021/jm010358l
• 作为产物：
  描述：

  对羟基苯乙酸 在 氯化亚砜 作用下， 以 xylene 为溶剂， 反应 3.5h， 生成 N-(3,5-二甲基苯基)-2-(4-羟基苯基)乙酰胺
  参考文献：
  名称：

  使用液相色谱-大气压电离-串联质谱法对依法洛昔洛（RSR13）进行质谱表征，并将其实施到掺杂控制中。

  摘要：

  根据世界反兴奋剂机构（WADA），在体育运动中禁止使用Efaproxiral（2- [4-[[（（3,5-二甲基苯胺基羰基）甲基]苯氧基] -2-甲基丙酸。使用电喷雾电离（ESI）和串联质谱法，通过使用新型线性离子阱-轨道阱混合质谱仪- -在正电离和负电离模式下。在两种电荷状态下，消除2-甲基丙烯酸（-86 u）是主要的裂解过程。负离子化和碰撞诱导解离（CID）导致二氧化碳的额外释放（-44 u），正离子化导致甲酸的损失（-46 u）。

  DOI：

  10.1002/jms.993

文献信息

• Allosteric modifiers of hemoglobin. 1. Design, synthesis, testing, and structure-allosteric activity relationship of novel hemoglobin oxygen affinity decreasing agents
  作者：Ramnarayan S. Randad、Mona A. Mahran、Ahmed S. Mehanna、Donald J. Abraham

  DOI：10.1021/jm00106a041

  日期：1991.2

  included 4-[[(aryloyl)amino]methyl]phenoxy, 4-(arylacetamido)phenoxy, and 4-[[(arylamino)carbonyl]methyl]phenoxy. A total of 20 compounds were synthesized and tested. Structure-activity relationships are presented. Several of the new compounds were found to be strong allosteric effectors of hemoglobin. The two most active compounds are 2-[4-[[(3,5-dichloroanilino)carbonyl]-methyl]phenoxy]- 2-methylpropionic

  制备了2-（芳氧基）-2-甲基丙酸的三个异构体系列，并研究了它们降低人血红蛋白A的氧亲和力的能力。异构体芳氧基包括4-[[[（芳基）氨基]甲基]苯氧基，4 -（芳基乙酰氨基）苯氧基和4-[[[（芳基氨基）羰基]甲基]苯氧基。总共合成和测试了20种化合物。提出了构效关系。发现几种新化合物是血红蛋白的强变构效应物。两种最具活性的化合物是2- [4-[[（（3,5-二氯苯胺基）羰基]-甲基]苯氧基] -2-甲基丙酸和相应的3,5-二甲基衍生物。后两种化合物已在同一试验中与其他已知的强变构效应子进行了比较，并显示出更高的活性。与全血一起孵育时，这两种化合物的氧平衡曲线也都向右移动。新化合物可能在需要或受益于氧气供应逆转的临床或生物学领域（例如，缺血，中风，肿瘤放疗，储血，血液替代品等）中可能引起关注。它们在结构上还与几种市售的抗血脂药有关。
• Selective Phenol Alkylation: An Improved Preparation of Efaproxiral
  作者：Joanne E. Anderson、Roman Davis、Russ N. Fitzgerald、Jannine M. Haberman

  DOI：10.1080/00397910600636527

  日期：2006.6

  Abstract An improved, two‐step synthesis of efaproxiral, used in breast cancer therapy, is described, utilizing inexpensive commodity chemicals for starting materials. Selective amide formation and O‐alkylation in the presence of multireactive functional groups is demonstrated, thus avoiding protection/deprotection steps.

  摘要描述了一种改进的两步法合成，用于乳腺癌治疗，使用廉价的商品化学品作为起始材料。证明了在多反应性官能团存在下选择性酰胺形成和 O-烷基化，从而避免了保护/脱保护步骤。
• Clickable coupling of carboxylic acids and amines at room temperature mediated by SO₂F₂: a significant breakthrough for the construction of amides and peptide linkages
  作者：Shi-Meng Wang、Chuang Zhao、Xu Zhang、Hua-Li Qin

  DOI：10.1039/c9ob00699k

  日期：——

  carboxylic acids with amines was developed for the synthesis of a broad scope of amides in a simple, mild, highly efficient, robust and practical manner (>110 examples, >90% yields in most cases). The direct click reactions of acids and amines on a gram scale are also demonstrated using an extremely easy work-up and purification process of washing with 1 M aqueous HCl to provide the desired amides in

  酰胺键和肽键的构建是所有生命过程和有机合成中最基本的转变之一。结构无处不在的酰胺基序的合成对于许多重要分子（如肽，蛋白质，生物碱，药剂，聚合物，配体和农用化学品）的组装至关重要。开发了一种SO2F2介导的羧酸与胺的直接可点击偶合方法，以简单，温和，高效，稳健和实用的方式合成各种酰胺（> 110例，大多数情况下> 90％的收率） ）。
• MCF-supported boronic acids as efficient catalysts for direct amide condensation of carboxylic acids and amines
  作者：Liuqun Gu、Jaehong Lim、Jian Liang Cheong、Su Seong Lee

  DOI：10.1039/c4cc01148a

  日期：——

  For efficient direct amide condensations, a new class of catalysts are developed by immobilizing boronic acids on mesocellular siliceous foam. Associated with their large pores, the microenvironments surrounding the immobilized active species greatly influence the catalytic activity. The fluoroalkyl moieties on the silica surface significantly enhance the catalytic performance along with easy recovery

  为了有效地直接进行酰胺缩合，通过将硼酸固定在介孔硅质泡沫上，开发了新型的催化剂。与它们的大孔相关联，固定化活性物质周围的微环境极大地影响了催化活性。二氧化硅表面上的氟代烷基部分显着增强了催化性能，并易于回收和再利用。该方法提出了优化各种类型的二氧化硅负载的催化剂的潜在方法。
• Insights into Fast Amide Couplings in Aqueous Nanomicelles
  作者：Sudripet Sharma、Gaganpreet Kaur、Sachin Handa

  DOI：10.1021/acs.oprd.1c00203

  日期：2021.8.20

  has both lipophilic and hydrophilic regions, causing self-aggregation (also called nanoparticle formation) in an aqueous medium containing PS-750-M amphiphile. Kinetic and proton nuclear magnetic resonance studies were used to probe the effect of different organic bases on the potential nanoparticle formation of EDC•HCl. It also reveals why the pyridine base works better under micellar conditions. The

  1-Ethyl-3-(3-(二甲氨基)丙基)-碳二亚胺 (EDC•HCl) 具有亲脂性和亲水性区域，在含有 PS-750-M 两亲物的水性介质中引起自聚集（也称为纳米颗粒形成）。动力学和质子核磁共振研究用于探测不同有机碱对 EDC•HCl 潜在纳米颗粒形成的影响。它还揭示了为什么吡啶碱在胶束条件下效果更好。该方法在生物活性分子的多克规模合成上进行了检查，其中在没有产物差向异构化的情况下获得了优异的反应收率，同时保持了更短的反应时间。