N-(4-羟基-2-甲基苯基)乙酰胺 | 39495-15-3

• 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-(4-羟基-2-甲基苯基)乙酰胺
• 英文名称: 4-acetamido-3-methylphenol
• 英文别名: N-(4-hydroxy-2-methylphenyl)acetamide
• CAS: 39495-15-3
• 化学式: C₉H₁₁NO₂
• mdl: MFCD02660387
• 分子量: 165.192
• InChiKey: JPLCVGBNQZNQBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(4-羟基-2-甲基苯基)乙酰胺 在 盐酸 作用下， 生成 2-甲基-4-甲氧基苯胺
  参考文献：
  名称：

  Heidelberger; Jacobs, Journal of the American Chemical Society, 1919, vol. 41, p. 1457

  摘要：

  DOI：
• 作为产物：
  描述：

  4-硝基间甲苯酚 在 sodium hydroxide 、 sodium dithionite 、 水 作用下， 生成 N-(4-羟基-2-甲基苯基)乙酰胺
  参考文献：
  名称：

  MERCURY DERIVATIVES OF ACETYLAMINOCRESOLS¹

  摘要：

  DOI：

  10.1021/ja01373a031

文献信息

• Discovery of Adamantyl Ethanone Derivatives as Potent 11β-Hydroxysteroid Dehydrogenase Type 1 (11β-HSD1) Inhibitors
  作者：Xiangdong Su、Fabienne Pradaux-Caggiano、Mark P. Thomas、Michelle W. Y. Szeto、Heather A. Halem、Michael D. Culler、Nigel Vicker、Barry V. L. Potter

  DOI：10.1002/cmdc.201000081

  日期：——

  and cardiovascular diseases. A series of novel adamantyl ethanone compounds was identified as potent inhibitors of human 11β‐HSD1. The most active compounds identified (52, 62, 72, 92, 103 and 104) display potent inhibition of 11β‐HSD1 with IC50 values in the 50–70 nM range. Compound 72 also proved to be metabolically stable when incubated with human liver microsomes. Furthermore, compound 72 showed

  11β-羟基类固醇脱氢酶（11β-HSD）是调节糖皮质激素激素受体代谢的关键酶。用选择性抑制剂调节11β-HSD1型活性可对各种状况产生有益的影响，包括胰岛素抵抗，血脂异常和肥胖。通过调节11β-HSD1抑制组织特异性糖皮质激素的作用，对于代谢性疾病和心血管疾病构成了一种有希望的治疗方法。一系列新的金刚烷基乙酮化合物被鉴定为人类11β-HSD1的有效抑制剂。最活跃的鉴定（化合物52，62，72，92，103和104）显示11β-HSD1的有效抑制与IC 50值在50–70 n M范围内。与人肝微粒体一起孵育时，化合物72也被证明在代谢上是稳定的。此外，化合物72对人细胞色素P450酶的抑制活性非常弱，因此是体内研究的候选药物。人类11β-HSD1的公开X射线晶体结构的比较导致了对有效化合物的对接研究，揭示了这些分子如何与酶和辅因子相互作用。
• Synthesis and pharmacological evaluation of piperidine (piperazine)-amide substituted derivatives as multi-target antipsychotics
  作者：Ling Huang、Lanchang Gao、Xiaohua Zhang、Lei Yin、Jintao Hu、Ting Song、Yin Chen

  DOI：10.1016/j.bmcl.2020.127506

  日期：2020.10

  We report the optimisation of a series of novel amide-piperidine (piperazine) derivatives using the multiple ligand approach with dopamine and serotonin receptors. Of the derivatives, compound 11 exhibited high affinity for the D2, 5-HT1A, and 5-HT2A receptors, but low affinity for the 5-HT2C and histamine H1 receptors and human ether-a-go-go-related gene (hERG) channels. In vivo, compound 11 reduced

