5-(2-chlorobenzyl)-2-furoic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 5-(2-chlorobenzyl)-2-furoic acid
• 英文别名: 5-[(2-chlorophenyl)methyl]furan-2-carboxylic acid
• 化学式: C₁₂H₉ClO₃
• 分子量: 236.655
• InChiKey: YRUPEIZURHOLHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  50.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(2-chlorobenzyl)-2-furoic acid 在 氯化亚砜 、 三(2-甲氧基苯基)膦 、 caesium carbonate 、 palladium dichloride 、 三甲基乙酸 作用下， 以 甲苯 为溶剂， 反应 3.5h， 生成 2-(2-chlorobenzyl)-5-ethylfuro[2,3-c]quinolin-4(5H)-one
  参考文献：
  名称：

  Regioselective and Stereoselective Pd-Catalyzed Intramolecular Arylation of Furans: Access to Spirooxindoles and 5H-Furo[2,3-c]quinolin-4-ones

  摘要：

  Herein, we report regio- and stereoselective intramolecular direct arylations of N-(2-bromophenyl)-2-furancarboxamides 1 to produce spirooxindoles 2 and 5H-furo[2,3-c]quinolin-4-ones 3 under different reaction conditions. Specifically, in the presence of Pd(PPh3)(4) as a catalyst, PPh3 as a ligand, and K2CO3 as a base, substrates 1 underwent intramolecular alpha-arylation, possibly via a Heck insertion pathway, to provide 2, with the Zeta-isomer being favored. When the base was t-BuOLi and R-1 was an aryl group, the reaction favored Epsilon-2, possibly via an electrophilic palladation pathway. In contrast, in the presence of PdCl2 as a catalyst, (o-OMePh)(3)P as a ligand, and PivOH as an additive, substrates 1 underwent intramolecular beta-arylation to provide 3, possibly via a concerted metalation-deprotonation process.

  DOI：

  10.1021/acs.joc.6b01774
• 作为产物：
  描述：

  2-糠酸甲酯 在 sodium hydroxide 、 三氯化铁 作用下， 生成 5-(2-chlorobenzyl)-2-furoic acid
  参考文献：
  名称：

  金属型选择性抑制：大肠杆菌蛋氨酸氨基肽酶的Mn（II）形式选择性抑制剂的合成和结构活性分析。

  摘要：

  蛋氨酸氨基肽酶（MetAP）是开发新型抗菌，抗真菌和抗癌药物的有希望的目标。然而，其生理相关的金属离子仍有待确定，并且其抑制剂需要抑制体内金属形态。基于通过高通量筛选发现的Mn（II）形式选择性抑制剂作为前导物，制备了一系列5-苯基呋喃-2-羧酸类似物，然后在Co（II）-，Mn（II）-上进行了评估。 MetAP的Ni，II（II）和Fe（II）形式，以定义对其抑制能力和金属形态选择性负责的结构元素。苯环上的各种取代改变了它们对Mn（II）形式的效力，但没有改变其对金属形式的选择性。我们得出结论，羧基对Mn（II）离子的优先配位是其对Mn（II）形式的超强选择性的主要决定因素。将羧酸盐更改为异羟肟酸酯会改变其结合和区分不同金属离子的能力，并且异羟肟酸酯衍生物在测试的金属型中变为非选择性。

  DOI：

  10.1016/j.bmcl.2005.09.019

文献信息

• MNDZHOYAN, SH. L.;KRAMER, M. S.;ALEKSANYAN, M. V.;TER-ZAXARYAN, YU. Z.;KA+, XIM. -FARMATS. ZH., 22,(1988) N 9, S. 1091-1094
  作者：MNDZHOYAN, SH. L.、KRAMER, M. S.、ALEKSANYAN, M. V.、TER-ZAXARYAN, YU. Z.、KA+

  DOI：——

  日期：——
• REGULATED BIOCIRCUIT SYSTEMS
  申请人：Obsidian Therapeutics, Inc.

  公开号：US20190192691A1

  公开（公告）日：2019-06-27

  The present invention provides regulatable biocircuit systems. Such systems provide modular and tunable protein expression systems in support of the discovery and development of therapeutic modalities.
• IDENTIFICATION AND TARGETED MODULATION OF GENE SIGNALING NETWORKS
  申请人：CAMP4 THERAPEUTICS CORPORATION

  公开号：US20210254056A1

  公开（公告）日：2021-08-19

  The present invention provides methods and compositions for the evaluation, alteration and/or optimization of gene signaling. Methods and systems are also provided which exploit the information generated in the identification of new targets and non-canonical signaling pathways.
• Metalloform-selective inhibition: Synthesis and structure–activity analysis of Mn(II)-form-selective inhibitors of Escherichia coli methionine aminopeptidase
  作者：Qing-Qing Huang、Min Huang、Fa-Jun Nan、Qi-Zhuang Ye

  DOI：10.1016/j.bmcl.2005.09.019

  日期：2005.12

  relevant metal ion remains to be defined, and its inhibitors need to inhibit the in vivo metalloform. Based on the Mn(II)-form-selective inhibitors discovered by high throughput screening as leads, a series of analogs of 5-phenylfuran-2-carboxylic acid was prepared and subsequently evaluated on Co(II)-, Mn(II)-, Ni(II)-, and Fe(II)-forms of Escherichia coli MetAP, in order to define the structural elements

  蛋氨酸氨基肽酶（MetAP）是开发新型抗菌，抗真菌和抗癌药物的有希望的目标。然而，其生理相关的金属离子仍有待确定，并且其抑制剂需要抑制体内金属形态。基于通过高通量筛选发现的Mn（II）形式选择性抑制剂作为前导物，制备了一系列5-苯基呋喃-2-羧酸类似物，然后在Co（II）-，Mn（II）-上进行了评估。 MetAP的Ni，II（II）和Fe（II）形式，以定义对其抑制能力和金属形态选择性负责的结构元素。苯环上的各种取代改变了它们对Mn（II）形式的效力，但没有改变其对金属形式的选择性。我们得出结论，羧基对Mn（II）离子的优先配位是其对Mn（II）形式的超强选择性的主要决定因素。将羧酸盐更改为异羟肟酸酯会改变其结合和区分不同金属离子的能力，并且异羟肟酸酯衍生物在测试的金属型中变为非选择性。
• Regioselective and Stereoselective Pd-Catalyzed Intramolecular Arylation of Furans: Access to Spirooxindoles and 5<i>H</i>-Furo[2,3-<i>c</i>]quinolin-4-ones
  作者：Jianchao Liu、Hui Peng、Yongjie Yang、Huanfeng Jiang、Biaolin Yin

  DOI：10.1021/acs.joc.6b01774

  日期：2016.10.21

  Herein, we report regio- and stereoselective intramolecular direct arylations of N-(2-bromophenyl)-2-furancarboxamides 1 to produce spirooxindoles 2 and 5H-furo[2,3-c]quinolin-4-ones 3 under different reaction conditions. Specifically, in the presence of Pd(PPh3)(4) as a catalyst, PPh3 as a ligand, and K2CO3 as a base, substrates 1 underwent intramolecular alpha-arylation, possibly via a Heck insertion pathway, to provide 2, with the Zeta-isomer being favored. When the base was t-BuOLi and R-1 was an aryl group, the reaction favored Epsilon-2, possibly via an electrophilic palladation pathway. In contrast, in the presence of PdCl2 as a catalyst, (o-OMePh)(3)P as a ligand, and PivOH as an additive, substrates 1 underwent intramolecular beta-arylation to provide 3, possibly via a concerted metalation-deprotonation process.