4-(氯甲基)苯基特戊酸酯 | 89115-54-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 中文名称: 4-(氯甲基)苯基特戊酸酯
• 英文名称: 4-(chloromethyl)phenyl pivalate
• 英文别名: Propanoic acid, 2,2-dimethyl-, 4-(chloromethyl)phenyl ester；[4-(chloromethyl)phenyl] 2,2-dimethylpropanoate
• CAS: 89115-54-8
• 化学式: C₁₂H₁₅ClO₂
• 分子量: 226.703
• InChiKey: ITUNDGWVHYGLJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2915900090

反应信息

• 作为反应物：
  描述：

  4-(氯甲基)苯基特戊酸酯 在 silver nitrate 作用下， 以 乙腈 为溶剂， 反应 1.5h， 生成 4-(nitrooxymethyl)phenyl pivalate
  参考文献：
  名称：

  Chemical Insights in the Concept of Hybrid Drugs:  The Antitumor Effect of Nitric Oxide-Donating Aspirin Involves A Quinone Methide but Not Nitric Oxide nor Aspirin

  摘要：

  Hybrid drug 1 (NO-ASA) continues to attract intense research from chemists and biologists alike. It consists of ASA and a -ONO2 group connected through a spacer and is in preclinical development as an antitumor drug. We report that, contrary to current beliefs, neither ASA nor NO contributes to this antitumor effect. Rather, an unsubstituted QM was identified as the sole cytotoxic agent. QM forms from 1 after carboxylic ester hydrolysis and, in accordance with the HSAB theory, selectively reacts with cellular GSH, which in turn triggers cell death. Remarkably, a derivative lacking ASA and the -ONO2 group is 10 times more effective than 1. Thus, our data provide a conclusive molecular mechanism for the antitumor activity of 1. Equally importantly, we show for the first time that a "presumed invisible" linker in a hybrid drug is not so invisible after all and is in fact solely responsible for the biological effect.

  DOI：

  10.1021/jm061371e
• 作为产物：
  描述：

  4-(羟基甲基)苯基特戊酸酯 在 吡啶 、 氯化亚砜 作用下， 以 乙醚 为溶剂， 反应 12.5h， 以94%的产率得到4-(氯甲基)苯基特戊酸酯
  参考文献：
  名称：

  镍催化未活化烯烃的不对称还原芳基苄基化反应

  摘要：

  在这里，我们报道了使用苄基氯作为挑战性偶合体的镍催化的芳基碘化物系链的未活化烯烃的镍催化不对称两组分还原二碳官能化。该芳基苄基化反应能够以高度对映选择性的方式高效合成具有季铵立体中心且对敏感性官能团具有高耐受性的多种苯稠合环状化合物。初步的机理研究表明了自由基链反应机理。

  DOI：

  10.1021/acs.orglett.0c00688

文献信息

• Synthesis of Multisubstituted Allylic Alcohols via a Nickel-Catalyzed Cross-Electrophile Ring-Opening Reaction
  作者：Weitao Hu、Zhiyang Lin、Chuan Wang

  DOI：10.1021/acs.orglett.2c02199

  日期：2022.8.12

  cross-electrophile ring-opening reaction of vinyl epoxides wherein aryl iodides, alkyl iodides, and benzyl chlorides can all serve as the electrophilic coupling partners, providing a new approach to preparing multisubstituted allylic alcohols. This new method features broad substrate scope (76 examples), good step-economy, and high L/B- and E/Z selectivity as well as mild reaction conditions.

  在此，我们报道了一种镍催化的乙烯基环氧化物的交叉亲电试剂开环反应，其中芳基碘化物、烷基碘化物和苄基氯都可以作为亲电偶联伙伴，为制备多取代烯丙醇提供了一种新方法。这种新方法具有广泛的底物范围（76 个实例）、良好的步骤经济性、高 L/B- 和E / Z选择性以及温和的反应条件。
• US4539383A
  申请人：——

  公开号：US4539383A

  公开（公告）日：1985-09-03
• Chemical Insights in the Concept of Hybrid Drugs:  The Antitumor Effect of Nitric Oxide-Donating Aspirin Involves A Quinone Methide but Not Nitric Oxide nor Aspirin
  作者：Niels Hulsman、Jan Paul Medema、Carina Bos、Aldo Jongejan、Rob Leurs、Martine J. Smit、Iwan J. P. de Esch、Dick Richel、Maikel Wijtmans

  DOI：10.1021/jm061371e

  日期：2007.5.1

  Hybrid drug 1 (NO-ASA) continues to attract intense research from chemists and biologists alike. It consists of ASA and a -ONO2 group connected through a spacer and is in preclinical development as an antitumor drug. We report that, contrary to current beliefs, neither ASA nor NO contributes to this antitumor effect. Rather, an unsubstituted QM was identified as the sole cytotoxic agent. QM forms from 1 after carboxylic ester hydrolysis and, in accordance with the HSAB theory, selectively reacts with cellular GSH, which in turn triggers cell death. Remarkably, a derivative lacking ASA and the -ONO2 group is 10 times more effective than 1. Thus, our data provide a conclusive molecular mechanism for the antitumor activity of 1. Equally importantly, we show for the first time that a "presumed invisible" linker in a hybrid drug is not so invisible after all and is in fact solely responsible for the biological effect.
• Nickel-Catalyzed Asymmetric Reductive Arylbenzylation of Unactivated Alkenes
  作者：Youxiang Jin、Haobo Yang、Chuan Wang

  DOI：10.1021/acs.orglett.0c00688

  日期：2020.4.3

  Herein, we report a nickel-catalyzed asymmetric two-component reductive dicarbofunctionalization of aryl iodide-tethered unactivated alkenes using benzyl chlorides as the challenging coupling partner. This arylbenzylation reaction enables the efficient synthesis of diverse benzene-fused cyclic compounds bearing a quaternary stereocenter with a high tolerance of sensitive functionalities in highly enantioselective

  在这里，我们报道了使用苄基氯作为挑战性偶合体的镍催化的芳基碘化物系链的未活化烯烃的镍催化不对称两组分还原二碳官能化。该芳基苄基化反应能够以高度对映选择性的方式高效合成具有季铵立体中心且对敏感性官能团具有高耐受性的多种苯稠合环状化合物。初步的机理研究表明了自由基链反应机理。