3-甲基-4-苯基-二氢-呋喃-2-酮 | 10606-45-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 中文名称: 3-甲基-4-苯基-二氢-呋喃-2-酮
• 英文名称: α-Methyl-β-phenyl-γ-butyrolacton
• 英文别名: 3-methyl-4-phenyl-dihydro-furan-2-one；3-Methyl-4-phenyl-dihydro-furan-2-on；3-Methyl-4-phenyloxolan-2-one
• CAS: 10606-45-8
• 化学式: C₁₁H₁₂O₂
• 分子量: 176.215
• InChiKey: OETGHKDIIIFUBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  3-甲基-4-苯基-二氢-呋喃-2-酮 在 氨 作用下， 生成 4-hydroxy-2-methyl-3-phenyl-butyric acid amide
  参考文献：
  名称：

  α-Methylene-γ-phenyl-γ-butyrolactone

  摘要：

  DOI：

  10.1021/ja01622a081
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 palladium on activated charcoal 、 溶剂黄146 作用下， 生成 3-甲基-4-苯基-二氢-呋喃-2-酮
  参考文献：
  名称：

  α-Methylene-γ-phenyl-γ-butyrolactone

  摘要：

  DOI：

  10.1021/ja01622a081

文献信息

• Distal-Selective Hydroformylation using Scaffolding Catalysis
  作者：Candice L. Joe、Thomas P. Blaisdell、Allison F. Geoghan、Kian L. Tan

  DOI：10.1021/ja504247g

  日期：2014.6.18

  In hydroformylation, phosphorus-based directing groups have been consistently successful at placing the aldehyde on the carbon proximal to the directing group. The design and synthesis of a novel catalytic directing group are reported that promotes aldehyde formation on the carbon distal relative to the directing functionality. This scaffolding ligand, which operates through a reversible covalent bond

  在加氢甲酰化中，基于磷的导向基团一直成功地将醛置于与导向基团相邻的碳上。据报道，一种新型催化导向基团的设计和合成促进了相对于导向功能的碳远端的醛形成。这种支架配体通过与底物的可逆共价键起作用，已应用于高烯丙醇的非对映选择性加氢甲酰化，以选择性地提供 δ-内酯。改变醇和烯烃之间的距离表明，高烯丙醇使远端内酯具有最高水平的区域选择性。
• An asymmetric synthesis of esters and γ-lactones with simultaneous construction of vicinal stereogenic carbons at the α- and β-position starting from optically active 1-chlorovinyl p-tolyl sulfoxides
  作者：Shimpei Sugiyama、Nobuhito Nakaya、Tsuyoshi Satoh

  DOI：10.1016/j.tetasy.2008.01.040

  日期：2008.3

  Treatment of optically active 1-chlorovinyl p-tolyl sulfoxides with two different substituents at the 2-position, which were synthesized from aldehydes or unsymmetrical ketones and (R)-(-)-chloromethyl p-tolyl sulfoxide in two or three steps, with the lithium enolate of carboxylic acid tert-butyl esters gave the adducts with substituents at the alpha- and beta-position with high 1,3- and 1,4-chiral induction from the stereogenic sulfur center in high yields. The adducts were converted to optically active esters and gamma-lactones having stereogenic centers at the alpha- and beta-position in good to high yields. This procedure offers a new method for a synthesis of optically active carboxylic acid derivatives with stereogenic centers at the alpha- and beta-position. (C) 2008 Elsevier Ltd. All rights reserved.
• SYNTHESIS OF PROTOTYPES FOR RENIN INHIBITORS
  申请人：CIBA-GEIGY AG

  公开号：EP0756590A1

  公开（公告）日：1997-02-05
• [EN] SYNTHESIS OF PROTOTYPES FOR RENIN INHIBITORS<br/>[FR] SYNTHESE DES PROTOTYPES DES INHIBITEURS DE LA RENINE
  申请人：CIBA-GEIGY AG

  公开号：WO1995029150A1

  公开（公告）日：1995-11-02

  (EN) Prototype renin inhibitors having general structure (I), where n is 0-3 inclusive, A are either both hydrogen atoms or together are a single carbon-nitrogen bond, R1 is hydrogen, or hydrocarbylcarboxy wherein the hydrocarbyl entity is selected from the group consisting of alkyl of 1 to 6 carbon atoms or aralkyl of 7 to 10 carbon atoms, R2 and R3 or independently alkyl of 1 to 4 carbon atoms, R4 is alkyl of 1 to 6 carbon atoms or a substituent of aliphatic character such as, for example, butyl, 2-morpholinoethyl or 2-carbamoyl-2-methyl-propyl, R5 is selected from aromatics, substitued aromatics and heteroaromatics, substituted or unsubstituted cycloalkyls, cycloalkenes having 3 to 8 carbon atoms, with substituents selected from alkyl, alkoxy of 3 to 10 carbon atoms and alkoxy derivatives such as 3-methoxy-propyloxy, primary and secondary amides, alkyl derivatives, are prepared by novel multistep synthesis. Such compounds are valuable intermediates for the manufacture of pharmaceutical such as Renin inhibitors and HIV-protease inhibitors.(FR) Prototypes d'inhibiteurs de la rénine ayant la structure générale (I) dans laquelle n vaut de 0 à 3 inclus, A représente soit deux atomes d'hydrogène, soit une liaison simple carbone-azote; R1 représente hydrogène ou hydrocarbylcarboxy où l'entité hydrocarbyle est sélectionnée dans le groupe comprenant alkyle de 1 à 6 atomes de carbone ou aralkyle de 7 à 10 atomes de carbone, R2 et R3 représentent, indépendamment, alkyle de 1 à 4 atomes de carbone, R4 représente alkyle de 1 à 6 atomes de carbone ou un substituant de caractère aliphatique tel que, par exemple, butyle, 2-morpholinoéthyle ou 2-carbamoyle-2-méthyle-propyle, R5 est sélectionné parmi des composés aromatiques, des composés aromatiques et hétéroaromatiques substitués, des cycloalkyles substitués ou non substitués, des cycloalcènes possédant de 3 à 8 atomes de carbone, lesdits substituants étant sélectionnés entre alkyle, alcoxy de 3 à 10 atomes de carbone, et des dérivés d'alcoxy, tels que 3-méthoxy-propyloxy, des amides primaires et secondaires et des dérivés d'alkyle. Ces prototypes sont préparés à l'aide d'une nouvelle synthèse à plusieurs étapes. Ces composés sont des produits intermédiaires précieux utilisés dans la fabrication de produits pharmaceutiques, tels que des inhibiteurs de la rénine et des inhibiteurs de la protéase du VIH.
• α-Methylene-γ-phenyl-γ-butyrolactone
  作者：Eugene E. Van Tamelen、Shirley Rosenberg Bach

  DOI：10.1021/ja01622a081

  日期：1955.9