γ-methyl-α-phenyltetronic acid | 21053-95-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: γ-methyl-α-phenyltetronic acid
• 英文别名: α-Phenyl-β-hydroxy-γ-methyl-Δ^α,β-butenolide；4-Hydroxy-5-methyl-3-phenylfuran-2(5H)-one；3-hydroxy-2-methyl-4-phenyl-2H-furan-5-one
• CAS: 21053-95-2
• 化学式: C₁₁H₁₀O₃
• 分子量: 190.199
• InChiKey: CZYGYAPXRZQIJE-UHFFFAOYSA-N

物化性质

• 熔点：
  165 °C
• 沸点：
  387.6±42.0 °C(Predicted)
• 密度：
  1.296±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  γ-methyl-α-phenyltetronic acid 在 sodium methylate 、 potassium carbonate 、 三乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 生成 3-phenyl-7a-methyl-7,7a-dihydrofuran[3,2-d][1,2]oxathin-5,5-dioxide-2(4H)-one
  参考文献：
  名称：

  Synthesis and anti-BVDV activity of novel δ-sultones in vitro: Implications for HCV therapies

  摘要：

  In this study we report the synthesis and activity against bovine viral diarrhea virus (BVDV) of a novel series of bicycle delta-sultones containing gamma-lactones. BVDV is responsible for major losses in cattle. Some of the synthesized delta-sultones showed pronounced anti-BVDV activity with EC50 values of 0.12-1.0 mu M and no significant cytotoxicity. Among them, the ortho bromosubstituted derivative 4f (EC50 = 0.12 mu M) showed better antiviral activity than other derivatives and was 10 fold more that of than positive control ribavirin (EC50 = 1.3 mu M). BVDV is also considered to be a valuable surrogate for the hepatitis C virus (HCV) in antiviral drug studies. The above results provided a novel candidate for the development of anti-HCV agents. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.03.012
• 作为产物：
  描述：

  2-phenylacetoxy-propionic acid ethyl ester 在 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 γ-methyl-α-phenyltetronic acid
  参考文献：
  名称：

  Synthesis and anti-BVDV activity of novel δ-sultones in vitro: Implications for HCV therapies

  摘要：

  In this study we report the synthesis and activity against bovine viral diarrhea virus (BVDV) of a novel series of bicycle delta-sultones containing gamma-lactones. BVDV is responsible for major losses in cattle. Some of the synthesized delta-sultones showed pronounced anti-BVDV activity with EC50 values of 0.12-1.0 mu M and no significant cytotoxicity. Among them, the ortho bromosubstituted derivative 4f (EC50 = 0.12 mu M) showed better antiviral activity than other derivatives and was 10 fold more that of than positive control ribavirin (EC50 = 1.3 mu M). BVDV is also considered to be a valuable surrogate for the hepatitis C virus (HCV) in antiviral drug studies. The above results provided a novel candidate for the development of anti-HCV agents. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.03.012

文献信息

• Reaction of O-trimethylsilylated cyanohydrins with α-bromoesters: a new synthesis of tetronic acids
  作者：Larry R. Krepski、Laurie E. Lynch、Steven M. Heilmann、Jerald K. Rasmussen

  DOI：10.1016/s0040-4039(00)98491-0

  日期：1985.1

  Tetronic acids and β-keto-γ-butyrolactones are easily prepared by the zinc induced reaction of O-trimethylsilylated cyanohydrins and α-bromoesters.

  易位酸和β-酮-γ-丁内酯很容易通过锌诱导的O-三甲基甲硅烷基化氰醇与α-溴代酸酯反应制得。
• Caus, Maria J.; Cerfontain, Hans; Piniella, Juan F., Recueil des Travaux Chimiques des Pays-Bas, 1983, vol. 102, p. 515 - 519
  作者：Caus, Maria J.、Cerfontain, Hans、Piniella, Juan F.

  DOI：——

  日期：——
• KREPSKI, L. R.;LYNCH, L. E.;HEILMANN, S. M.;RASMUSSEN, J. K., TETRAHEDRON LETT., 1985, 26, N 8, 981-984
  作者：KREPSKI, L. R.、LYNCH, L. E.、HEILMANN, S. M.、RASMUSSEN, J. K.

  DOI：——

  日期：——
• Synthesis and anti-BVDV activity of novel δ-sultones in vitro: Implications for HCV therapies
  作者：Hai-Wei Xu、Ling-Jie Zhao、Huan-Fei Liu、Dan Zhao、Jiao Luo、Xiao-Ping Xie、Wen-Sheng Liu、Jia-Xin Zheng、Gui-Fu Dai、Hong-Min Liu、Long-Hua Liu、Yi-Bo Liang

  DOI：10.1016/j.bmcl.2014.03.012

  日期：2014.5

  In this study we report the synthesis and activity against bovine viral diarrhea virus (BVDV) of a novel series of bicycle delta-sultones containing gamma-lactones. BVDV is responsible for major losses in cattle. Some of the synthesized delta-sultones showed pronounced anti-BVDV activity with EC50 values of 0.12-1.0 mu M and no significant cytotoxicity. Among them, the ortho bromosubstituted derivative 4f (EC50 = 0.12 mu M) showed better antiviral activity than other derivatives and was 10 fold more that of than positive control ribavirin (EC50 = 1.3 mu M). BVDV is also considered to be a valuable surrogate for the hepatitis C virus (HCV) in antiviral drug studies. The above results provided a novel candidate for the development of anti-HCV agents. (C) 2014 Elsevier Ltd. All rights reserved.