3-氯-N-(4-羟基苯基)丙酰胺 | 19314-10-4

• 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: 3-氯-N-(4-羟基苯基)丙酰胺
• 中文别名: 3-氯-N-(4-羟基苯基)-丙酰胺
• 英文名称: β-Chlor-propionsaeure-(4-hydroxy-anilid)
• 英文别名: 3-chloro-propionic acid-(4-hydroxy-anilide)；3-Chlor-propionsaeure-(4-hydroxy-anilid)；β-Chlor-propionsaeure-(4-oxy-anilid)；3-chloro-N-(4-hydroxyphenyl)propanamide
• CAS: 19314-10-4
• 化学式: C₉H₁₀ClNO₂
• 分子量: 199.637
• InChiKey: QMHVIXPPSYYGJY-UHFFFAOYSA-N

物化性质

• 沸点：
  433.8±30.0 °C(Predicted)
• 密度：
  1.341±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2924299090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  3-氯-N-(4-羟基苯基)丙酰胺 在 咪唑 、 三氯化铝 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 6-(tert-butyldimethylsilanyloxy)-3,4-dihydroquinolin-2(1H)-one
  参考文献：
  名称：

  Synthesis, Biological Activity, and Three-Dimensional Quantitative Structure−Activity Relationship Model for a Series of Benzo[c]quinolizin-3-ones, Nonsteroidal Inhibitors of Human Steroid 5α-Reductase 1

  摘要：

  New 5alpha-reductase 1 (5alphaR-1) inhibitors were designed to complete a consistent set of analogues suitable for a 3D QSAR study. These compounds were synthesized by a modification of the aza-Robinson annulation, further functionalized by Pd-catalyzed cross-coupling processes, and were tested with human 5alphaR-1 expressed in Chinese hamster ovary 1827 cells. It turned out that the potency of the resulting inhibitors was strongly dependent on the type of substitution at the 8 position, with the IC50 values ranging from 8.1 to 1050 nM. The construction of this homogeneous set of molecules allowed a 3D QSAR study. In particular, comparative molecular field analysis (CoMFA) was used to correlate the potency of the inhibitors with their physicochemical features. Highly accurate evaluations of the atomic point charges were carried out by means of quantum chemical calculations at the DFT/B3LYP level of theory followed by the RESP fitting procedure. It turned out that increasing the reliability of electrostatic parameters greatly affected the statistical results of the QSAR analysis. The 3D QSAR model proposed could be very useful in the further development of 5alphaR-1 inhibitors, which are suitable candidates to be evaluated as drugs in the treatment of 5alphaR-1 related diseases such as acne and alopecia in men and hirsutism in women.

  DOI：

  10.1021/jm031131o
• 作为产物：
  描述：

  对氨基苯酚 、 3-氯丙酰氯 以 二氯甲烷 、 碳酸氢钠 为溶剂， 反应 3.08h， 以to afford 3-chloro-N-(4-hydroxyphenyl)propanamide的产率得到3-氯-N-(4-羟基苯基)丙酰胺
  参考文献：
  名称：

  2-[2--1H-Pyrrolo[2,3-D]Pyrimidin-4-YL)Amino] Benzamide Derivatives As IGF-1R Inhibitors For The Treatment Of Cancer

  摘要：

  式(I)所示的新型吡咯吡咪啉及其药学上可接受的衍生物。这些化合物在抑制IGF-1R方面是有用的。

  公开号：

  US20100204196A1

文献信息

• [EN] 2- [ (2-{PHENYLAMINO}-1H-PYRROLO [2, 3-D] PYRIMIDIN-4-YL) AMINO] BENZAMIDE DERIVATIVES AS IGF-1R INHIBITORS FOR THE TREATMENT OF CANCER<br/>[FR] DÉRIVÉS DE 2-[(2-{PHÉNYLAMINO}-1H-PYRROLO[2,3-D]PYRIMIDIN-4-YL)AMINO]BENZAMIDE EN TANT QU'INHIBITEUR D'IGF-1R POUR LE TRAITEMENT DU CANCER
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2009020990A1

  公开（公告）日：2009-02-12

  Novel pyrrolopyrimidines as shown in formula (I) and pharmaceutically acceptable derivatives thereof. The compounds are useful in the inhibition of IGF-1R.

  新型吡咯吡嘧啶如公式(I)所示，及其药用可接受的衍生物。这些化合物在抑制IGF-1R方面是有用的。
• Inhibitors of the Human Aldosterone Sythase CYP11B2
  申请人：Hartmann Rolf W.

  公开号：US20110112067A1

  公开（公告）日：2011-05-12

  The invention provides compounds of the general formula (I) which are inhibitors of the human aldosterone synthase, and also pharmaceutical compositions containing these compounds, and a method of treating of hyperaldosteronism and/or disorders or diseases that are mediated by 11β-hydroxylase (CYP11B1) with these compounds.

