5-phenyl-3-oxo-tetrahydrofuran | 99875-61-3

• 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: 5-phenyl-3-oxo-tetrahydrofuran
• 英文别名: 5-phenyl-3-tetrahydrofuranone；5-phenyltetrahydrofuran-3-one；5-phenyldihydrofuran-3-one；2-phenyltetrahydrofuran-4-one；5-Phenyloxolan-3-one
• CAS: 99875-61-3
• 化学式: C₁₀H₁₀O₂
• 分子量: 162.188
• InChiKey: JQLBLPDNRKSRDY-UHFFFAOYSA-N

物化性质

• 熔点：
  106-107 °C
• 沸点：
  293.4±35.0 °C(Predicted)
• 密度：
  1.154±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  Tert-butyl 2-diazo-5-hydroxy-3-oxo-5-phenylpentanoate 在 dirhodium tetraacetate 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙腈 、 苯 为溶剂， 反应 11.25h， 生成 5-phenyl-3-oxo-tetrahydrofuran
  参考文献：
  名称：

  Aldol-cyclization reaction sequence for the synthesis of tetrahydrofurans

  摘要：

  The aldol reactions of alpha-diazo-beta-ketoesters with a variety of aldehydes produced adducts which underwent Rh(II)-catalyzed O-H insertion reaction to yield highly substituted tetrahydrofurans. Alkylation and decarboxylation of these tetrahydrofurans formed a wide variety of tetrahydrofuran structures. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00766-1

文献信息

• Transformation of homoallylic alcohol oxides into 3-hydroxytetrahydrofurans in aqueous HClO4
  作者：M. V. Chirskaya、A. A. Vasil’ev、S. V. Shorshnev、S. I. Sviridov

  DOI：10.1007/s11172-006-0415-8

  日期：2006.7

  Hydrolysis of allyl carbinol oxides in aqueous HClO4 gave the corresponding 1,2,4-triols. On heating in the same reaction medium, they underwent cyclization into 3-hydroxytetrahydrofurans. The method is restricted to substrates that can generate stable carbocations via elimination of the hydroxy group from position 4 in intermediate 1,2,4-triols.

  烯丙基甲醇氧化物在 HClO4 水溶液中水解得到相应的 1,2,4-三醇。在相同的反应介质中加热时，它们环化成 3-羟基四氢呋喃。该方法仅限于可通过消除中间体 1,2,4-三醇中 4 位羟基而产生稳定碳正离子的底物。
• Rhodium carbenoid mediated cyclisation of α-diazo-β-keto-δ-hydroxy-phenylsulfones
  作者：Fabienne Lacrampe、Françoise Léost、Alain Doutheau

  DOI：10.1016/s0040-4039(00)00724-3

  日期：2000.6

  The title reaction give rise to 2-phenylsulfonyl-3-oxo-tetrahydrofurans in satisfactory yields providing an entry to some furan derivatives.

  标题反应以令人满意的产率产生2-苯基磺酰基-3-氧代-四氢呋喃，提供了一些呋喃衍生物的入口。
• A remarkable ene-like reaction: Development and synthetic applications
  作者：Marco A. Ciufolini、Melissa V. Deaton、Shuren Zhu、Mingying Chen

  DOI：10.1016/s0040-4020(97)01016-8

  日期：1997.12

  A catalytic ene-like reaction of aldehydes with those vinyl ethers that display the oxygen functionality at the central carbon of an allylic system, e.g., 2-methoxypropene, is discussed in detail. The reaction is promoted by 0.05 eguiv. of the 1:1 complex of Yb(fod)(3) and acetic acid, and it is forms the centerpiece of our synthesis of chlorovulone II, mitomycinoids and phyllanthocin. (C) 1997 Elsevier Science Ltd.
• Ye, Longwu; Cui, Li; Zhang, Guozhu, Journal of the American Chemical Society, 2010, vol. 132, p. 3258 - 3259
  作者：Ye, Longwu、Cui, Li、Zhang, Guozhu、Zhang, Liming

  DOI：——

  日期：——
• LIPOXYGENASE-INHIBITING HYDROXAMIC ACID AND N-HYDROXYUREA DERIVATIVES
  申请人：PFIZER INC.

  公开号：EP0570401B1

  公开（公告）日：1994-11-09