1-环丙基-2-(4-氟苯基)乙酮 | 1071842-61-9

• 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: 1-环丙基-2-(4-氟苯基)乙酮
• 中文别名: 环丙基4-氟苄基酮
• 英文名称: 1-cyclopropyl-2-(4-fluorophenyl)ethanone
• CAS: 1071842-61-9
• 化学式: C₁₁H₁₁FO
• 分子量: 178.206
• InChiKey: YMSQEGGMZUPCFH-UHFFFAOYSA-N

物化性质

• 熔点：
  43-45°C
• 溶解度：
  二氯甲烷、DMSO、乙酸乙酯、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-环丙基-2-(4-氟苯基)乙酮 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 10.5h， 生成 4-cyclopropyl-5-(4-fluorophenyl)pyrimidin-2-amine
  参考文献：
  名称：

  Small Molecule that Reverses Dexamethasone Resistance in T-cell Acute Lymphoblastic Leukemia (T-ALL)

  摘要：

  Glucocorticoids are one of the most utilized and effective therapies in treating T-cell acute lymphoblastic leukemia. However, patients often develop resistance to glucocorticoids, rendering these therapies ineffective. We screened 9517 compounds, selected for their lead-like properties, chosen from among 3 372 615 compounds, against a dexamethasone-resistant T-ALL cell line to identify small molecules that reverse glucocorticoid resistance. We synthesized analogues of the most effective compound, termed J9, from the screen in order to define the scaffold's structure activity relationship. Active compounds restored sensitivity to glucocorticoids through upregulation of the glucocorticoid receptor. This compound and mechanism may provide a strategy for overcoming glucocorticoid resistance in patients with T-ALL.

  DOI：

  10.1021/ml500044g
• 作为产物：
  描述：

  环丙基溴化镁 、 对氟苯乙酰氯 在 copper(I) bromide 作用下， 以 四氢呋喃 为溶剂， 反应 4.67h， 生成 1-环丙基-2-(4-氟苯基)乙酮
  参考文献：
  名称：

  Small Molecule that Reverses Dexamethasone Resistance in T-cell Acute Lymphoblastic Leukemia (T-ALL)

  摘要：

  Glucocorticoids are one of the most utilized and effective therapies in treating T-cell acute lymphoblastic leukemia. However, patients often develop resistance to glucocorticoids, rendering these therapies ineffective. We screened 9517 compounds, selected for their lead-like properties, chosen from among 3 372 615 compounds, against a dexamethasone-resistant T-ALL cell line to identify small molecules that reverse glucocorticoid resistance. We synthesized analogues of the most effective compound, termed J9, from the screen in order to define the scaffold's structure activity relationship. Active compounds restored sensitivity to glucocorticoids through upregulation of the glucocorticoid receptor. This compound and mechanism may provide a strategy for overcoming glucocorticoid resistance in patients with T-ALL.

  DOI：

  10.1021/ml500044g

文献信息

• Antiarrhythmic imidazoles
  申请人：Schering A.G.

  公开号：US04689341A1

  公开（公告）日：1987-08-25

  The imidazolium salts described are useful as antiarrhythmic agents. A method of treating arrhythmia by increasing the refractoriness of cardiac tissue is provided as well as pharmaceutical formulations containing such imidazolium salts.

  所描述的咪唑盐可用作抗心律失常剂。还提供了一种通过增加心脏组织的不应期来治疗心律失常的方法，以及含有此类咪唑盐的制药配方。
• Antiarrhythmic imidazoliums
  申请人：Schering A.G.

  公开号：US04581370A1

  公开（公告）日：1986-04-08

  The imidazolium salts described are useful as antiarrhythmic agents. A method of treating arrhythmia by increasing the refractoriness of cardiac tissue is provided as well as pharmaceutical formulations containing such imidazolium salts. The compounds are described by the following formula: ##STR1##

  所述的咪唑盐可用作抗心律失常药物。提供了一种通过增加心脏组织的不应期来治疗心律失常的方法，以及含有这种咪唑盐的制药配方。该化合物由以下公式描述：##STR1##
• Imidazolium salts, intermediates thereto and their use
  申请人：SCHERING AKTIENGESELLSCHAFT

  公开号：EP0131302A2

  公开（公告）日：1985-01-16

  The imidazolium salts described are useful as antiarrhythmic agents. A method of treating arrhythmia by increasing the refractoriness of cardiac tissue is provided as well as pharmaceutical formulations containing such imidazolium salts.

  所述咪唑盐可用作抗心律失常药物。本文提供了一种通过增加心脏组织的折射性来治疗心律失常的方法，以及含有此类咪唑鎓盐的药物制剂。
• Lewis acid-mediated reactions of 1-cyclopropyl-2-arylethanone derivatives with diethyl 2-oxomalonate and ethyl 2-oxoacetate
  作者：Xiang-Ying Tang、Min Shi

  DOI：10.1016/j.tet.2009.09.003

  日期：2009.11

  TMSOTf-mediated reactions of 2-aryl-1-(1-phenylcyclopropyl)ethanones 1 with diethyl 2-oxomalonate 2 afford a novel method for the synthesis of spiro-gamma-lactone derivatives 3 in good to excellent yields via a sequential reaction involving a nucleophilic ring-opening reaction of the cyclopropane by H2O, an aldol-type reaction and a cyclic transesterification mediated by Lewis acid. On the other hand, we found that TMSOTf-mediated reactions of 1-cyclopropyl-2-arylethanones 1 with ethyl 2-oxoacetate 4 could also provide the corresponding spiro-gamma-lactone derivatives 5 in moderate yields along with another spiro-gamma-lactone derivatives 6 derived from the reaction of 1 with two molecules of ethyl 2-oxcracetate. The plausible reaction mechanisms have also been provided on the basis of control experiments. (c) 2009 Elsevier Ltd. All rights reserved.
• Vilsmeier−Haack Reaction of 1-Cyclopropyl-2-arylethanones
  作者：Xiang-Ying Tang、Min Shi

  DOI：10.1021/jo801492k

  日期：2008.11.7

  A convenient and efficient method to synthesize 3-(2-chloroethyl)-5-aryl-4H-pyran-4-ones 2 and 2-chloro-3-(2-chloroethyl)-1-naphthaldehydes 3 in moderate to good yields was developed via the Vilsmeier-Haack reaction of readily available 1-cyclopropyl-2-arylethanones 1 at different temperature. This reaction proceeds via sequential enolization, ring opening, haloformylation, and intramolecular nucleophilic cyclization or Friedel-Crafts alkylation reactions to produce 2 or 3.