4-[1,3]dioxolan-2-ylbenzoyl chloride | 951655-56-4

• 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-[1,3]dioxolan-2-ylbenzoyl chloride
• 英文别名: 4-(1,3-Dioxolan-2-yl)benzoyl chloride
• CAS: 951655-56-4
• 化学式: C₁₀H₉ClO₃
• 分子量: 212.633
• InChiKey: KVMPVIPQAKIOTI-UHFFFAOYSA-N

物化性质

• 熔点：
  67.0-67.1 °C
• 沸点：
  320.9±37.0 °C(Predicted)
• 密度：
  1.317±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 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-[1,3]dioxolan-2-ylbenzoyl chloride 在 sodium hydroxide 、 正丁基锂 、 高氯酸 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 trans-3-[4-(1-benzenesulfonyl-1H-indole-2-carbonyl)phenyl]-N-(tetrahydropyran-2-yloxy)acrylamide
  参考文献：
  名称：

  2-Aroylindoles and 2-Aroylbenzofurans with N-Hydroxyacrylamide Substructures as a Novel Series of Rationally Designed Histone Deacetylase Inhibitors

  摘要：

  Histone deacetylase (HDAC) inhibitors are considered to be drugs for targeted cancer therapy and second-generation HDIs are currently being tested in clinical trials. Here, we report on the synthesis and biological evaluation of a novel HDAC inhibitor scaffold with the hydroxamate Zn2+ complexing headgroup, selected from the 2-aroylindol motif. Inhibition of nuclear extract HDAC and recombinant HDAC I as well as induction of histone H3K(9+14) hyperacetylation mediated by E-N-hydroxy-(2-aroylindole)acrylamides or E-Nhydroxy-(2-aroylbenzofuran)acrylamides were studied. Moreover, the cytotoxic activity, the effects on the cell cycle, and historic H3S(10) phosphorylation of selected compounds were determined. By use of a panel of 24 different human tumor cell lines, mean IC50 values of the most potent analogues 6c and 7b were 0.75 and 0.65 mu M, respectively. The novel compounds were shown to be no substrates of the P-glycoprotein drug transporter. Comparable to N-1-hydroxy-N-8-phenyloctanediamide "2 (SAHA)", cells in the S phase of the cell cycle are depleted, with partial arrest in G1 and G2/M and finally induction of massive apoptosis.

  DOI：

  10.1021/jm0703136
• 作为产物：
  描述：

  4-(1,3-dioxolan-2-yl)benzoic acid 在 草酰氯 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-[1,3]dioxolan-2-ylbenzoyl chloride
  参考文献：
  名称：

  涉及邻位 C-H 键活化的镍催化螯合辅助转化：芳族酰胺与炔烃的区域选择性氧化环加成

  摘要：

  尽管使用镍络合物（Kleiman, JP; Dubeck, MJ Am. Chem. Soc. 1963, 85, 1544）实现了涉及裂解CH键的邻位金属化的开创性例子，但尚未报道使用镍络合物进行催化的例子。在这项工作中，利用螯合辅助，如芳族酰胺与炔烃的氧化环加成，实现了 Ni 催化的邻位 CH 键的转化。

  DOI：

  10.1021/ja206850s

文献信息

• Nickel-Catalyzed Chelation-Assisted Transformations Involving Ortho C–H Bond Activation: Regioselective Oxidative Cycloaddition of Aromatic Amides to Alkynes
  作者：Hirotaka Shiota、Yusuke Ano、Yoshinori Aihara、Yoshiya Fukumoto、Naoto Chatani

  DOI：10.1021/ja206850s

  日期：2011.9.28

  examples of catalysis using nickel complexes have been reported. In this work, the Ni-catalyzed transformation of ortho C-H bonds utilizing chelation assistance, such as oxidative cycloaddition of aromatic amides with alkynes, has been achieved.

  尽管使用镍络合物（Kleiman, JP; Dubeck, MJ Am. Chem. Soc. 1963, 85, 1544）实现了涉及裂解CH键的邻位金属化的开创性例子，但尚未报道使用镍络合物进行催化的例子。在这项工作中，利用螯合辅助，如芳族酰胺与炔烃的氧化环加成，实现了 Ni 催化的邻位 CH 键的转化。
• 2-Aroylindoles and 2-Aroylbenzofurans with <i>N-</i>Hydroxyacrylamide Substructures as a Novel Series of Rationally Designed Histone Deacetylase Inhibitors
  作者：Siavosh Mahboobi、Andreas Sellmer、Heymo Höcher、Christian Garhammer、Herwig Pongratz、Thomas Maier、Thomas Ciossek、Thomas Beckers

  DOI：10.1021/jm0703136

  日期：2007.9.1

  Histone deacetylase (HDAC) inhibitors are considered to be drugs for targeted cancer therapy and second-generation HDIs are currently being tested in clinical trials. Here, we report on the synthesis and biological evaluation of a novel HDAC inhibitor scaffold with the hydroxamate Zn2+ complexing headgroup, selected from the 2-aroylindol motif. Inhibition of nuclear extract HDAC and recombinant HDAC I as well as induction of histone H3K(9+14) hyperacetylation mediated by E-N-hydroxy-(2-aroylindole)acrylamides or E-Nhydroxy-(2-aroylbenzofuran)acrylamides were studied. Moreover, the cytotoxic activity, the effects on the cell cycle, and historic H3S(10) phosphorylation of selected compounds were determined. By use of a panel of 24 different human tumor cell lines, mean IC50 values of the most potent analogues 6c and 7b were 0.75 and 0.65 mu M, respectively. The novel compounds were shown to be no substrates of the P-glycoprotein drug transporter. Comparable to N-1-hydroxy-N-8-phenyloctanediamide "2 (SAHA)", cells in the S phase of the cell cycle are depleted, with partial arrest in G1 and G2/M and finally induction of massive apoptosis.