3-(3',4'-methylenedioxy-5'-methoxy-phenyl)-2-propenoyl chloride | 194660-25-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3-(3',4'-methylenedioxy-5'-methoxy-phenyl)-2-propenoyl chloride
• 英文别名: 3-(7-Methoxy-1,3-benzodioxol-5-yl)prop-2-enoyl chloride
• CAS: 194660-25-8
• 化学式: C₁₁H₉ClO₄
• 分子量: 240.643
• InChiKey: DCUYRZFGFLYCGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  3-(3',4'-methylenedioxy-5'-methoxy-phenyl)-2-propenoyl chloride 在 正丁基锂 、 copper(I) bromide dimethylsulfide complex 作用下， 以 四氢呋喃 为溶剂， 反应 7.5h， 生成 (3(3R),4R)-4-(diphenylmethyl)-3-[3-(3,3-(phenyl)-(3",4"-methylenedioxy-5"-methoxyphenyl))-propanoyl]-2-oxazolidinone
  参考文献：
  名称：

  Enantioselective synthesis of peperomins A, C, D, and analogs — Examination of diastereoselective cuprate conjugate additions to <i>N</i>-enoyl-4-diphenylmethyl-2-oxazolidinones

  摘要：

  A concise and general route to secolignans has been developed. The first total synthesis of secolignans peperomin A (1a), peperomin C (1b), and peperomin D (1c) was accomplished in similar to 28% overall yield over five synthetic steps. Peperomin analogs (1d) and (1e), possessing two differentially substituted aryl groups, were synthesized by a highly selective conjugate addition. The overall yield for the analogs 1d and 1e were 27 and 26%, respectively.

  DOI：

  10.1139/cjc-79-11-1546
• 作为产物：
  描述：

  Ethyl 3-(7-methoxy-1,3-benzodioxol-5-yl)prop-2-enoate 在 sodium hydroxide 、 草酰氯 作用下， 反应 3.33h， 生成 3-(3',4'-methylenedioxy-5'-methoxy-phenyl)-2-propenoyl chloride
  参考文献：
  名称：

  Enantioselective synthesis of peperomins A, C, D, and analogs — Examination of diastereoselective cuprate conjugate additions to <i>N</i>-enoyl-4-diphenylmethyl-2-oxazolidinones

  摘要：

  A concise and general route to secolignans has been developed. The first total synthesis of secolignans peperomin A (1a), peperomin C (1b), and peperomin D (1c) was accomplished in similar to 28% overall yield over five synthetic steps. Peperomin analogs (1d) and (1e), possessing two differentially substituted aryl groups, were synthesized by a highly selective conjugate addition. The overall yield for the analogs 1d and 1e were 27 and 26%, respectively.

  DOI：

  10.1139/cjc-79-11-1546