(3R,5R)-3,5-dimethyl-5-phenyldihydrofuran-2(3H)-one | 950489-50-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3R,5R)-3,5-dimethyl-5-phenyldihydrofuran-2(3H)-one
• 英文别名: (3R,5R)-3,5-dimethyl-5-phenyloxolan-2-one
• CAS: 950489-50-6
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: BQZKDWCIFAWXHY-BXKDBHETSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  (3R,5R)-3,5-dimethyl-5-phenyldihydrofuran-2(3H)-one 在 ruthenium trichloride sodium periodate 、 硼烷 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 四氯化碳 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 20.0h， 生成 (2R,4R)-2,4-dimethyl-5-oxotetrahydrofuran-2-carbaldehyde
  参考文献：
  名称：

  Preparation of enantiopure 3,5,5-trialkyl-γ-butyrolactones by diastereospecific 5-endo halo lactonizations

  摘要：

  A new preparation of 3,5,5-trialkyl-gamma-butyrolactones of defined absolute configuration is reported. This method involves the diastereoselective alkylation of 3,4-ethylenic acids after incorporation of a chiral Evans auxiliary, and then after separation of the two diastereomers and hydrolysis of the auxiliary, stereospecific halo lactonizations. This method was applied to the preparation of a natural product, present in a sponge. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.05.028
• 作为产物：
  描述：

  (R)-3-((R,E)-2-methyl-4-phenylpent-3-enoyl)-4-phenyloxazolidin-2-one 在 lithium hydroxide 、 偶氮二异丁腈 、 双氧水 、 三正丁基氢锡 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 4.0h， 生成 (3R,5R)-3,5-dimethyl-5-phenyldihydrofuran-2(3H)-one
  参考文献：
  名称：

  Preparation of enantiopure 3,5,5-trialkyl-γ-butyrolactones by diastereospecific 5-endo halo lactonizations

  摘要：

  A new preparation of 3,5,5-trialkyl-gamma-butyrolactones of defined absolute configuration is reported. This method involves the diastereoselective alkylation of 3,4-ethylenic acids after incorporation of a chiral Evans auxiliary, and then after separation of the two diastereomers and hydrolysis of the auxiliary, stereospecific halo lactonizations. This method was applied to the preparation of a natural product, present in a sponge. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.05.028

文献信息

• A New Entry to Asymmetric Synthesis of Optically Active α,γ-Substituted γ-Butyrolactones, Using a Carbohydrate Derived Amide as Both a Chiral Auxiliary and a Proton Source
  作者：Ling-Lin Huang、Ming-Hua Xu、Guo-Qiang Lin

  DOI：10.1021/jo0485637

  日期：2005.1.1

  A new entry for the asymmetric synthesis of optically active α,γ-substituted γ-butyrolactones was developed by using a carbohydrate-derived amide as both a chiral auxiliary and a proton source. Unlike the previously reported examples, the chiral auxiliary employed in this reaction also successfully functioned as a protonating agent. Excellent asymmetric induction could be achieved by this dual stereoselective

  通过使用碳水化合物衍生的酰胺作为手性助剂和质子源，为光学活性α，γ-取代的γ-丁内酯的不对称合成开辟了一条新途径。与先前报道的实例不同，在该反应中使用的手性助剂也成功地用作质子化剂。在反应过程中通过这种双重立体选择性控制可以实现出色的不对称诱导。
• Chiral ligand control in enantioselective reduction of ketones by SmI2 for ketyl radical addition to olefins
  作者：Koichi Mikami、Makoto Yamaoka

  DOI：10.1016/s0040-4039(98)00799-0

  日期：1998.6

  Samarium(II) diiodide-mediated reductive coupling of ketones with α,β-unsaturated esters is shown to afford enantioselectively γ-butyrolactones by the addition of 2,2′-bis(diphenylphosphinyl)-1,1′-binaphthyl (BINAPO) as a chiral ligand.

  io（II）的二碘化of介导的酮与α，β-不饱和酯的还原偶联显示通过添加2,2'-双（二苯基膦基）-1,1'-联萘基（BINAPO）提供对映选择性的γ-丁内酯。手性配体。
• Preparation of enantiopure 3,5,5-trialkyl-γ-butyrolactones by diastereospecific 5-endo halo lactonizations
  作者：Jean-Marc Garnier、Sylvie Robin、Régis Guillot、Gérard Rousseau

  DOI：10.1016/j.tetasy.2007.05.028

  日期：2007.7

  A new preparation of 3,5,5-trialkyl-gamma-butyrolactones of defined absolute configuration is reported. This method involves the diastereoselective alkylation of 3,4-ethylenic acids after incorporation of a chiral Evans auxiliary, and then after separation of the two diastereomers and hydrolysis of the auxiliary, stereospecific halo lactonizations. This method was applied to the preparation of a natural product, present in a sponge. (c) 2007 Elsevier Ltd. All rights reserved.