α-(3-Chlorophenoxy)acetophenone | 19514-06-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-(3-Chlorophenoxy)acetophenone
• 英文别名: ω-(3-Chlor-phenoxy)-acetophenon；5-Chloro-2-phenoxyacetophenone；2-(3-chlorophenoxy)-1-phenylethanone
• CAS: 19514-06-8
• 化学式: C₁₄H₁₁ClO₂
• mdl: MFCD15480505
• 分子量: 246.693
• InChiKey: QURJXQASERTKFX-UHFFFAOYSA-N

物化性质

• 沸点：
  392.9±22.0 °C(Predicted)
• 密度：
  1.225±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  α-(3-Chlorophenoxy)acetophenone 在 盐酸羟胺 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以91%的产率得到(NZ)-N-[2-(3-chlorophenoxy)-1-phenylethylidene]hydroxylamine
  参考文献：
  名称：

  Replacement of the Methylene of Dihydrochalcones with Oxygen: Synthesis and Biological Evaluation of 2-Phenoxyacetophenones

  摘要：

  With the aim of finding new bioactive compounds, a series of phenoxyacetophenone derivatives 2 were designed and synthesized as oxygen analogs of dihydrochalcones. Also, phenoxyacetophenones were converted to (Z)‐oxime derivatives 3 and their geometry were characterized by 1H‐NMR spectroscopy. The in vitro antifungal activity of compounds 2 and 3 was evaluated against Candida albicans, Candida glabrata, Saccharomyces cerevisiae, and Aspergillus niger using micro‐dilution method. In general, oxime derivative 3d containing 4‐fluorophenoxy moiety showed comparable or more potent antifungal activity (MICs = 15.63–31.25 μg/mL) with respect to the reference drug fluconazole against all tested yeasts. In addition, the antileishmanial activity of title compounds was determined against pormastigote form of Leishmania major. All compounds showed mild growth inhibitory activity against promastigotes. The most active compound was unsubstituted phenoxyacetophenone 2a (IC50 = 80 μg/mL). To anticipate the potential use as drugs, the target compounds were evaluated in their drug‐like properties. The in silico values of molecular descriptors for bioactive compounds 2a and 3d revealed that these compounds are within the range set by Lipinski’s ‘Rule of 5’ and show no violation of these rules. Moreover, bioactive compounds 2a and 3d are supposed to be non‐mutagenic and non‐tumorigenic, with no irritating or reproductive effects.

  DOI：

  10.1111/j.1747-0285.2012.01432.x
• 作为产物：
  描述：

  苯乙酮 在 potassium carbonate 、 copper(ll) bromide 作用下， 以 氯仿 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 α-(3-Chlorophenoxy)acetophenone
  参考文献：
  名称：

  新系列芳氧基苯乙酮缩氨基硫脲的合成和体外抗弓形虫活性。

  摘要：

  合成了一系列新的芳氧基苯乙酮缩氨基硫脲 4a-q 作为抗弓形虫剂。所有化合物均显示出对弓形虫感染细胞的显着抑制活性（IC50 值为 1.09-25.19 μg/mL）。4-氟苯氧基衍生物 (4l) 是最有效的化合物，对宿主细胞的选择性最高 (SI = 19)，优于标准药物乙胺嘧啶。SAR 研究表明，苯氧基苯乙酮的两个芳环上适当取代基的同时出现对效力和安全性很重要。对代表性化合物 4l 和 4p 的进一步体外实验表明，这些化合物在 5 μg/mL 的浓度下可以显着降低刚地弓形虫速殖子的活力，以及它们的感染率和细胞内增殖，与乙胺嘧啶相当。

  DOI：

  10.1007/s11030-019-09986-9
• 作为试剂：
  描述：

  2,5-二氯苯乙酮 、 苯酚 、 potassium carbonate 、 甲基叔丁基醚 在 铜 甲基叔丁基醚 、 sodium hydroxide 、 Sodium sulfate-III 、 甲醇 、 α-(3-Chlorophenoxy)acetophenone 作用下， 反应 10.5h， 以to obtain 236 g of 5-chloro-2-phenoxyacetophenone (compound XV) as an off-white solid的产率得到α-(3-Chlorophenoxy)acetophenone
  参考文献：
  名称：

