4-Ethoxy-5-phenyl-cyclopent-4-en-1,3-dion | 91680-95-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-Ethoxy-5-phenyl-cyclopent-4-en-1,3-dion
• 英文别名: 4-ethoxy-5-phenyl-4-cyclopentene-1,3-dione；4-Ethoxy-5-phenylcyclopent-4-ene-1,3-dione
• CAS: 91680-95-4
• 化学式: C₁₃H₁₂O₃
• 分子量: 216.236
• InChiKey: BUWGFVUCFIEIFN-UHFFFAOYSA-N

物化性质

• 熔点：
  59 °C
• 沸点：
  369.3±42.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-Ethoxy-5-phenyl-cyclopent-4-en-1,3-dion 在 哌啶 、 盐酸 、 sodium phosphate 作用下， 以 氯仿 为溶剂， 反应 16.5h， 生成 2-Diphenylethyliden-4-hydroxy-5-phenyl-cyclopent-4-en-1,3-dion
  参考文献：
  名称：

  抗凝剂芳烷基和芳基亚烷基环戊-4-烯-1,3-二酮

  摘要：

  使用六种标题化合物中的两种，对大鼠单次口服给药后 (165-330 毫克/千克) 凝血酶原水平可以达到低于标准的 15%。合适的氧代烷基环戊烯二酮可以环化为 1H -茚 - 1,5 (6H) - 二酮 6a 或 7,7a - 二氢 - 1H - 茚酮 6b。两者都是强抗凝剂。

  DOI：

  10.1002/ardp.19843170910
• 作为产物：
  描述：

  (2-ethoxy-1-hydroxy-4-oxo-3-phenyl-2-cyclobutenyl)acetic acid 在 1-氧化-2-巯基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以32%的产率得到4-Ethoxy-5-phenyl-cyclopent-4-en-1,3-dion
  参考文献：
  名称：

  Radical-mediated ring enlargement of cyclobutenones: new synthetic potential of squaric acid.

  摘要：

  4-Hydroxy-2-cyclobutenones, which are readily obtainable from diethyl squarate, reacted with lead tetraacetate to give 5-acetoxy-2(5H)-furanones and 5-alkylidene-2(5H)-furanones via oxy-radical-triggered ring opening (beta-scission) and subsequent 5-endo reclosure. This method was extended to saturated four-membered alpha-ketol and applied to the synthesis of a natural product (Z-isomer of multicolanate). A carbon-centered radical-triggered reaction was also performed in which photolysis of a mixed anhydride of thiohydroxamic acid and (4-oxo-2-cyclobutenyl)acetic acid afforded a 4-cyclopentene-1,3-dione rather than the furanone as a rearranged product. The similarity of these rearrangements is discussed using a PM3 calculation in terms of pentadienoyl radical to cyclopentenone radical cyclization and its oxa version.

  DOI：

  10.1021/ja00143a006

文献信息

• Ring Expansion of Diazo-Functionalized 4-Hydroxycyclobutenone:  Catalytic Ring Opening and Recyclization to 2(5<i>H</i>)-Furanone/Cyclopentenedione and Thermal 4π−8π Electrocyclic Ring Opening−Closure to Diazepinedione
  作者：Masatomi Ohno、Masashi Noda、Yoshihiko Yamamoto、Shoji Eguchi

  DOI：10.1021/jo980523d

  日期：1999.2.1

  cyclopentene-1,3-dione via an alpha-carbocation intermediate and a carbenoid (carbene) intermediate, respectively. Thermal rearrangement of some of these compounds led to the formation of diazepinediones without the extrusion of nitrogen through tandem 4pi electrocyclic ring opening and 8pi electrocyclic ring closure processes.

  在C-4处带有重氮基团的4-羟基环丁烯酮经酸催化和Rh催化（也光催化）分解，通过α-羰基化中间体和a生成2（5H）-呋喃酮和/或环戊烯-1,3-二酮。类胡萝卜素（卡宾）中间体。其中一些化合物的热重排导致二氮杂二酮的形成而没有通过串联的4pi电动开环和8pi电动闭环过程挤出氮气。
• REHSE, K.;LEHMKE, J., ARCH. PHARM., 1984, 317, N 9, 781-789
  作者：REHSE, K.、LEHMKE, J.

  DOI：——

  日期：——
• Radical-mediated ring enlargement of cyclobutenones: new synthetic potential of squaric acid.
  作者：Yoshihiko Yamamoto、Masatomi Ohno、Shoji Eguchi

  DOI：10.1021/ja00143a006

  日期：1995.9

  4-Hydroxy-2-cyclobutenones, which are readily obtainable from diethyl squarate, reacted with lead tetraacetate to give 5-acetoxy-2(5H)-furanones and 5-alkylidene-2(5H)-furanones via oxy-radical-triggered ring opening (beta-scission) and subsequent 5-endo reclosure. This method was extended to saturated four-membered alpha-ketol and applied to the synthesis of a natural product (Z-isomer of multicolanate). A carbon-centered radical-triggered reaction was also performed in which photolysis of a mixed anhydride of thiohydroxamic acid and (4-oxo-2-cyclobutenyl)acetic acid afforded a 4-cyclopentene-1,3-dione rather than the furanone as a rearranged product. The similarity of these rearrangements is discussed using a PM3 calculation in terms of pentadienoyl radical to cyclopentenone radical cyclization and its oxa version.
• Anticoagulante Arylalkyl- und Arylalkyliden-cyclopent-4-en-1,3-dione
  作者：Klaus Rehse、Josefa Lehmke

  DOI：10.1002/ardp.19843170910

  日期：——

  Mit zwei von sechs Titelverbindungen konnte nach einmaliger oraler Verabreichung an Ratten (165–330 mg/kg) Prothrombinspiegel von weniger als 15% der Norm erzielt werden. Geeignete Oxoalkylcyclopentendione konnten zum 1H‐Inden‐1,5(6H)‐dion 6a bzw. 7,7a‐Dihydro‐1H‐indenon 6b cyclisiert werden. Beide sind stark anticoagulant wirksam.

  使用六种标题化合物中的两种，对大鼠单次口服给药后 (165-330 毫克/千克) 凝血酶原水平可以达到低于标准的 15%。合适的氧代烷基环戊烯二酮可以环化为 1H -茚 - 1,5 (6H) - 二酮 6a 或 7,7a - 二氢 - 1H - 茚酮 6b。两者都是强抗凝剂。