methyl 4-(chloro(hydroxyimino)methyl)benzoate | 101023-70-5

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 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: methyl 4-(chloro(hydroxyimino)methyl)benzoate
• 英文别名: Methyl 4-[chloro(hydroxyimino)methyl]benzoate；methyl 4-(C-chloro-N-hydroxycarbonimidoyl)benzoate
• CAS: 101023-70-5
• 化学式: C₉H₈ClNO₃
• 分子量: 213.62
• InChiKey: OSEDFBIVKALVNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  58.9
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2928000090

反应信息

• 作为反应物：
  描述：

  methyl 4-(chloro(hydroxyimino)methyl)benzoate 在 sodium hydroxide 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 生成 1H-苯并[d][1,2,3]噻唑-1-基 4-(5-(4-(戊基氧基)苯基)异噁唑-3-基)苯甲酸
  参考文献：
  名称：

  FK463, a Novel Water-soluble Echinocandin Lipopeptide. Synthesis and Antifungal Activity.

  摘要：

  DOI：

  10.7164/antibiotics.52.674
• 作为产物：
  描述：

  methyl 4-((tert-butoxyimino)chloromethyl)benzoate 在 三氟乙酸 作用下， 以90%的产率得到methyl 4-(chloro(hydroxyimino)methyl)benzoate
  参考文献：
  名称：

  Synthesis and antifungal evaluation of pentyloxyl-diphenylisoxazoloyl pneumocandins and echinocandins

  摘要：

  Echinocandins and pneumocandins are classes of lipocyclohexapeptides that are broad spectrum antifungal agents. They inhibit fungal specific 1,3-beta-glucan synthase activity which is an essential component of the fungal cell wall. Chemical modifications of these two leads have produced three clinical agents namely caspofungin, micafungin and anidulafungin. The presence of hydroxy-glutamine versus threonine and unsaturated linear fatty acid versus branched chain saturated fatty acid differentiate the two classes of compounds with profound differences in their hemolytic properties. In the current study, we have replaced the side chain of the cyclohexapeptides with a common aromatic heterocyclic acyl side chain and compared the biological activities of the cores head-to-head and for the first time demonstrated the role played by the acyl chain and the hydroxy-glutamine for the antifungal potency. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.115

文献信息

• [EN] SUBSTITUTED PYRIMIDINES<br/>[FR] PYRIMIDINES SUBSTITUÉES
  申请人：MERCK SHARP & DOHME

  公开号：WO2013040790A1

  公开（公告）日：2013-03-28

  Disclosed are substituted pyrimidines useful as HIF prolyl hydroxylase inhibitors to treat anemia and like conditions.

  公开了作为HIF脯氨酰羟化酶抑制剂的有用取代嘧啶，用于治疗贫血及类似病症。
• Facile One-Pot Transformation of Primary Alcohols into 3-Aryl- and 3-Alkyl-isoxazoles and -pyrazoles
  作者：Eiji Kobayashi、Hideo Togo

  DOI：10.1055/s-0039-1690102

  日期：2019.10

  Abstract Various primary alcohols were smoothly transformed into 3-aryl- and 3-alkylisoxazoles in good yields in one pot by successive treatment with PhI(OAc)2 in the presence of TEMPO, NH2OH, and then NCS, followed by reaction with alkynes in the presence of Et3N. Similarly, various primary alcohols were smoothly transformed into 3-aryl- and 3-alkylpyrazoles in good yields in one pot by successive

  抽象的 通过在TEMPO，NH 2 OH和NCS的存在下依次用PhI（OAc）2连续处理，然后与炔烃反应，在一个锅中将各种伯醇顺利地转化成高产率的3-芳基-和3-烷基异恶唑。的Et存在下3 N.类似地，多种伯醇被顺利转化为3-芳基-和3- alkylpyrazoles以良好的收率以一锅煮的通过用岛（OAC）连续处理2在TEMPO，PhNHNH存在2，然后NCS和癸基甲基硫醚，然后在Et 3存在下与炔烃反应因此，3-芳基-和3-烷基异唑和3-芳基和3-烷基吡唑都可以在无过渡金属的条件下由易得的伯醇在一个罐中制备。 通过在TEMPO，NH 2 OH和NCS的存在下依次用PhI（OAc）2连续处理，然后与炔烃反应，在一个锅中将各种伯醇顺利地转化成高产率的3-芳基-和3-烷基异恶唑。的Et存在下3 N.类似地，多种伯醇被顺利转化为3-芳基-和3- alkylpyrazoles以良好的收率以一锅煮的
• Discovery of novel 5-oxa-2,6-diazaspiro[3.4]oct-6-ene derivatives as potent, selective, and orally available somatostatin receptor subtype 5 (SSTR5) antagonists for treatment of type 2 diabetes mellitus
  作者：Hideki Hirose、Takeshi Yamasaki、Masaki Ogino、Ryo Mizojiri、Yumiko Tamura-Okano、Hiroaki Yashiro、Yo Muraki、Yoshihide Nakano、Jun Sugama、Akito Hata、Shinji Iwasaki、Masanori Watanabe、Tsuyoshi Maekawa、Shizuo Kasai

