methyl 2-(2-fluoro-4-hydroxyphenoxy)propionate | 99045-15-5

• 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 2-(2-fluoro-4-hydroxyphenoxy)propionate
• 英文别名: methyl 2-(2-fluoro-4-hydroxyphenoxy)propanoate
• CAS: 99045-15-5
• 化学式: C₁₀H₁₁FO₄
• 分子量: 214.193
• InChiKey: DSHKBLUNGHNNLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-(2-fluoro-4-hydroxyphenoxy)propionate 在 sodium hydroxide 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 4.0h， 生成 2-[4-(7-Chloro-quinoxalin-2-yloxy)-2-fluoro-phenoxy]-propionic acid
  参考文献：
  名称：

  Synthetic modification of the 2-oxypropionic acid moiety in 2-{4-[(7-chloro-2-quinoxalinyl)oxy]phenoxy}propionic acid (XK469), and consequent antitumor effects. Part 4

  摘要：

  The criteria for the activity of 2-{4-[(7-chloro-2 -quinoxalinyl)oxy]phenoxy}propionic acid (XK469) and 2-{4-[(7-bromo-2-quinolinyl)oxy]phenoxy} propionic acid (SH80) against transplanted tumors in mice established in previous studies, require a (7-halo-2-quinoxalinoxy)- or a (7-halo-2-quinolinoxyl)-residue, respectively, bridged via a 1,4-OC6H4O-linker to C-2 of propionic acid. The present work demonstrates that substitution of fluorine at the 3-position of the 1,4-OC6H4O-linker of XK469 leads to a 10-fold reduction in activity, whereas the corresponding 2-fluoro analog proved to be 100-fold less active than XK469. Moreover, the latter tolerated substitution of but a single, additional methyl group to the 2-position of the propionic acid moiety, that is, the isobutyric acid analog, without loss of significant in vivo activity. Indeed, an intact 2-oxypropionic acid moiety is a prerequisite for maximum antitumor activity of 1a. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.011
• 作为产物：
  描述：

  methyl 2-(4-amino-2-fluorophenoxy)propionate 在 硫酸 、 sodium nitrite 、 copper(I) oxide 、 copper(II) nitrate 作用下， 以 水 为溶剂， 以80%的产率得到methyl 2-(2-fluoro-4-hydroxyphenoxy)propionate
  参考文献：
  名称：

  Synthetic modification of the 2-oxypropionic acid moiety in 2-{4-[(7-chloro-2-quinoxalinyl)oxy]phenoxy}propionic acid (XK469), and consequent antitumor effects. Part 4

  摘要：

  The criteria for the activity of 2-{4-[(7-chloro-2 -quinoxalinyl)oxy]phenoxy}propionic acid (XK469) and 2-{4-[(7-bromo-2-quinolinyl)oxy]phenoxy} propionic acid (SH80) against transplanted tumors in mice established in previous studies, require a (7-halo-2-quinoxalinoxy)- or a (7-halo-2-quinolinoxyl)-residue, respectively, bridged via a 1,4-OC6H4O-linker to C-2 of propionic acid. The present work demonstrates that substitution of fluorine at the 3-position of the 1,4-OC6H4O-linker of XK469 leads to a 10-fold reduction in activity, whereas the corresponding 2-fluoro analog proved to be 100-fold less active than XK469. Moreover, the latter tolerated substitution of but a single, additional methyl group to the 2-position of the propionic acid moiety, that is, the isobutyric acid analog, without loss of significant in vivo activity. Indeed, an intact 2-oxypropionic acid moiety is a prerequisite for maximum antitumor activity of 1a. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.011

文献信息

• Fluorophenoxy compounds, herbicidal compounds and processes
  申请人：THE DOW CHEMICAL COMPANY

  公开号：EP0304965A2

  公开（公告）日：1989-03-01

  Certain novel fluorophenoxy derivatives, in particular phenoxyfluorophenoxyaklanoic acids and derivatives thereof are described. These novel compounds bear 1 and 2 fluorine substituents on the phenyl group which is attached to the alkanoic acid group. These novel compounds exhibit surprising preemergent and postemergent activity when used according to the method of the invention in the control of grassy weeds.

  本文介绍了某些新型氟苯氧基衍生物，特别是苯氧基氟苯氧基烷酸及其衍生物。这些新型化合物在连接到烷酸基团的苯基上带有 1 个和 2 个氟取代基。当按照本发明的方法用于防治禾本科杂草时，这些新型化合物表现出惊人的芽前和芽后活性。
• Fluorophenoxy compounds, herbicidal compositions and methods
  申请人：THE DOW CHEMICAL COMPANY

  公开号：EP0142328B1

  公开（公告）日：1991-04-17
• ROGERS, RICHARD B.
  作者：ROGERS, RICHARD B.

  DOI：——

  日期：——
• US4750931A
  申请人：——

  公开号：US4750931A

  公开（公告）日：1988-06-14
• US4888050A
  申请人：——

  公开号：US4888050A

  公开（公告）日：1989-12-19