5-(4-nitrophenyl)-dihydro-2(3H)-furanone | 10348-08-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(4-nitrophenyl)-dihydro-2(3H)-furanone
• 英文别名: 5-(4-nitrophenyl)dihydrofuran-2(3H)-one；5-(4-nitrophenyl)dihydrofuran-2(3H)-on；5-(4-nitro-phenyl)-dihydro-furan-2-one；4-hydroxy-4-(4-nitro-phenyl)-butyric acid-lactone；4-Hydroxy-4-(4-nitro-phenyl)-buttersaeure-lacton；γ-Nitrophenyl-γ-butyrolacton；5-(4-Nitrophenyl)oxolan-2-one
• CAS: 10348-08-0；112606-90-3；112709-18-9；112709-19-0
• 化学式: C₁₀H₉NO₄
• 分子量: 207.186
• InChiKey: XNDKJJDCVLCSBY-UHFFFAOYSA-N

物化性质

• 熔点：
  112-113 °C(Solv: chloroform (67-66-3); carbon tetrachloride (56-23-5))
• 沸点：
  426.3±45.0 °C(Predicted)
• 密度：
  1.360±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 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：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(4-nitrophenyl)-dihydro-2(3H)-furanone 生成 (5R)-5-(4-nitrophenyl)oxolan-2-one
  参考文献：
  名称：

  FRANCOTTE, ERIC;WOLF, ROMAIN M., CHIRALITY, 2,(1990) N, C. 16-31

  摘要：

  DOI：
• 作为产物：
  描述：

  (P-硝基苯基)环氧乙烷 在 sodium 作用下， 生成 5-(4-nitrophenyl)-dihydro-2(3H)-furanone
  参考文献：
  名称：

  Kayser, Margaret M.; Morand, Peter, Canadian Journal of Chemistry, 1980, vol. 58, # 3, p. 302 - 306

  摘要：

  DOI：

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。
• Nucleo-Palladation-Triggering Alkene Functionalization: A Route to γ-Lactones
  作者：Meifang Zheng、Pengquan Chen、Liangbin Huang、Wanqing Wu、Huanfeng Jiang

  DOI：10.1021/acs.orglett.7b02688

  日期：2017.11.3

  An unprecedented strategy for the highly effective synthesis of gamma-lactones from homoallylic alcohols was achieved by palladium catalysis in one step. The protocol affords aryl, alkyl, and spiro gamma-lactones directly from readily available "homoallylic alcohols in good yields with excellent functional group tolerance and high chemoselectivity under mild conditions.
• Direct Lactone Formation by Using Hypervalent Iodine(III) Reagents with KBr via Selective C−H Abstraction Protocol
  作者：Toshifumi Dohi、Naoko Takenaga、Akihiro Goto、Akinobu Maruyama、Yasuyuki Kita

  DOI：10.1021/ol071315n

  日期：2007.8.1

  [GRAPHICS]We have developed a new and reliable method for the direct construction of biologically important aryl lactones and phthalides from carboxylic and benzoic acids, using a combination of hypervalent iodine(III) reagents with KBr.
• Synthesis of Lactones via C–H Functionalization of Nonactivated C(sp³)–H Bonds
  作者：Johannes Richers、Michael Heilmann、Markus Drees、Konrad Tiefenbacher

  DOI：10.1021/acs.orglett.6b03371

  日期：2016.12.16

  An electron-deficient amide is utilized as a directing group to functionalize nonactivated C(sp(3))-H bonds through radical 1,5-hydrogen abstraction. The gamma-bromoamides formed are subsequently converted to gamma-lactones under mild conditions. The method described is not limited to tertiary and secondary positions but also allows functionalization of primary nonactivated sp(3)-hybridized positions in a one-pot sequence. In addition, the broad functional group tolerance renders this method suitable for the late-stage introduction of gamma-lactones into complex carbon frameworks.
• A New Synthesis of γ-Butyrolactones via AuCl₃- or Hg(II)-Catalyzed Intramolecular Hydroalkoxylation of 4-Bromo-3-yn-1-ols
  作者：Maddi Sridhar Reddy、Yalla Kiran Kumar、Nuligonda Thirupathi

  DOI：10.1021/ol2033493

  日期：2012.2.3

  An efficient conversion of 4-bromo-3-yn-1-ols to gamma-butyrolactones via AuCl3-catalyzed electrophilic cyclization (hydroxyl-assisted regioselective hydration) in wet toluene is described. Various secondary and tertiary alcohols including benzylic systems were found to be equally reactive with moderate to excellent yields obtained in all cases.