4,5,5-triphenyldihydrofuran-2(3H)-one | 57697-68-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 4,5,5-triphenyldihydrofuran-2(3H)-one
• 英文别名: 4,5,5-triphenyl-dihydro-furan-2-one；4,5,5-Triphenyl-dihydro-furan-2-on；2(3H)-Furanone, dihydro-4,5,5-triphenyl-；4,5,5-triphenyloxolan-2-one
• CAS: 57697-68-4
• 化学式: C₂₂H₁₈O₂
• 分子量: 314.384
• InChiKey: JJYXDDLDDNDXIU-UHFFFAOYSA-N

物化性质

• 熔点：
  162.5-163.5 °C
• 沸点：
  469.5±45.0 °C(Predicted)
• 密度：
  1.176±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  4,5,5-triphenyldihydrofuran-2(3H)-one 、 氢碘酸 生成 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  Purdie; Arup, Journal of the Chemical Society, 1910, vol. 97, p. 1542

  摘要：

  DOI：
• 作为产物：
  描述：

  4,5,5-Triphenyl-tetrahydro-furan-2-ol 在 silver carbonate 作用下， 以 甲苯 为溶剂， 以67%的产率得到4,5,5-triphenyldihydrofuran-2(3H)-one
  参考文献：
  名称：

  Diastereoselective Synthesis of Highly Substituted Five-Membered-Ring Oxygen Heterocycles by Zirconocene-Mediated C-C Coupling Reactions

  摘要：

  As homoenolate equivalents, zirconocene-1-aza-1,3-diene complexes were used for the first time in stereoselective synthesis. By insertion of an unsymmetrical ketone in the Zr-C σ bond, sterically demanding trisubstituted dihydro- and tetrahydrofuran derivatives were prepared in good overall yields and with high diastereoselectivities (see below).

  DOI：

  10.1002/(sici)1521-3773(19980703)37:12<1673::aid-anie1673>3.0.co;2-a

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。
• Electroreductive coupling of aromatic ketones, aldehydes, and aldimines with α,β-unsaturated esters: Synthesis of 5-aryl substituted γ-butyrolactones and lactams
  作者：Naoki Kise、Yusuke Hamada、Toshihiko Sakurai

  DOI：10.1016/j.tet.2017.01.013

  日期：2017.2

  The electroreductive intermolecular coupling of aromatic ketones and aldehydes with α,β-unsaturated esters in the presence of TMSCl gave the adducts as γ-trimethylsiloxy esters. The detrimethylsilylation of the adducts with TBAF afforded 5-aryl substituted γ-butyrolactones. The electroreductive coupling of N-(4-methoxyphenyl)-1-arylmethaneimines with methyl acrylate in the presence of TMSCl gave the

  在TMCSC1存在下，芳族酮和醛与α，β-不饱和酯的电还原分子间偶联产生加合物，为γ-三甲基甲硅烷氧基酯。用TBAF将加合物的三甲基甲硅烷基化得到5-芳基取代的γ-丁内酯。N的电耦合-（4-甲氧基苯基）-1-芳基亚甲基与TMSCl存在下的丙烯酸甲酯得到加合物，为4-芳基-4-（（4-甲氧基苯基）氨基）丁酸甲酯。通过用NaH环化并随后用CAN氧化，将加合物转化为5-芳基-γ-丁内酰胺。通过该方法由烟醛制备（±）-烟碱。在TMCSC1存在下，芳族酮和醛亚胺与丙烯腈的电还原偶联分别得到4-芳基-4-（三甲基甲硅烷氧基）丁腈和4-芳基-4-（（4-甲氧基苯基）氨基）丁腈。
• Direct generation of lithium homoenolates from 3-aryl α,β-unsaturated ketones or esters by an arene-catalysed lithiation: Synthesis of substituted tetrahydrofurans and γ-butyrolactones
  作者：Emma Alonso、Diego J. Ramón、Miguel Yus

  DOI：10.1016/s0040-4020(96)01155-6

  日期：1997.2

  The reaction of α,β-unsaturated ketones 1 with an excess of lithium powder, a catalytic amount of naphthalene (4 %) and different carbonyl compounds in the presence of boron trifluoride in THF at −78 – 0°C yields, after treatament with silyl nucleophile and final hydrolysis, the expected substituted tetrahydrofurans 5. Similar methodology applied to β-aryl acrylic esters 6, but without using boron trifluoride

  α-β-不饱和酮1与过量的锂粉，催化量的萘（4％）和不同的羰基化合物在三氟化硼存在下于THF中在-78 – 0°C下反应，用•甲硅烷基亲核试剂和最终水解，预期取代的四氢呋喃5。将类似的方法应用于β-芳基丙烯酸酯6，但不使用三氟化硼或甲硅烷基试剂，则可得到相应的内酯7。
• The Reaction of Olefins with Malonic Acid in the Presence of Manganese(III) Acetate
  作者：Nobuyuki Ito、Hiroshi Nishino、Kazu Kurosawa

  DOI：10.1246/bcsj.56.3527

  日期：1983.11

  The reaction of 1,1-diphenylethene with malonic acid in the presence of manganese(III) acetate gave 3,3,8,8-tetraphenyl-2,7-dioxaspiro[4.4]nonane-1,6-dione and 4,4-diphenyl-2-(2,2-diphenylethenyl)-4-butanolide. Similar reactions with 1,1-bis(4-methoxyphenyl)ethene, methylenecyclohexane, 2-phenylpropene, 1-octene, and cyclohexene yielded the corresponding 2,7-dioxaspiro[4.4]nonane-1,6-diones.

  在乙酸锰 (III) 存在下，1,1-二苯基乙烯与丙二酸反应得到 3,3,8,8-四苯基-2,7-二氧杂螺[4.4]壬烷-1,6-二酮和 4,4 -二苯基-2-(2,2-二苯基乙烯基)-4-丁内酯。与 1,1-双（4-甲氧基苯基）乙烯、亚甲基环己烷、2-苯基丙烯、1-辛烯和环己烯的类似反应产生相应的 2,7-二氧杂螺[4.4]壬烷-1,6-二酮。
• Oxidative Ring-Opening Reaction of Cyclopropanone Acetals with Carbonyl Compounds via Photoinduced Electron Transfer. Generation of a .beta.-Carbonyl Radical Species and Its Application to the Synthesis of .gamma.-Hydroxy Ester Derivatives
  作者：Manabu Abe、Akira Oku

  DOI：10.1021/jo00115a022

  日期：1995.5

  Photoinduced electron transfer (PET) reactions of 2-substituted or 2,2-disubstituted cyclopropanone methyl trialkylsilyl acetals 1a-e,g and 1-siloxy-2-oxabicyclo[3.1.0]hexane (1f) with carbonyl compounds 2 (benzophenone (2a), acetophenone (2b), 2-acetonaphthone (2c), 2-acetylpyridine (2d), 4-acetylbenzonitrile (2e), 2,3-butanedione (2f), and benzoyl cyanide (2g)) were examined in the presence of Mg(ClO4)(2). Carbon-carbon bond coupling products (gamma-hydroxy esters 3 or their derivative butyrolactones 4) between 1 and 2 were formed in good yields. A mechanism is proposed for the product formation which is initiated by the single electron transfer (SET) from 1 to the excited state of 2. The SET generates a transient pair of ion radicals, i.e. a ring-opened sec- or tert-beta-carbonyl radical from 1 and a ketyl radical ion from 2 stabilized by the Mg salt. This realizes a novel type of carbon-carbon bond formation at the sterically crowded beta-position of propanoates.