(-)-(S)-5-methyl-5-phenylfuran-2(5H)-one | 52264-92-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: (-)-(S)-5-methyl-5-phenylfuran-2(5H)-one
• 英文别名: (S)-5-methyl-5-phenylfuran-2(5H)-one；(5S)-5-Methyl-5-phenylfuran-2(5H)-one；(5S)-5-methyl-5-phenylfuran-2-one
• CAS: 52264-92-3；53774-21-3；67596-41-2；67545-38-4
• 化学式: C₁₁H₁₀O₂
• 分子量: 174.199
• InChiKey: JNYXOXHKFXEQMJ-NSHDSACASA-N

物化性质

• 沸点：
  328.4±31.0 °C(Predicted)
• 密度：
  1.144±0.06 g/cm3(Predicted)

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：
  0.18
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-phenyl-3,4-pentdien-2-ol 在 吡啶 、 Ag⁽¹⁺⁾*C₄₄H₂₈O₄P^(1-) 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 24.5h， 生成 (-)-(S)-5-methyl-5-phenylfuran-2(5H)-one
  参考文献：
  名称：

  Chiral Silver Phosphate-Catalyzed Cycloisomeric Kinetic Resolution of α-Allenic Alcohols

  摘要：

  A kinetic resolution of a-allenic alcohols is realized through chiral silver phosphate-catalyzed cycloisomerization with high stereoselectivity (selectivity factor up to 189) and tolerance of a variety of functional groups. A mechanistic model is proposed to interpret the origin of the high stereoselectivity and broad substrate scope.

  DOI：

  10.1021/ja300453u

文献信息

• Palladium-catalyzed asymmetric intermolecular Mizoroki–Heck reaction for construction of a chiral quaternary carbon center
  作者：Qing-Song Zhang、Shi-Li Wan、Di Chen、Chang-Hua Ding、Xue-Long Hou

  DOI：10.1039/c5cc03601a

  日期：——

  A palladium-catalyzed asymmetric intermolecular Mizoroki-Heck reaction for the construction of chiral quaternary carbon center is developed, affording 2,2-disubstituted 2,5-dihydrofurans in high yield with excellent enantioselectivity. The products are easily converted...

  开发了钯催化的不对称分子间米佐罗基-赫克反应，用于手性季碳中心的构建，可提供高产率的2,2-二取代的2,5-二氢呋喃，具有出色的对映选择性。产品易于转换...
• Synthesis of chiral butenolides using amino-thiocarbamate-catalyzed asymmetric bromolactonization
  作者：Chong Kiat Tan、Jun Cheng Er、Ying-Yeung Yeung

  DOI：10.1016/j.tetlet.2014.01.009

  日期：2014.2

  The asymmetric cyclization of 4,4-disubstituted 3-butenoic acids is studied. Amino-thiocarbamates are used as the catalysts and N-bromosuccinimide is used as the stoichiometric halogen source. The resulting gamma-butanolide products are readily converted into the corresponding gamma-butenolides (up to 58% ee) derivatives in one-pot. (C) 2014 Elsevier Ltd. All rights reserved.
• Albinati, Alberto; Bravo, Pierfrancesco; Ganazzoli, Fabio, Journal of the Chemical Society. Perkin transactions I, 1986, p. 1405 - 1416
  作者：Albinati, Alberto、Bravo, Pierfrancesco、Ganazzoli, Fabio、Resnati, Giuseppe、Viani, Fiorenza

  DOI：——

  日期：——
• Enantiodivergent syntheses of γ-substituted butenolides with tertiary and quaternary asymmetric centers
  作者：Katsufumi Suzuki、Kohei Inomata

  DOI：10.1016/s0040-4039(02)02711-9

  日期：2003.1

  Continuous nucleophilic addition with several organometallic reagents to tricyclic lactone (-)-1 proceeded diastereoselectively. Newly generated tertiary and quaternary asymmetric centers were controlled by the order in which the nucleophilic reagents were added. Using this methodology, enantiodivergent syntheses of several gamma-substituted butenolides with tertiary and quaternary asymmetric centers were established from a single chiral material. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Chiral Silver Phosphate-Catalyzed Cycloisomeric Kinetic Resolution of α-Allenic Alcohols
  作者：Yan Wang、Kuan Zheng、Ran Hong

  DOI：10.1021/ja300453u

  日期：2012.3.7

  A kinetic resolution of a-allenic alcohols is realized through chiral silver phosphate-catalyzed cycloisomerization with high stereoselectivity (selectivity factor up to 189) and tolerance of a variety of functional groups. A mechanistic model is proposed to interpret the origin of the high stereoselectivity and broad substrate scope.