  DOI：10.1016/j.bmc.2017.06.007

  日期：2017.8

  enhancement in potency, however, the 4-benzoic acid derivative 10c exhibited moderate human ether-a-go-go related gene (hERG) inhibitory activity. A subsequent optimization study revealed that replacement of the 4-benzoic acid with an isonipecotic acid dramatically reduced hERG inhibition (5.6% inhibition at 30 μM) by eliminating π-related interaction with hERG K+ channel, which resulted in the identification

  生长抑素受体亚型5（SSTR5）已成为2型糖尿病的新型有吸引力的药物靶标。从作为内部命中化合物的N-苄基氮杂环丁烷衍生物1和2开始，我们探索了将羧基引入1的末端苯中以通过异恶唑啉3位上的取代基的组合增强SSTR5拮抗活性的方法。 。在苯环的4位上引入羧基会显着提高效力，但是4-苯甲酸衍生物10c表现出中等程度的人类以太相关基因（hERG）抑制活性。随后的优化研究表明，通过消除与hERG K +通道的π相关相互作用，用异二十二烷酸替换4-苯甲酸显着降低了hERG抑制（在30μM时抑制5.6％），从而鉴定出1-（ 2-（（（2,6-二乙氧基-4'-氟联苯-4-基）甲基）-5-氧杂-2,6-二氮杂螺[3.4] oct-6-en-7-yl）哌啶-4-羧酸25a（hSSTR5 / mSSTR5 IC 50  = 9.6 / 57 nM）。在高脂饮食喂养的C57BL / 6J小鼠中口服25a可以以葡萄
• Stereospecific 1,4‐Metallate Shift Enables Stereoconvergent Synthesis of Ketoximes
  作者：Kai Yang、Feng Zhang、Tongchang Fang、Guan Zhang、Qiuling Song

  DOI：10.1002/anie.201906057

  日期：2019.9.16

  Reported herein is a stereospecific 1,4-metallate rearrangement for single-geometry ketoxime synthesis from oxime chlorides and arylboronic acids. This strategy exhibits broad substrate scope with excellent stereoselectivity under mild reaction conditions. In comparison with the conventional approaches, each configuration of unsymmetric diaryl oximes, as well as the thermodynamically less stable Z isomer

  本文报道了用于由肟氯化物和芳基硼​​酸合成单几何型酮肟的立体有规的1,4-金属盐重排。该策略在温和的反应条件下具有宽泛的底物范围和出色的立体选择性。与常规方法相比，可以选择性地并且排他地获得不对称二芳基肟的每种构型以及芳基烷基酮肟的热力学上较不稳定的Z异构体。一类未开发的分子，不对称二芳基肟和芳基烷基肟的Z异构体的反应性使得能够有效地获得具有单一构型的相应异喹啉，异喹啉N-氧化物和酰胺。
• Formation of Amidinyl Radicals via Visible-Light-Promoted Reduction of <i>N</i>-Phenyl Amidoxime Esters and Application to the Synthesis of 2-Substituted Benzimidazoles
  作者：Gang Li、Ru He、Qiang Liu、Ziwen Wang、Yuxiu Liu、Qingmin Wang

  DOI：10.1021/acs.joc.9b01158

  日期：2019.7.5

  We have developed a new method for the synthesis of 2-substituted benzimidazoles via amidinyl radicals generated by visible-light-promoted reduction of N-phenyl amidoxime esters in the presence of an iridium photocatalyst. This is the first report of the use of N-phenyl amidoxime esters as amidinyl radical precursors, and the first use of substituted benzene rings as amidinyl radical acceptors. This

  我们已经开发了一种新的方法，该方法通过在铱光催化剂的存在下，由可见光促进的N-苯基a肟肟酯的还原反应生成的via基自由基合成2-取代的苯并咪唑。这是使用N-苯基a肟肟酯作为a基自由基前体的首次报道，也是取代苯环作为a基自由基受体的首次报道。该方法拓宽了底物的应用范围，克服了传统的2-取代苯并咪唑合成方法的缺点，该方法要求苛刻的反应条件，涉及难以制备的取代邻苯二胺底物，并产生酸性废物。