5-methyl-5-(naphthalen-2-yl)dihydrofuran-2(3H)-one | 21053-55-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-methyl-5-(naphthalen-2-yl)dihydrofuran-2(3H)-one
• 英文别名: 5-Methyl-5-naphthalen-2-yloxolan-2-one
• CAS: 21053-55-4
• 化学式: C₁₅H₁₄O₂
• 分子量: 226.275
• InChiKey: RPEAXJCKWAGUGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 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-methyl-5-(naphthalen-2-yl)dihydrofuran-2(3H)-one 在 Pd-BaSO₄ 甲烷磺酸 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 90.0 ℃ 、344.74 kPa 条件下， 反应 10.0h， 生成 1-methyl-1,2,3,4-tetrahydro-4-phenanthrone
  参考文献：
  名称：

  Conformational effects on the enantioselective recognition of 4-(3,5-dinitrobenzamido)-1,2,3,4-tetrahydrophenanthrene derivatives by a Naproxen-derived chiral stationary phase

  摘要：

  4-(3,5-Dinitrobenzamido)-1,2,3,4-tetrahydrophenanthrene and derivatives having methyl groups in various positions on the tetrahydro ring were synthesized and resolved on an (S)-Naproxen-derived chiral stationary phase. The difference in the Gibbs free energy, DeltaDeltaG, of the transient diastereomeric adsorbates was determined from the chromatographic data. The highest enantioselectivity was observed for cis-4-(3,5-dinitrobenzamido)-3-methyl-1,2,3,4-tetrahydrophenanthrene. Introducing methyl groups into other positions of the tetrahydrophenanthrene ring proved to be detrimental to enantioselectivity. Prior studies indicate that, in the 4-(3,5-dinitrobenzamido)1,2,3,4-tetrahydrophenanthrene used in the Whelk-O chiral HPLC columns, the 3,5-dinitrobenzamide group occupies a pseudoaxial position, thus forming one wall of a binding cleft owing to its spatial relationship with the naphthyl portion of the selector. The effect of the methyl substituents on enantioselectivity is attributed to their ability to both influence the 'psuedoaxiality' of the dinitrobenzamido group and to their ability to sterically hinder the presentation of the 'back face' of this group to the Naproxen-derived selector. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00307-1
• 作为产物：
  描述：

  (E)-4-(naphthalen-2-yl)pent-3-enoic acid 在 硫酸 作用下， 生成 5-methyl-5-(naphthalen-2-yl)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  72.合成与甾醇有关的物质的实验。第XXIX部

  摘要：

  DOI：

  10.1039/jr9410000376

文献信息

• 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。
• ZnI₂/Zn(OTf)₂-TsOH: a versatile combined-acid system for catalytic intramolecular hydrofunctionalization and polyene cyclization
  作者：Ting-Hung Chou、Bo-Hung Yu、Rong-Jie Chein

  DOI：10.1039/c9cc07242j

  日期：——

  combined-acid system using a zinc(II) salt [ZnI2 or Zn(OTf)2] and p-toluene sulfonic acid (TsOH) was investigated for catalytic cationic cyclizations, including intramolecular hydrocarboxylation, hydroalkoxylation, hydroamination, hydroamidation, hydroarylation and polyene cyclizations. This reaction provides easy access to five- and six-membered O- and N-containing saturated heterocyclic compounds, tetrahydronaphthalene

  研究了使用锌（II）盐[ZnI 2或Zn（OTf）2 ]和对甲苯磺酸（TsOH）的温和高效的联合酸体系，用于催化阳离子环化，包括分子内加氢羧基化，加氢烷氧基化，加氢胺化，加氢酰胺化，氢芳基化和多烯环化。该反应可轻松获得五元和六元含O和N的饱和杂环化合物，四氢萘衍生物和多环骨架，并具有良好的马尔可夫尼可夫选择性，并且在温和条件下的收率很高。操作简便，广泛适用性以及使用廉价的市售催化剂使该方案优于现有方法。
• Johnson; Johnson; Petersen, Journal of the American Chemical Society, 1945, vol. 67, p. 1360,1364
  作者：Johnson、Johnson、Petersen

  DOI：——

  日期：——
• 72. Experiments on the synthesis of substances related to the sterols. Part XXIX
  作者：Robert Robinson、S. N. Slater

  DOI：10.1039/jr9410000376

  日期：——
• Conformational effects on the enantioselective recognition of 4-(3,5-dinitrobenzamido)-1,2,3,4-tetrahydrophenanthrene derivatives by a Naproxen-derived chiral stationary phase
  作者：Christian Wolf、William H Pirkle

  DOI：10.1016/s0040-4020(02)00307-1

  日期：2002.4

  4-(3,5-Dinitrobenzamido)-1,2,3,4-tetrahydrophenanthrene and derivatives having methyl groups in various positions on the tetrahydro ring were synthesized and resolved on an (S)-Naproxen-derived chiral stationary phase. The difference in the Gibbs free energy, DeltaDeltaG, of the transient diastereomeric adsorbates was determined from the chromatographic data. The highest enantioselectivity was observed for cis-4-(3,5-dinitrobenzamido)-3-methyl-1,2,3,4-tetrahydrophenanthrene. Introducing methyl groups into other positions of the tetrahydrophenanthrene ring proved to be detrimental to enantioselectivity. Prior studies indicate that, in the 4-(3,5-dinitrobenzamido)1,2,3,4-tetrahydrophenanthrene used in the Whelk-O chiral HPLC columns, the 3,5-dinitrobenzamide group occupies a pseudoaxial position, thus forming one wall of a binding cleft owing to its spatial relationship with the naphthyl portion of the selector. The effect of the methyl substituents on enantioselectivity is attributed to their ability to both influence the 'psuedoaxiality' of the dinitrobenzamido group and to their ability to sterically hinder the presentation of the 'back face' of this group to the Naproxen-derived selector. (C) 2002 Elsevier Science Ltd. All rights reserved.