(R)-3-allyl-3-(3,4-dimethoxyphenyl)dihydrofuran-2(3H)-one | 145473-51-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-3-allyl-3-(3,4-dimethoxyphenyl)dihydrofuran-2(3H)-one
• 英文别名: (3R)-3-(3,4-dimethoxyphenyl)-3-prop-2-enyloxolan-2-one
• CAS: 145473-51-4
• 化学式: C₁₅H₁₈O₄
• 分子量: 262.306
• InChiKey: HGXNLIDZWSXCIH-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-3-allyl-3-(3,4-dimethoxyphenyl)dihydrofuran-2(3H)-one 在 二甲基硫 、 臭氧 作用下， 以 四氢呋喃 为溶剂， 生成 (R)-3-((E)-But-2-enyl)-3-(3,4-dimethoxy-phenyl)-dihydro-furan-2-one
  参考文献：
  名称：

  Highly enantioselective creation of quaternary carbons in a halolactonization of bis-γ,δ-unsaturated carboxylic imides derived from a camphorsultam: Enantioselective synthesis of (+)-mesembrine

  摘要：

  Iodolactonization of symmetrical diene-carboxylic imides (3a,b), derived from a camphorsultam, afforded chiral lactones (5) and (6) possessing aromatic substituents on quaternary carbons in high enantioselectivity with moderate diastereoselectivity.

  DOI：

  10.1016/s0040-4039(00)60916-4
• 作为产物：
  描述：

  2-(3,4-dimethoxyphenyl)-1-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decan-4-yl]-2-prop-2-enylpent-4-en-1-one 在 氢氧化钾 、 iodonium(di-γ-collidine) perchlorate 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 48.0h， 生成 (R)-3-allyl-3-(3,4-dimethoxyphenyl)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  Highly enantioselective creation of quaternary carbons in a halolactonization of bis-γ,δ-unsaturated carboxylic imides derived from a camphorsultam: Enantioselective synthesis of (+)-mesembrine

  摘要：

  Iodolactonization of symmetrical diene-carboxylic imides (3a,b), derived from a camphorsultam, afforded chiral lactones (5) and (6) possessing aromatic substituents on quaternary carbons in high enantioselectivity with moderate diastereoselectivity.

  DOI：

  10.1016/s0040-4039(00)60916-4

文献信息

• A Palladium-Catalyzed Asymmetric Allylic Alkylation Approach to α-Quaternary γ-Butyrolactones
  作者：Marllon Nascimento de Oliveira、Jeremy Fournier、Stellios Arseniyadis、Janine Cossy

  DOI：10.1021/acs.orglett.6b02971

  日期：2017.1.6

  The Pd-catalyzed asymmetric allylic alkylation (Pd-AAA) of enol carbonates derived from γ-butyrolactones is reported, affording the corresponding enantioenriched α,α′-disubstituted γ-butyrolactones in both high yields and high enantioselectivities (up to 94% ee). This method was eventually applied to the synthesis of chiral spirocyclic compounds.

  据报道，由γ-丁内酯衍生的烯醇碳酸酯的Pd催化不对称烯丙基烷基化（Pd-AAA），可提供高产率和高对映选择性（高达94％ee）的相应的对映体富集的α，α'-二取代γ-丁内酯。 。该方法最终应用于手性螺环化合物的合成。
• Highly enantioselective creation of quaternary carbons in a halolactonization of bis-γ,δ-unsaturated carboxylic imides derived from a camphorsultam: Enantioselective synthesis of (+)-mesembrine
  作者：Tsutomu Yokomatsu、Haruo Iwasawa、Shiroshi Shibuya

  DOI：10.1016/s0040-4039(00)60916-4

  日期：1992.11

  Iodolactonization of symmetrical diene-carboxylic imides (3a,b), derived from a camphorsultam, afforded chiral lactones (5) and (6) possessing aromatic substituents on quaternary carbons in high enantioselectivity with moderate diastereoselectivity.