(R)-5-(4-methoxyphenyl)-5-methylfuran-2(5H)-one | 1548513-42-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (R)-5-(4-methoxyphenyl)-5-methylfuran-2(5H)-one
• 英文别名: 5-(4-methoxyphenyl)-5-methylfuran-2(5H)-one；(5R)-5-(4-methoxyphenyl)-5-methylfuran-2-one
• CAS: 1548513-42-3
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: SXOQCHJYVWWEME-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(4-甲氧基苯基)丙醛 在 N-溴代丁二酰亚胺(NBS) 、 O-[(S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethyl] N-phenylcarbamothioate 、 三乙胺 作用下， 以 正己烷 、 氯仿 为溶剂， 反应 36.08h， 生成 (R)-5-(4-methoxyphenyl)-5-methylfuran-2(5H)-one
  参考文献：
  名称：

  Synthesis of chiral butenolides using amino-thiocarbamate-catalyzed asymmetric bromolactonization

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2014.01.009

文献信息

• Palladium‐Catalyzed Enantioselective γ‐Arylation of β,γ‐Unsaturated Butenolides
  作者：Sanliang Li、Qiaoyu Chen、Junfeng Yang、Junliang Zhang

  DOI：10.1002/anie.202202046

  日期：2022.6.7

  A Pd-catalyzed enantioselective γ-selective arylation of β, γ-unsaturated butenolides is reported. The P-chiral phosphine ligand-AntPhos is essential for the observed high γ-selectivity, excellent enantioselectivity and good yields.

  报道了 Pd 催化的 β，γ-不饱和丁烯内酯的对映选择性 γ-选择性芳基化。P-手性膦配体-AntPhos 对于观察到的高 γ-选择性、优异的对映选择性和良好的产率至关重要。
• Asymmetric Oxidative Lactonization of Enynyl Boronates
  作者：Kezhuo Zhang、Chenchen Li、Yining Jia、Wanxiang Zhao

  DOI：10.1002/anie.202209004

  日期：2022.10.10

  We present herein the first oxidation of enynyl boronates for the synthesis of γ-lactones, including spiro-, and fused-butanolides as well as butenolides that are prevalent in nature products and bioactive molecules. The asymmetric version of this oxidation was also achieved in the presence of chiral ketone and Oxone. This process successively involves the oxidation of C(sp)−B bond, the epoxidation

  我们在此提出了用于合成γ-内酯的烯基硼酸酯的第一次氧化，包括螺环和稠合丁内酯以及在天然产物和生物活性分子中普遍存在的丁烯内酯。这种氧化的不对称形式也在手性酮和 Oxone 的存在下实现。该过程依次涉及 C(sp)-B 键的氧化、C-C 双键的环氧化和内酯化。
• 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.