N-(乙酰基)-4-氨基苯乙醛 | 1085309-04-1

• 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-(乙酰基)-4-氨基苯乙醛
• 英文名称: (p-acetylamino)phenylacetaldehyde
• 英文别名: N-[4-(2-oxoethyl)phenyl]acetamide
• CAS: 1085309-04-1
• 化学式: C₁₀H₁₁NO₂
• 分子量: 177.203
• InChiKey: HGCUIKKLQISTFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(乙酰基)-4-氨基苯乙醛 在 sodium hydride 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 5-(4-acetylamino-benzyl)-3-methyl-3,4-dihydro-2H-pyrazole-3-carboxylic acid (4-chloro-3-trifluoromethyl-phenyl)-amide
  参考文献：
  名称：

  Design, Synthesis, and in Vivo SAR of a Novel Series of Pyrazolines as Potent Selective Androgen Receptor Modulators

  摘要：

  A novel series of pyrazolines 2 have been designed, synthesized, and evaluated by in vivo screening as tissue-selective androgen receptor modulators (SARMs). Structure- activity relationships (SAR) were investigated at the R-1 to R-6 positions as well as the core pyrazoline ring and the anilide linker. Overall, strong electron-withdrawing groups at the RI and 2 positions and a small group at the R1 and RI position are optimal for AR agonist activity. The (S)-isomer of 7c exhibits more potent AR agonist activity than the corresponding (R)-isomer. (S)-7c exhibited an overall partial androgenic effect but full anabolic effect via oral administration in castrated rats. It demonstrated a noticeable antiandrogenic effect on prostate in intact rats with endogenous testosterone. Thus, (S)-7c is a tissue-selective nonsteroidal androgen receptor modulator with agonist activity on muscle and mixed agonist and antagonist activity on prostate.

  DOI：

  10.1021/jm0613976
• 作为产物：
  描述：

  N-[4-(2-羟基乙基)苯基]乙酰胺 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 生成 N-(乙酰基)-4-氨基苯乙醛
  参考文献：
  名称：

  用于黑色素瘤的咪唑和咪唑啉类似物的合成和抗增殖活性。

  摘要：

  我们以前曾报道过取代的 2-芳基-噻唑烷-4-羧酸酰胺作为黑色素瘤的有效和选择性抗增殖剂。为了了解噻唑烷环的重要性并减少与两个手性中心相关的潜在并发症，我们通过修改该环设计并合成了多组新的类似物。这些新的类似物在两种黑色素瘤细胞系和成纤维细胞（阴性对照）中进行了测试。与含有噻唑烷环的旧类似物相比，这些新类似物总体上具有较低的效力，但其中一些类似物仍然具有非常好的选择性。这些结构-活性研究表明，噻唑烷环对于这些系列化合物的活性非常关键。

  DOI：

  10.1016/j.bmcl.2008.04.073
• 作为试剂：
  描述：

  (3aα,9bβ)-8-cyano-1,2,3,3a,4,9b-hexahydrochromeno[3,4-c]pyrrole 、 N-(乙酰基)-4-氨基苯乙醛 在 N-(乙酰基)-4-氨基苯乙醛 作用下， 生成 外消旋S33138
  参考文献：
  名称：

  Bioorg. Med. Chem. Lett. 1999, 9, 2059-2064

  摘要：

  DOI：

文献信息

• Metal-Free Dehydrogenative Diels–Alder Reactions of Prenyl Derivatives with Dienophiles via a Thermal Reversible Process
  作者：Wen-Lei Xu、Heng Zhang、Yu-Long Hu、Hui Yang、Jie Chen、Ling Zhou

  DOI：10.1021/acs.orglett.8b02469

  日期：2018.9.21

  An efficient dehydrogenative Diels–Alder reaction of prenyl derivatives with dienophiles has been developed. The reaction exhibits broad substrate scope and provides efficient access to cyclohexene derivatives with good to excellent yields. A reasonable mechanism involving a metal-free thermal reversible process is proposed.

