methyl 2-((4-fluorophenyl)thio)acetate | 226396-70-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: methyl 2-((4-fluorophenyl)thio)acetate
• 英文别名: (4-Fluoro-phenylsulfanyl)-acetic acid methyl ester；methyl 2-(4-fluorophenyl)sulfanylacetate
• CAS: 226396-70-9
• 化学式: C₉H₉FO₂S
• mdl: MFCD11174002
• 分子量: 200.234
• InChiKey: LBMJUVGSIFZRNR-UHFFFAOYSA-N

物化性质

• 沸点：
  261.2±25.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-((4-fluorophenyl)thio)acetate 在 N-甲基吗啉 、 4-二甲氨基吡啶 、 oxone 、 potassium trimethylsilonate 、 四丁基溴化铵 、 potassium carbonate 、 1-羟基苯并三唑 、 caesium carbonate 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.0h， 生成 4-[4-(4-chlorophenoxy)phenyl]sulfonyl-N-(oxan-2-yloxy)oxane-4-carboxamide
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of β- and α-Piperidine Sulfone Hydroxamic Acid Matrix Metalloproteinase Inhibitors with Oral Antitumor Efficacy

  摘要：

  alpha-Piperidine-beta-sulfone hydroxamate derivatives were explored that are potent for matrix metalloproteinases (MMP)-2, -9, and -13 and are sparing of MMP-1. The investigation of the beta-sulfones subsequently led to the discovery of hitherto unknown alpha-sulfone hydroxamates that are superior to the corresponding beta-sulfones in potency for target MMPs, selectivity vs MMP-1, and exposure when dosed orally. alpha-Tiperidine-alpha-sulfone, hydroxamate 35f (SC-276) was advanced through antitumor and antiangiogenesis assays and was selected for development. Compound 35f demonstrates excellent antitumor activity vs MX-1 breast tumor in mice when dosed orally as monotherapy or in combination with paclitaxel.

  DOI：

  10.1021/jm0500875
• 作为产物：
  描述：

  在 正丁基锂 、 8-甲基喹啉1-氧化物 、 氯[2-(二叔丁基磷)二苯基]金 、 双三氟甲烷磺酰亚胺银盐 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 10.0h， 生成 methyl 2-((4-fluorophenyl)thio)acetate
  参考文献：
  名称：

  金催化的硫炔炔氧化反应通过非碳烯路线形成苯硫基乙炔衍生物

  摘要：

  金催化的8-甲基喹啉氧化物氧化硫代炔烃可生成2-苯基硫代烯酮，可被醇有效地捕集。末端和内部的硫代炔烃在广泛的范围内带有酯，酮，烷基和肟取代基，从而显示出合成的效用。我们的密度泛函理论计算表明，用8-甲基喹啉氧化物对末端和内部硫代炔烃进行金催化的氧化反应可生成与金键合的乙烯酮中间体，而无需使用α-氧代金卡宾。

  DOI：

  10.1021/acs.orglett.9b01768

文献信息

• Aromatic sulfone hydroxamates and their use as protease inhibitors
  申请人：——

  公开号：US20040010019A1

  公开（公告）日：2004-01-15

  This invention is directed to aromatic sulfone hydroxamates (also known as “aromatic sulfone hydroxamic acids”) and salts thereof that, inter alia, inhibit matrix metalloproteinase (also known as “matrix metalloprotease” or “MMP”) activity and/or aggrecanase activity. This invention also is directed to a prevention or treatment method that comprises administering such a compound or salt in an MMP-inhibiting and/or aggrecanase-inhibiting effective amount to an animal, particularly a mammal having (or disposed to having) a pathological condition associated with MMP and/or aggrecanase activity.

  这项发明涉及芳香砜羟肟酸酯（也称为“芳香砜羟肟酸”）及其盐，该化合物在抑制基质金属蛋白酶（也称为“基质金属蛋白酶”或“MMP”）活性和/或聚集素酶活性方面具有作用。该发明还涉及一种预防或治疗方法，包括向动物，特别是患有（或易患）与MMP和/或聚集素酶活性相关的病理状况的哺乳动物，施用此类化合物或盐以达到抑制MMP和/或聚集素酶的有效量。
• HETEROCYCLIC DERIVED METALLOPROTEASE INHIBITORS
  申请人：Zhang Yue-Mei

  公开号：US20080103129A1

  公开（公告）日：2008-05-01

  This invention provides novel heterocyclic derived matrix metalloprotease inhibitors of the formula: and pharmaceutical compositions comprising same, useful for treating disorders ameliorated by antagonizing matrix metalloproteases. This invention also provides therapeutic and prophylactic methods using the instant pharmaceutical compositions.

  这项发明提供了一种新颖的杂环衍生物基质金属蛋白酶抑制剂的化学式，以及包含同样化合物的药物组合物，用于治疗通过拮抗基质金属蛋白酶而改善的疾病。该发明还提供了使用即时药物组合物的治疗和预防方法。
• Microwave-assisted synthesis of β-amino-α,β-unsaturated esters: a rapid and efficient access to (Z)-methyl 3-amino-2-substituted acrylate
  作者：Han Cao、Xue-jing Liu、Peng-fei Li、Fu-sheng Bie、Yi-jun Shi、Peng Yan、Ying Han

  DOI：10.1080/00397911.2021.1923751

  日期：2021.7.18

  Abstract We report a two-step rapid and efficient synthesis of β-amino-α,β-unsaturated esters. Microwave-assisted synthesis was used throughout the process. Seventeen β-amino-α,β-unsaturated esters were produced in excellent yields and short reaction times. The effects of the heating method and substituents, especially the o-substituted group of the phenols or thiophenols, were investigated. A plausible

  摘要 我们报告了 β-氨基-α,β-不饱和酯的两步快速有效合成。在整个过程中使用微波辅助合成。以极好的收率和较短的反应时间生产了 17 种 β-氨基-α,β-不饱和酯。研究了加热方法和取代基的影响，特别是苯酚或苯硫酚的邻取代基团。还提出了一个合理的反应机制。
• 6-Substituted pyrido-pyrimidines
  申请人：——

  公开号：US20040116698A1

  公开（公告）日：2004-06-17

  The present invention provides compounds of the Formula I and II: 1 wherein R 1 , R 3 , W, Z, X 1 , X 2 , Ar 1 , R 8 and R 9 are as defined herein, and methods and intermediates for their preparation and uses thereof.

  本发明提供公式I和II的化合物：1其中R1、R3、W、Z、X1、X2、Ar1、R8和R9如本文所定义，以及其制备方法和中间体以及它们的用途。
• Reverse hydroxamate inhibitors of matrix metalloproteinases
  申请人：Abbott Laboratories

  公开号：US06294573B1

  公开（公告）日：2001-09-25

  Compounds having the formula are matrix metalloproteinase inhibitors. Also disclosed are matrix metalloproteinase-inhibiting compositions and methods of inhibiting matrix metalloproteinase in a mammal.

  具有公式的化合物是基质金属蛋白酶抑制剂。本文还公开了基质金属蛋白酶抑制剂组合物和在哺乳动物中抑制基质金属蛋白酶的方法。