  该发明提供了一般式(I)的化合物，这些化合物是人类醛固酮合成酶的抑制剂，还包括含有这些化合物的药物组合物，以及使用这些化合物治疗高醛固酮症和/或由11β-羟化酶（CYP11B1）介导的疾病或疾病的方法。
• α-Glucosidase Inhibitory Constituents from Acanthopanax senticosus Harm Leaves
  作者：Zhi-Bin Wang、Hai Jiang、Yong-Gang Xia、Bing-You Yang、Hai-Xue Kuang

  DOI：10.3390/molecules17066269

  日期：——

  A new triterpene glycoside, 3-O-[(α-L-rhamnopyranosyl)(1→2)]-[β-D-glucuronopyranosyl-6-O-methyl ester]-olean-12-ene-28-olic acid (1) and a new indole alkaloid, 5-methoxy-2-oxoindolin-3-acetic acid methyl ester (5) were isolated from the leaves of Acanthopanax senticosus Harms along with six known compounds. The structures of the new compounds were determined by means of 2D-NMR experiments and chemical

  一种新的三萜糖苷，3-O-[(α-L-rhamnopyranosyl)(1→2)]-[β-D-glucuronopyranosyl-6-O-methylester]-olean-12-ene-28-olic acid ( 1) 和一种新的吲哚生物碱 5-甲氧基-2-氧代吲哚啉-3-乙酸甲酯 (5) 与六种已知化合物一起从刺五加的叶子中分离出来。通过二维核磁共振实验和化学方法确定了新化合物的结构。评价了所有分离的化合物的糖苷酶抑制活性，化合物 6 显示出显着的 α-葡萄糖苷酶抑制活性。
• Processes for preparing 6-hydroxy-3,4-dihydroquinolinone, cilostazol and N-(4-methoxyphenyl)-3-chloropropionamide
  申请人：——

  公开号：US20020032333A1

  公开（公告）日：2002-03-14

  A process for preparing 6-hydroxy-3,4-dihydroquinolinone by intramolecular Friedel-Crafts alkylation of N-(4-methoxyphenyl)-3-chloropropionamide in which an equivalent of N-(4-methoxyphenyl)-3-chloropropionamide is contacted with a Lewis acid in DMSO or a high boiling amide or amine at an elevated temperature of from about 150° C. to about 220° C. is provided. The process produces 6-HQ in high yield and a high state of purity such that it may be used in subsequent reactions toward the preparation of cilostazol without intermediate purification. A process for preparing cilostazol from 6-hydroxy-3,4-dihydroquinolinone prepared by the process and improved processes for preparing N-(4-methoxyphenyl)-3-chloropropionamide are also provided.

  提供一种制备6-羟基-3,4-二氢喹啉酮的方法，通过N-(4-甲氧基苯基)-3-氯丙酰胺的分子内Friedel-Crafts烷基化反应，在其中，将N-(4-甲氧基苯基)-3-氯丙酰胺的当量与DMSO中的Lewis酸或高沸点酰胺或胺在约150°C至约220°C的升温条件下接触。该方法高产率地生产6-HQ，并具有高纯度，可用于制备环噻唑胺而无需中间纯化。还提供了一种从该方法制备的6-羟基-3,4-二氢喹啉酮制备环噻唑胺的方法，以及改进的制备N-(4-甲氧基苯基)-3-氯丙酰胺的方法。
• [EN] PROCESSES FOR PREPARING 6-HYDROXY-3,4-DIHYDROQUINOLINONE, CILOSTAZOL AND N-(4-METHOXYPHENYL)-3-CHLOROPROPIONAMIDE<br/>[FR] PROCEDES DE PREPARATION DE 6-HYDROXY-3,4-DIHYDROQUINOLINONE, DE CILOSTAZOL ET DE N-(4-METHOXYPHENYL)-3-CHLOROPROPIONAMIDE
  申请人：TEVA PHARMA

  公开号：WO2001070697A1

  公开（公告）日：2001-09-27

  A process for preparing 6-hydroxy-3,4-dihydroquinolinone by intramolecular Friedel-Crafts alkylation of N-(4-methoxyphenyl)-3-chloropropionamide in which an equivalent of N-(4-methoxyphenyl)-3-chloropropionamide is contacted with a Lewis acid in DMSO or a high boiling amide or amine at an elevated temperature of from about 150 °C to about 220 °C is provided. The process produces 6-HQ in high yield and a high state of purity such that it may be used in subsequent reactions toward the preparation of cilostazol without intermediate purification. A process for preparing cilostazol from 6-hydroxy-3,4-dihydroquinolinone prepared by the process and improved processes for preparing N-(4-methoxyphenyl)-3-chloropropionamide are also provided.

  提供一种制备6-羟基-3,4-二氢喹啉酮的方法，该方法通过N-(4-甲氧基苯基)-3-氯丙酰胺的分子内Friedel-Crafts烷基化反应，其中等量的N-(4-甲氧基苯基)-3-氯丙酰胺在DMSO或高沸点酰胺或胺的高温条件下（约150℃至220℃）与路易斯酸接触。该方法产生高产率和高纯度的6-HQ，可以在不经过中间纯化的情况下用于制备cilostazol的后续反应。此外，还提供了一种从该方法制备的6-羟基-3,4-二氢喹啉酮制备cilostazol的方法和改进的制备N-(4-甲氧基苯基)-3-氯丙酰胺的方法。