  我们报告了与多巴胺和5-羟色胺受体的多配体方法一系列新型酰胺-哌啶（哌嗪）衍生物的优化。在衍生物中，化合物11显示出高亲和力为d 2，5-HT 1A和5-HT 2A受体，但低亲和性对5-HT 2C和组胺H 2 1受体和人ether-A-GO-中间人相关基因（hERG）通道。体内化合物11即使在测试的最高剂量下，阿扑吗啡引起的攀爬，MK-801引起的活动过度和DOI引起的头部抽搐也没有明显的僵直。另外，它在CAR测试中表现出抑制作用。此外，在一个新颖的物体识别任务中，它显示了识别属性。因此，化合物11是有希望的候选多靶点抗精神病药。
• 4-Ethers of 3-amino-5-sulfamoylbenzoic acids
  申请人：Ciba-Geigy Corporation

  公开号：US03982018A1

  公开（公告）日：1976-09-21

  4-Phenylethers of 3-amino-5-sulfamoylbenzoic acids e.g. those of the formula ##SPC1## R = an araliphatic radical X = o or S R' = h, alkyl or aminophenyl Alkyl esters or salts thereof are diuretic agents.

  3-氨基-5-磺酰基苯甲酸的4-苯基醚，例如下列公式所示的化合物：##SPC1## R = 芳基烃基基团 X = o 或 S R' = h，烷基或氨基苯基 烷基酯或其盐是利尿剂。
• Aniline derivatives having herbicidal activity, their preparation and
  申请人：Sankyo Company, Limited

  公开号：US05736487A1

  公开（公告）日：1998-04-07

  Compounds of formula (I): ##STR1## (wherein: R.sup.1 is optionally substituted alkyl, cycloalkyl, optionally substituted alkoxy, or optionally substituted alkylthio; R.sup.2 is hydrogen, optionally substituted alkyl, cycloalkyl, optionally substituted alkenyl, optionally substituted alkynyl or a group of formula --YR.sup.7 ; R.sup.3 is optionally substituted alkyl, cycloalkyl, optionally substituted alkoxy group, optionally substituted alkenyl, optionally substituted alkynyl, halogen, nitro or a group of formula --COR.sup.8, wherein R.sup.8 is hydrogen, alkyl, cycloalkyl or alkoxy; R.sup.4 and R.sup.5 are each hydrogen atom or alkyl; R.sup.6 is optionally substituted alkyl, cycloalkyl, optionally substituted alkoxy group, optionally substituted alkenyl, optionally substituted alkynyl, halogen, nitro, or a group of formula --COR.sup.8, as defined above; A, Q and X are each oxygen or sulfur; Y is a group of formula --CO--, --COO--, --CH.sub.2 O--, --CH.sub.2 S--, --CH.sub.2 CH.sub.2 O--, --CH.sub.2 CH.sub.2 S--, --CH.sub.2 CO--, --CH.sub.2 COO--, --CH(Me)COO--, --CH.sub.2 CH.sub.2 CO--, --CH.sub.2 OCO--, CH.sub.2 OCOO-- and --CH.sub.2 CH.sub.2 OCO--; R.sup.7 is optionally substituted alkyl group, cycloalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted aralkyl, or an optionally substituted heterocycle; and m and n are each an integer from 0 to 4; and herbicidally acceptable addition salts thereof) are useful as herbicides.

  式(I)的化合物：##STR1##（其中：R.sup.1是可选择取代的烷基，环烷基，可选择取代的烷氧基，或可选择取代的烷硫基；R.sup.2是氢，可选择取代的烷基，环烷基，可选择取代的烯基，可选择取代的炔基或具有式--YR.sup.7的基团; R.sup.3是可选择取代的烷基，环烷基，可选择取代的烷氧基，可选择取代的烯基，可选择取代的炔基，卤素，硝基或具有式--COR.sup.8的基团，其中R.sup.8是氢，烷基，环烷基或烷氧基；R.sup.4和R.sup.5分别是氢原子或烷基；R.sup.6是可选择取代的烷基，环烷基，可选择取代的烷氧基，可选择取代的烯基，可选择取代的炔基，卤素，硝基，或具有上述定义的式--COR.sup.8的基团；A，Q和X分别是氧或硫；Y是具有式--CO--，--COO--，--CH.sub.2 O--，--CH.sub.2 S--，--CH.sub.2 CH.sub.2 O--，--CH.sub.2 CH.sub.2 S--，--CH.sub.2 CO--，--CH.sub.2 COO--，--CH(Me)COO--，--CH.sub.2 CH.sub.2 CO--，--CH.sub.2 OCO--，CH.sub.2 OCOO--和--CH.sub.2 CH.sub.2 OCO--的基团；R.sup.7是可选择取代的烷基，环烷基，可选择取代的烯基，可选择取代的炔基，可选择取代的芳基，可选择取代的芳基烷基，或可选择取代的杂环；m和n分别是0到4的整数；及其对应的除草剂可接受的加成盐）可用作除草剂。
• [EN] TRANSITION METAL COMPLEXES<br/>[FR] TRANSITION METAL COMPLEXES
  申请人：SHELL INT RESEARCH

