3-(4-benzyloxyphenoxy)dihydrofuran-2-one | 444068-96-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(4-benzyloxyphenoxy)dihydrofuran-2-one
• 英文别名: 3-(4-benzyloxyphenoxy)butyrolactone；3-(4-Phenylmethoxyphenoxy)oxolan-2-one
• CAS: 444068-96-6
• 化学式: C₁₇H₁₆O₄
• 分子量: 284.312
• InChiKey: BSUPKHJOTUEACU-UHFFFAOYSA-N

物化性质

• 熔点：
  113-115 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  490.0±40.0 °C(Predicted)
• 密度：
  1.233±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-benzyloxyphenoxy)dihydrofuran-2-one 在 palladium on activated charcoal 盐酸 、 氢气 、 potassium carbonate 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 反应 10.0h， 生成 3-{4-[(7-chloro-2-quinoxalinyl)oxy]phenoxy}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
• 作为产物：
  描述：

  α-溴-γ-丁内酯 、 4-苄氧基苯酚 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以72%的产率得到3-(4-benzyloxyphenoxy)dihydrofuran-2-one
  参考文献：
  名称：

  评估使用碘化sa裂解的新连接子系统。在羰基化合物的固相合成中的应用。

  摘要：

  已开发出一种用于固相合成的新连接子设计，该设计在温和的中性条件下使用碘化sa（II）进行裂解。使用氧连接剂在酮和酰胺的固相合成中已经说明了连接剂方法的可行性。描述了对碘化II（II）裂解反应机理的见解，并评估了顺序裂解碳-碳键形成过程的潜力。

  DOI：

  10.1039/b506294b

文献信息

• Reduction of α-aryloxy carbonyl compounds with samarium(ii) iodide. A new traceless linker for the solid phase synthesis of carbonyl compounds
  作者：Fiona McKerlie、David J. Procter、Graham Wynne

  DOI：10.1039/b200365c

  日期：2002.3.7

  A new linker for the solid phase synthesis of functionalised carbonyl compounds which is cleaved under mild, neutral conditions using samarium(II) iodide has been developed; the manipulation of an immobilised γ-butyrolactone has been carried out to illustrate the utility of the linker.

  一种用于固相合成功能化羰基化合物的新连接剂已被开发，该连接剂在温和中性条件下使用二碘化钐（Samarium(II) iodide）断裂。通过操作固定化的γ-丁内酯，展示了该连接剂的实用性。
• Evaluation of a new linker system cleaved using samarium(ii) iodide. Application in the solid phase synthesis of carbonyl compounds
  作者：Fiona McKerlie、Iain M. Rudkin、Graham Wynne、David J. Procter

  DOI：10.1039/b506294b

  日期：——

  A new linker design for solid phase synthesis has been developed that is cleaved under mild, neutral conditions using samarium(II) iodide. The feasibility of the linker approach has been illustrated in the solid phase synthesis of ketones and amides using an oxygen linker. Insights into the mechanism of the samarium(II) iodide cleavage reaction are described and the potential of a sequential cleavage

  已开发出一种用于固相合成的新连接子设计，该设计在温和的中性条件下使用碘化sa（II）进行裂解。使用氧连接剂在酮和酰胺的固相合成中已经说明了连接剂方法的可行性。描述了对碘化II（II）裂解反应机理的见解，并评估了顺序裂解碳-碳键形成过程的潜力。
• 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.