3-(4-hydroxyphenoxy)butyrolactone | 857903-48-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-(4-hydroxyphenoxy)butyrolactone
• 英文别名: 3-(4-hydroxyphenoxy)oxolan-2-one
• CAS: 857903-48-1
• 化学式: C₁₀H₁₀O₄
• 分子量: 194.187
• InChiKey: WLPLXVQHDAKKHD-UHFFFAOYSA-N

物化性质

• 熔点：
  96-97 °C
• 沸点：
  438.4±35.0 °C(Predicted)
• 密度：
  1.346±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.09
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-(4-hydroxyphenoxy)butyrolactone 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)-phenoxy]-4-hydroxy-butyric 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：

  4-苄氧基苯酚 在 palladium on activated charcoal 盐酸 、 potassium fluoride 、 氢气 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 反应 6.0h， 生成 3-(4-hydroxyphenoxy)butyrolactone
  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

• 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
  作者：Stuart T. Hazeldine、Lisa Polin、Juiwanna Kushner、Kathryn White、Thomas H. Corbett、Jerome P. Horwitz

  DOI：10.1016/j.bmc.2005.04.011

  日期：2005.6

  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.