3-苄基二氢-2,5-呋喃二酮 | 22884-81-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 中文名称: 3-苄基二氢-2,5-呋喃二酮
• 英文名称: 3-benzyltetrahydrofuran-2,4-dione
• 英文别名: 3-benzyl-furan-2,4-dione；2-Benzyl-4-hydroxy-acetessigsaeure-lacton；3-benzyl-2,4(3H,5H)-furandione；3-Benzyl-2,4-dioxotetrahydrofuran；2,4(3H,5H)-Furandione, 3-benzyl-；3-benzyloxolane-2,4-dione
• CAS: 22884-81-7
• 化学式: C₁₁H₁₀O₃
• 分子量: 190.199
• InChiKey: VHZXIZCTSXDLJY-UHFFFAOYSA-N

物化性质

• 熔点：
  167-169 °C
• 沸点：
  394.9±35.0 °C(Predicted)
• 密度：
  1.259±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2932190090

反应信息

• 作为反应物：
  描述：

  3-苄基二氢-2,5-呋喃二酮 在 氨 、 sodium nitrite 作用下， 生成 2-hydroxyimino-3-phenyl-propionic acid amide
  参考文献：
  名称：

  Wolff, Justus Liebigs Annalen der Chemie, 1913, vol. 399, p. 311

  摘要：

  DOI：
• 作为产物：
  描述：

  2-苄基乙酰乙酸乙酯 在 氯仿 、 溴 作用下， 生成 3-苄基二氢-2,5-呋喃二酮
  参考文献：
  名称：

  [四元酸衍生物。I.3-苄基四氢苯甲酸的一些衍生物]。

  摘要：

  DOI：

  10.1002/ardp.19582910210

文献信息

• The acid catalyzed cyclization of diazoketones: Preparation of 2,4(3H,5H) furandiones
  作者：R.D Miller、W Theis

  DOI：10.1016/s0040-4039(00)95905-7

  日期：1987.1

  Diazoketones derived from substituted ethyl hydrogen malonates produced by the selective hydrolysis of the corresponding malonate esters cyclize in the presence of catalytic amounts of boron trifluoride etherate in methanol to yield 2,4(3H,5H) furandiones. The cyclic keto orthoesters appear to be intermediates in the reaction.

  通过在甲醇中催化量的三氟化硼醚化物的存在下，由相应的丙二酸酯的选择性水解产生的由取代的丙二酸氢乙酯生成的重氮酮环化，生成2,4（3H，5H）呋喃二酮。环状酮基原酸酯似乎是反应中的中间体。
• Method for reducing a susceptibility to tumor formation induced by 3-deoxyglucosone and precursors thereof
  申请人：Brown R. Truman

  公开号：US20060089316A1

  公开（公告）日：2006-04-27

  Disclosed are methods of using various compounds, which are known to bind to 3-deoxyglucosone (3DG) or precursors thereof, in order to reduce a susceptibility to tumor formation and/or to prevent or delay onset of tumor formation induced by 3DG and its precursors. Also disclosed is the reduction of 3DG levels in high fructose corn syrop so that the high fructose corn syrup is less likely to induce tumor formation.

  公开了使用各种已知与3-脱氧葡萄糖酮（3DG）或其前体结合的化合物的方法，以减少对肿瘤形成的易感性和/或预防或延迟由3DG及其前体诱导的肿瘤形成。还公开了降低高果糖玉米糖浆中3DG水平的方法，以使高果糖玉米糖浆不太可能诱导肿瘤形成。
• Calam et al., Biochemical Journal, 1949, vol. 45, p. 520,522
  作者：Calam et al.

  DOI：——

  日期：——
• Chemoselective reduction of 3-arylmethylidenetetrahydrofuran-2,4-diones with triethylsilane and sodium cyanotrihydridoborate in acid media
  作者：F. S. Pashkovskii、E. M. Shchukina、F. A. Lakhvich

  DOI：10.1134/s1070428009060098

  日期：2009.6

  3-Arylmethylidenetetrahydrofuran-2,4-diones were smoothly reduced to the corresponding 3-benzyl derivatives in 50-98% yield with triethylsilane in trifluoroacetic acid or with sodium cyanotrihydridoborate in the system tetrahydrofuran-2 N hydrochloric acid. The reduction of 3-(3-arylprop-2-en-1-ylidene)-tetrahydrofuran-2,4-diones with sodium cyanotrihydridoborate gave 3-cinnamyltetrahydrofuran-2,4-diones as the only products.
• α-((Tetronoyl)oxy)- and α-((tetramoyl)oxy)methyl ketone inhibitors of the interleukin-1β converting enzyme (ICE)
  作者：Todd L. Graybill、Catherine P. Prouty、Gary J. Speier、Denton Hoyer、Roland E. Dolle、Carla T. Helaszek、Mark A. Ator、Joanne Uhl、Joost Strastes

  DOI：10.1016/s0960-894x(96)00574-4

  日期：1997.1

  Aryl-substituted tetronic acids, tetramic acids, and cyclic beta-dicarbonyl moieties were evaluated as leaving groups in the peptidyl-COCH2-X type inhibitor iii. Tripeptidyl aspartyl alpha-((tetronoyl)oxy)- and alpha-((tetramoyl)oxy)methyl ketone derivatives demonstrate potent time-dependent inhibition (k(obs)/[T] 100,000-250,000 M(-1)s(-1)) of the cysteine protease ICE. Copyright (C) 1996 Elsevier Science Ltd