2-(3,4-dimethoxyphenyl)-7-methoxy-3-methyl-5-[(E)-prop-1-enyl]-2,3-dihydrobenzo[b]furan

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: 2-(3,4-dimethoxyphenyl)-7-methoxy-3-methyl-5-[(E)-prop-1-enyl]-2,3-dihydrobenzo[b]furan
• 英文别名: (2R,3S)-2,3-dihydro-2-(3,4-dimethoxyphenyl)-3-methyl-5-(E)-propenylbenzofuran；(2R,3S)-2-(3,4-dimethoxyphenyl)-7-methoxy-3-methyl-5-[(E)-prop-1-enyl]-2,3-dihydro-1-benzofuran
• 化学式: C₂₁H₂₄O₄
• 分子量: 340.419
• InChiKey: ITFKWUHXYCXXFF-RVZKHINXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(3,4-dimethoxyphenyl)-7-methoxy-3-methyl-5-[(E)-prop-1-enyl]-2,3-dihydrobenzo[b]furan 在 camphor-10-sulfonic acid 、 sodium hydroxide 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以95%的产率得到(2S,3S)-2-(3,4-二甲氧苯基)-7-甲氧基-3-甲基-5-[(1E)-丙-1-烯-1-基]-2,3-二氢-1-苯并呋喃
  参考文献：
  名称：

  Rh(II)-catalyzed enantioselective synthesis of acuminatin through a C–H insertion reaction of a non-stabilized carbenoid

  摘要：

  An efficient and practical asymmetric synthesis of the 2,3-dihydrobenzo[b]furan neolignan acuminatin was achieved by using trans-isoeugenol as the starting material. The key step is an intramolecular C-H insertion through a non-stabilized carbenoid, prepared by decomposition of a tosylhydrazone in the presence of an anthracenyl-derived cinchonidine quaternary ammonium salt as a chiral phase-transfer catalyst. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.04.086
• 作为产物：
  描述：

  (E)-2-甲氧基-4-(1-丙烯基苯酚) 在 吡啶 、 四甲基乙二胺 、 双(三甲基硅烷基)氨基钾 、 potassium carbonate 、 戴斯-马丁氧化剂 、 magnesium 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 62.0h， 生成 2-(3,4-dimethoxyphenyl)-7-methoxy-3-methyl-5-[(E)-prop-1-enyl]-2,3-dihydrobenzo[b]furan
  参考文献：
  名称：

  Rh(II)-catalyzed enantioselective synthesis of acuminatin through a C–H insertion reaction of a non-stabilized carbenoid

  摘要：

  An efficient and practical asymmetric synthesis of the 2,3-dihydrobenzo[b]furan neolignan acuminatin was achieved by using trans-isoeugenol as the starting material. The key step is an intramolecular C-H insertion through a non-stabilized carbenoid, prepared by decomposition of a tosylhydrazone in the presence of an anthracenyl-derived cinchonidine quaternary ammonium salt as a chiral phase-transfer catalyst. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.04.086

文献信息

• Rh(II)-catalyzed enantioselective synthesis of acuminatin through a C–H insertion reaction of a non-stabilized carbenoid
  作者：Cristóbal López-Sánchez、Míriam Álvarez-Corral、Leticia Jiménez-González、Manuel Muñoz-Dorado、Ignacio Rodríguez-García

  DOI：10.1016/j.tet.2013.04.086

  日期：2013.7

  An efficient and practical asymmetric synthesis of the 2,3-dihydrobenzo[b]furan neolignan acuminatin was achieved by using trans-isoeugenol as the starting material. The key step is an intramolecular C-H insertion through a non-stabilized carbenoid, prepared by decomposition of a tosylhydrazone in the presence of an anthracenyl-derived cinchonidine quaternary ammonium salt as a chiral phase-transfer catalyst. (C) 2013 Elsevier Ltd. All rights reserved.