  Processes for the preparation of 5-chloro-2-methyl-2,3,3A,12b-tetrahydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrole

  摘要：

  本发明提供了改进的工艺，用于制备5-氯-2-甲基-2,3,3a 12b-四氢-1H-二苯并[2,3:6,7]氧杂[4,5-c]吡咯，即阿塞那平。这些工艺允许在工业规模下以良好的产率和高立体选择性制备阿塞那平。

  公开号：

  US08580972B2

文献信息

• Electrochemistry of Electron-Transfer Probes. The Role of the Leaving Group in the Cleavage of Radical Anions of α-Aryloxyacetophenones¹
  作者：Mogens L. Andersen、N. Mathivanan、Danial D. M. Wayner

  DOI：10.1021/ja954093+

  日期：1996.1.1

  potential (E°) of α-phenoxyacetophenone has been determined from the voltammetric peak potential obtained by linear sweep voltammetry in combination with the rate constant for fragmentation of the radical anion which had been determined by laser flash photolysis. The E° values of a number of α-aryloxyacetophenones were then estimated from a correlation of the 13C chemical shifts of the carbonyl carbon

  α-苯氧基苯乙酮的形式还原电位 (E°) 由线性扫描伏安法获得的伏安峰电位结合激光闪光光解测定的自由基阴离子碎裂速率常数确定。然后根据羰基碳的 13C 化学位移的相关性和一系列取代的 α-苯胺基苯乙酮内的类似相关性（E° 与 13C 化学位移）估计许多 α-芳氧基苯乙酮的 E° 值。使用这些电位（在很宽的取代基范围内仅变化 34 mV），α-芳氧基苯乙酮自由基阴离子碎裂的速率常数由相应伏安波的数字模拟确定。显示碎裂速率常数与相应酚的 pKa 相关。然而，动力学范围太小，实验误差太大，无法区分线性和二次频率...
• PROCESSES FOR THE PREPARATION OF 5-CHLORO-2-METHYL-2,3,3A,12b-TETRAHYDRO-1H-DIBENZO[2,3:6,7]OXEPINO[4,5-c]PYRROLE
  申请人：BOSCH i LLADÓ Jordi

  公开号：US20120165545A1

  公开（公告）日：2012-06-28

  This invention provides improved processes for the preparation of 5-chloro-2-methyl-2,3,3a,12b-tetrahydro-1H-dibenzo[2,3:6,7]oxepino[4,5- c ]pyrrole, asenapine. These processes allow the preparation of asenapine at industrial scale in good yields and high stereoselectivity.

  本发明提供了改进的制备5-氯-2-甲基-2,3,3a,12b-四氢-1H-二苯并[2,3:6,7]氧杂[4,5-c]吡咯，即阿塞那平的工艺。这些工艺可以在工业规模下高产率和高立体选择性地制备阿塞那平。
• Processes for the preparation of 5-chloro-2-methyl-2,3,3a,12b-tetrahydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrole
  申请人：Medichem, S.A.

  公开号：EP2468751A2

  公开（公告）日：2012-06-27

  This invention provides improved processes for the preparation of 5-chloro-2-methyl-2,3,3a,12b-tetrahydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrole, asenapine. These processes allow the preparation of asenapine at industrial scale in good yields and high stereoselectivity.

  本发明提供了制备 5-氯-2-甲基-2,3,3a,12b-四氢-1H-二苯并[2,3:6,7]氧杂卓[4,5-c]吡咯，即阿塞那平的改进工艺。通过这些工艺，可以在工业规模上以良好的产率和较高的立体选择性制备阿塞那平。
• Effect of ring substitution on the photochemistry of .alpha.-(aryloxy)acetophenones
  作者：J. C. Netto-Ferreira、I. G. J. Avellar、J. C. Scaiano

  DOI：10.1021/jo00288a019

  日期：1990.1
• ROCHE, M.;CERUTTI, E., ANN. SCI. UNIV. BESANCON. CHEM., 1981, N 2, 16 P.
  作者：ROCHE, M.、CERUTTI, E.

  DOI：——

  日期：——