(4-chloro-phenyl)-(3,5-dimethoxy-phenyl)-methanone | 951892-01-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4-chloro-phenyl)-(3,5-dimethoxy-phenyl)-methanone
• 英文别名: (4-chlorophenyl)(3,5-dimethoxyphenyl)methanone；4-Chloro-3',5'-dimethoxybenzophenone；(4-chlorophenyl)-(3,5-dimethoxyphenyl)methanone
• CAS: 951892-01-6
• 化学式: C₁₅H₁₃ClO₃
• mdl: MFCD09801533
• 分子量: 276.719
• InChiKey: ZMKICALUILMFCB-UHFFFAOYSA-N

物化性质

• 沸点：
  424.6±45.0 °C(Predicted)
• 密度：
  1.216±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.133
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4-chloro-phenyl)-(3,5-dimethoxy-phenyl)-methanone 、 Dimethylzinc 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以88.6%的产率得到1-[1-(4-氯-苯基)-1-甲基-乙基]-3,5-二甲氧基-苯
  参考文献：
  名称：

  Exploring the substituent effects on a novel series of C1′-dimethyl-aryl Δ8-tetrahydrocannabinol analogs

  摘要：

  The synthesis and characterization of novel C1'-phenyl-substituted Delta(8)-THC analogs were previously reported by our laboratory. Within this small series of compounds, the C1'-dimethyl phenyl group was found to impart 13.5-fold selectivity for the CB2 receptor with a K-i 0.91 nM. The current study expands on the previous report by evaluating the effects of aromatic ring substitution on CB1 and CB2 receptor subtype binding and selectivity. The ring substituents synthesized in this study include aliphatic, halogen, nitrile, and acetamido functional groups. In addition, the isosteric replacement of the phenyl group by thiophene was evaluated. The anti-glioma activities of selected compounds were evaluated in vitro and compared to the lead compound 2. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.05.034
• 作为产物：
  描述：

  4-氯苯甲酰氯 在 吡啶 、 lithium chloro-isopropyl-magnesium chloride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.25h， 生成 (4-chloro-phenyl)-(3,5-dimethoxy-phenyl)-methanone
  参考文献：
  名称：

  连续流动中带有酯基的芳基和杂芳基镁试剂的选择性酰化。

  摘要：

  易于获得的有机镁试剂与市售酯的选择性酰化反应可在方便的温度下以较短的停留时间连续进行。流动条件使我们能够防止半缩醛中间体过早坍塌，尽管非低温条件也是如此，因此可以提供高收率的酮。整个过程中，酯和/或格利雅（Grignard）的配位能力对于反应结果至关重要。通过使用2-羟基酯衍生物作为底物获得几种双芳基酮来利用这一点。

  DOI：

  10.1021/acs.orglett.9b04254

文献信息

• Selective Acylation of Aryl- and Heteroarylmagnesium Reagents with Esters in Continuous Flow
  作者：Benjamin Heinz、Dimitrije Djukanovic、Maximilian A. Ganiek、Benjamin Martin、Berthold Schenkel、Paul Knochel

  DOI：10.1021/acs.orglett.9b04254

  日期：2020.1.17

  A selective acylation of readily accessible organomagnesium reagents with commercially available esters proceeds at convenient temperatures and short residence times in continuous flow. Flow conditions allow us to prevent premature collapse of the hemiacetal intermediates despite noncryogenic conditions, thus furnishing ketones in good yields. Throughout, the coordinating ability of the ester and/or

  易于获得的有机镁试剂与市售酯的选择性酰化反应可在方便的温度下以较短的停留时间连续进行。流动条件使我们能够防止半缩醛中间体过早坍塌，尽管非低温条件也是如此，因此可以提供高收率的酮。整个过程中，酯和/或格利雅（Grignard）的配位能力对于反应结果至关重要。通过使用2-羟基酯衍生物作为底物获得几种双芳基酮来利用这一点。
• Exploring the substituent effects on a novel series of C1′-dimethyl-aryl Δ8-tetrahydrocannabinol analogs
  作者：Mathangi Krishnamurthy、Steven Gurley、Bob M. Moore II

  DOI：10.1016/j.bmc.2008.05.034

  日期：2008.7.1

  The synthesis and characterization of novel C1'-phenyl-substituted Delta(8)-THC analogs were previously reported by our laboratory. Within this small series of compounds, the C1'-dimethyl phenyl group was found to impart 13.5-fold selectivity for the CB2 receptor with a K-i 0.91 nM. The current study expands on the previous report by evaluating the effects of aromatic ring substitution on CB1 and CB2 receptor subtype binding and selectivity. The ring substituents synthesized in this study include aliphatic, halogen, nitrile, and acetamido functional groups. In addition, the isosteric replacement of the phenyl group by thiophene was evaluated. The anti-glioma activities of selected compounds were evaluated in vitro and compared to the lead compound 2. (c) 2008 Elsevier Ltd. All rights reserved.