5-phenethyldihydrofuran-2(3H)-one | 112606-95-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 5-phenethyldihydrofuran-2(3H)-one
• 英文别名: 2(3H)-Furanone, dihydro-5-(2-phenylethyl)-；5-(2-phenylethyl)oxolan-2-one
• CAS: 112606-95-8
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: ONECXZFGYJSVIF-UHFFFAOYSA-N

物化性质

• 沸点：
  173-175 °C(Press: 7 Torr)
• 密度：
  1.090±0.06 g/cm3(Predicted)
• 熔点：
  <25 °C

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-phenethyldihydrofuran-2(3H)-one 在 氯化亚砜 、 zinc(II) chloride 作用下， 反应 24.0h， 生成
  参考文献：
  名称：

  Catalytic Asymmetric γ-Alkylation of Carbonyl Compounds via Stereoconvergent Suzuki Cross-Couplings

  摘要：

  With the aid of a chiral nickel catalyst, enantioselective gamma- (and delta-) alkylations of carbonyl compounds can be achieved through the coupling of gamma-haloamides with alkylboranes. In addition to primary alkyl nucleophiles, for the first time for an asymmetric cross-coupling of an unactivated alkyl electrophile, an arylmetal, a boronate ester, and a secondary (cyclopropyl) alkylmetal compound are shown to couple with significant enantioselectivity. A mechanistic study indicates that cleavage of the carbon-halogen bond of the electrophile is irreversible under the conditions for asymmetric carbon-carbon bond formation.

  DOI：

  10.1021/ja2079515
• 作为产物：
  描述：

  1-phenylhex-5-yn-3-ol 在 甲烷磺酸 、 C₂₁H₁₂F₉P*C₈H₁₈NO₄S₂^(1-)*Au⁽¹⁺⁾ 、 间氯过氧苯甲酸 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 5.0h， 以86%的产率得到5-phenethyldihydrofuran-2(3H)-one
  参考文献：
  名称：

  金催化串联环化/氧化有效合成γ-内酯

  摘要：

  开发了一种新型的Au催化的炔丙基醇串联环异构化/氧化反应。利用这种策略可以很容易地获得各种γ-内酯。值得注意的是，该反应的机理与提出钌亚乙烯基中间体的相关Ru催化的反应明显不同。

  DOI：

  10.1021/ol302323a

文献信息

• MnO₂-promoted carboesterification of alkenes with anhydrides: a facile approach to γ-lactones
  作者：Lihuan Wu、Zhenming Zhang、Jianhua Liao、Jianxiao Li、Wanqing Wu、Huanfeng Jiang

  DOI：10.1039/c5cc08867d

  日期：——

  A new radical cyclization method for the formation of C(sp³)–C(sp³) and C–O bonds via MnO₂-promoted alkene carboesterification with anhydrides is developed.

  一种新的基于锰促进的烯烃碳酯化反应的C(sp3)-C(sp3)和C-O键的放射状环化方法被开发出来。
• Gallium-catalyzed reductive lactonization of γ-keto acids with a hydrosilane
  作者：Norio Sakai、Shuhei Horikawa、Yohei Ogiwara

  DOI：10.1039/c6ra19286f

  日期：——

  Described herein is the GaCl3-catalyzed lactonization of γ-keto carboxylic acids in the presence of PhSiH3 leading to the direct preparation of γ-lactone derivatives. This reducing system showed a relatively wide functional group tolerance.

  本文描述了在PhSiH 3存在下GaCl 3催化的γ-酮羧酸的内酯化，从而直接制备γ-内酯衍生物。该还原体系显示出相对宽泛的官能团耐受性。
• Indium-Catalyzed Direct Conversion of Lactones into Thiolactones and Selenolactones in the Presence of Elemental Sulfur and Selenium
  作者：Norio Sakai、Shuhei Horikawa、Yohei Ogiwara

  DOI：10.1055/s-0036-1591849

  日期：2018.2

  Abstract The direct conversion of lactones into thiolactones with elemental sulfur (S8) catalyzed by InCl3/PhSiH3 in a one-pot reaction is described. This catalytic system was successfully applied to the novel preparation of selenolactones from lactones and selenium. The direct conversion of lactones into thiolactones with elemental sulfur (S8) catalyzed by InCl3/PhSiH3 in a one-pot reaction is described

  摘要 描述了一锅反应中InCl 3 / PhSiH 3催化用元素硫（S 8）将内酯直接转化为硫代内酯。该催化体系已成功应用于内酯和硒的硒代内酯的新型制备。 描述了一锅反应中InCl 3 / PhSiH 3催化用元素硫（S 8）将内酯直接转化为硫代内酯。该催化体系已成功应用于内酯和硒的硒代内酯的新型制备。
• Efficient Synthesis of γ‐Lactones by Cobalt‐Catalyzed Carbonylative Ring Expansion of Oxetanes under Syngas Atmosphere
  作者：Yitian Tang、Chaoren Shen、Qiyi Yao、Xinxin Tian、Bo Wang、Kaiwu Dong

  DOI：10.1002/cctc.202001294

  日期：2020.12.4

  A practical route from oxetane or thietane to γ‐(thio)butyrolactone via solvated‐proton‐assisted cobalt‐catalyzed carbonylative ring expansion under syngas atmosphere has been established. A wide variety of γ‐(thio)butyrolactones can be afforded in good to excellent yields. The versatility of this method has been well demonstrated in the synthesis of intermediates towards the natural product Arctigenin

  建立了在合成气气氛下通过溶剂化的质子辅助的钴催化的羰基化环膨胀从氧杂环丁烷或硫杂环丁烷生成γ-（硫代）丁内酯的实用路线。可以提供种类繁多的γ-（硫代）丁内酯，收率非常好。该方法的多功能性已在针对天然产物牛黄菌素以及药物巴氯芬和孟鲁司特的中间体的合成中得到了充分证明。已合理解释了观察到的乙二醇醚溶剂的促进作用。
• Photocatalytic Synthesis of γ-Lactones from Alkenes: High-Resolution Mass Spectrometry as a Tool To Study Photoredox Reactions
  作者：Ierasia Triandafillidi、Maroula G. Kokotou、Christoforos G. Kokotos

  DOI：10.1021/acs.orglett.7b03256

  日期：2018.1.5

  A mild photocatalytic manifold for the synthesis of γ-lactones has been developed. Utilizing Ru(bpy)3Cl2 as the photocatalyst, a cheap and reproducible synthetic protocol for γ-lactones has been introduced. Mechanistic studies revealed the successful monitoring of photocatalytic reactions and radical intermediates via high-resolution mass spectrometry.

  已经开发了用于合成γ-内酯的温和光催化歧管。利用Ru（bpy）3 Cl 2作为光催化剂，已经引入了廉价且可重现的γ-内酯合成方案。机理研究表明，通过高分辨率质谱已成功监测了光催化反应和自由基中间体。

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