  已开发出异戊二烯衍生物与亲二烯体的有效脱氢狄尔斯-阿尔德反应。该反应显示出广泛的底物范围，并以良好或优异的产率提供了有效地获得环己烯衍生物的途径。提出了涉及无金属热可逆过程的合理机理。
• Synthesis of Tetrahydroisoindolinones via a Metal‐Free Dehydrogenative Diels‐Alder Reaction
  作者：Wen‐Lei Xu、Lei Tang、Chen‐Yu Ge、Jie Chen、Ling Zhou

  DOI：10.1002/adsc.201801436

  日期：2019.5.14

  A metal‐free dehydrogenative Diels‐Alder reaction of substituted alkenes for the synthesis of tetrahydroisoindolinones has been exploited for the first time. This new method features functional group tolerance and broad substrate scope, providing an efficient access to biologically active tetrahydroisoindolinone skeletons with endo steroselectivity in good to excellent yields.

  首次开发了取代烯烃的无金属脱氢Diels-Alder反应用于合成四氢异吲哚满酮。这种新方法的特征官能团耐受性和广泛的底物范围，提供了一个有效的访问生物活性tetrahydroisoindolinone骨架与内切在良好立体选择性到优异的产率。
• Novel benzopyrano[3,4-c]pyrrole derivatives as potent and selective dopamine D3 receptor antagonists
  作者：Thierry Dubuffet、Adrian Newman-Tancredi、Didier Cussac、Valerie Audinot、Annie Loutz、Mark J. Millan、Gilbert Lavielle

  DOI：10.1016/s0960-894x(99)00312-1

  日期：1999.7

  A new series of benzopyrano[3,4-c]pyrrole derivatives were synthesized and evaluated for their interaction with dopamine D3 versus D2 receptors. Amongst these compounds, 4x (S 33084) was found to be a potent and selective dopamine D3 receptor antagonist.

  合成了一系列新的苯并吡喃并[3,4-c]吡咯衍生物，并评估了它们与多巴胺D3和D2受体的相互作用。在这些化合物中，发现4x（S 33084）是有效的选择性多巴胺D3受体拮抗剂。
• Method for treating a immunology-related disease
  申请人：Nishi Takahide

  公开号：US20090326038A1

  公开（公告）日：2009-12-31

  A method for treating an immunology-related disease. The method involves administering to a mammal in need thereof a pharmaceutically effective amount of an amino acid compound, a pharmacologically acceptable salt thereof or a pharmacologically acceptable ester thereof. The compound has the following formula: , wherein R 1 and R 2 are each hydrogen; R 3 is hydrogen; R 4 is C 1 -C 2 alkyl; n is 2; X is ═N-D, wherein D is hydrogen, C 1 -C 4 alkyl or phenyl; Y is ethylene, ethynylene, —CO—CH 2 or phenylene; Z is ethylene or trimethylene; R 5 is unsubstituted C 3 -C 10 cycloalkyl, unsubstituted C 3 -C 10 aryl, or C 3 -C 10 cycloalkyl or C 6 -C 10 aryl substituted with 1 to 3 substituents selected from the group consisting of halogen, lower alkyl, halogeno lower alkyl and lower alkoxy; and R 6 and R 7 are each hydrogen.

  一种治疗免疫相关疾病的方法。该方法涉及向需要治疗的哺乳动物中注射药物有效量的氨基酸化合物，其药理学上可接受的盐或其药理学上可接受的酯。该化合物具有以下式子：其中R1和R2均为氢；R3为氢；R4为C1-C2烷基；n为2；X为═N-D，其中D为氢、C1-C4烷基或苯基；Y为乙烯、乙炔基、—CO—CH2或苯基；Z为乙烯或三亚甲基；R5为未取代的C3-C10环烷基、未取代的C3-C10芳基或取代有1至3个卤素、低烷基、卤代低烷基和低烷氧基的C3-C10环烷基或C6-C10芳基；R6和R7均为氢。
• Algorithm-driven activity-directed expansion of a series of antibacterial quinazolinones
  作者：Daniel Francis、Sannia Farooque、Archie Meager、Didi Derks、Abbie Leggott、Stuart Warriner、Alex J. O'Neill、Adam Nelson

  DOI：10.1039/d2ob01404a

  日期：——

  Algorithms were harnessed in the design of arrays of photoredox-catalysed microscale reactions whose crude products were screened for antibacterial activity. The approach enabled expansion of a series of antibacterial agents.

  算法被利用在光还原催化微反应阵列的设计中，其粗制品被筛选用于抗菌活性。这种方法使得一系列抗菌剂的扩展成为可能。