  公开号：WO2005090371A1

  公开（公告）日：2005-09-29

  A transition metal complex which is a bis-arylimine pyridine MXn complex, comprising a bis-arylimine pyridine ligand having the formula (I), wherein R1-R5, R7-R9, R12 and R14 are each, independently, hydrogen, optionally substituted hydrocarbyl, an inert functional group, or any two of R1-R3 and R7-R9 vicinal to one another taken together may form a ring, and R6 is hydrogen, optionally substituted hydrocarbyl, an inert functional group, or taken together with R7 or R4 to form a ring, R10 is hydrogen, optionally substituted hydrocarbyl, an inert functional group, or taken together with R9 or R4 to form a ring, R11 is hydrogen, optionally substituted hydrocarbyl, an inert functional group, or taken together with R12 or R5 to form a ring, R15 is hydrogen, optionally substituted hydrocarbyl, an inert functional group, or taken together with R14 or R5 to form a ring, provided that R13 and at least one of R12 and R14 are independently selected from optionally substituted C1-C30 alkyl, optionally substituted C4-C30 alkyloxy, halogen and optionally substituted C5-C20 aryl, or R13 taken together with R12 or R14 form a ring, or R12 taken together with R11 form a ring and R14 taken together with R15 form a ring, and provided that at least one of R12, R13 and R14 is optionally substituted C4-C30 alkyloxy; M is a transition metal atom in particular selected from Ti, V, Cr, Mn, Fe, Co, Ni, Pd, Rh, Ru, Mo, Nb, Zr, Hf, Ta, W, Re, Os, Ir or Pt; n matches the formal oxidation state of the transition metal atom M; and X is halide, optionally substituted hydrocarbyl, alkoxide, amide, or hydride. The transition metal complexes of the present invention, their complexes with non-coordinating anions and catalyst systems containing such complexes have good solubility in non-polar media and chemically inert non-­polar solvents especially aromatic hydrocarbon solvents. The catalyst systems can be used for a wide range of (co­)oligomerization, polymerization and dimerization reactions.

  一种过渡金属配合物，为双芳胺吡啶MXn配合物，包括具有化学式(I)的双芳胺吡啶配体，其中R1-R5、R7-R9、R12和R14分别为独立的氢、可选择取代的烃基、惰性官能团，或R1-R3和R7-R9中的任意两个邻位取代基可以形成环，R6为氢、可选择取代的烃基、惰性官能团，或与R7或R4一起形成环，R10为氢、可选择取代的烃基、惰性官能团，或与R9或R4一起形成环，R11为氢、可选择取代的烃基、惰性官能团，或与R12或R5一起形成环，R15为氢、可选择取代的烃基、惰性官能团，或与R14或R5一起形成环，其中R13和至少一个R12和R14独立地选自可选择取代的C1-C30烷基、可选择取代的C4-C30烷氧基、卤素和可选择取代的C5-C20芳基，或R13与R12或R14一起形成环，或R12与R11一起形成环，R14与R15一起形成环，且至少一个R12、R13和R14为可选择取代的C4-C30烷氧基；M为过渡金属原子，特别选自Ti、V、Cr、Mn、Fe、Co、Ni、Pd、Rh、Ru、Mo、Nb、Zr、Hf、Ta、W、Re、Os、Ir或Pt；n与过渡金属原子M的形式氧化态相匹配；X为卤素、可选择取代的烃基、烷氧基、酰胺或氢化物。本发明的过渡金属配合物及其与非配位阴离子的复合物和含有此类配合物的催化系统在非极性介质和化学惰性非极性溶剂中具有良好的溶解性，特别是芳香烃类溶剂。该催化系统可用于广泛的(共)寡聚化、聚合和二聚化反应。