4S4-[3'-(hydroxy)phenyl]-7-methoxy-3,4-dihydrocoumarin | 1240093-50-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: 4S4-[3'-(hydroxy)phenyl]-7-methoxy-3,4-dihydrocoumarin
• 英文别名: 4-(3-Hydroxyphenyl)-7-methoxy-3,4-dihydrochromen-2-one
• CAS: 1240093-50-8
• 化学式: C₁₆H₁₄O₄
• 分子量: 270.285
• InChiKey: YFAMGZMCTLYDDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  胡椒醛 、 4S4-[3'-(hydroxy)phenyl]-7-methoxy-3,4-dihydrocoumarin 在 N,N-二异丙基乙胺 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以81%的产率得到3-[1,3-Benzodioxol-5-yl(hydroxy)methyl]-4-(3-hydroxyphenyl)-7-methoxy-3,4-dihydrochromen-2-one
  参考文献：
  名称：

  A simple and scalable procedure for TiCl4-promoted aldol reaction

  摘要：

  TiCl4-promoted aldol reaction was carried out by adding TiCl4 to a solution of the aldol reaction substrates and (i-Pr)(2)NEt (DIPEA) in CH2Cl2. Compared to the conventional order of addition (sequentially adding TiCl4, DIPEA, and piperonal to the lactone 2 in CH2Cl2), this simplified procedure, gave a much cleaner reaction that could be executed on large scale and without cryogenic cooling. However this procedure provided no stereoselectivity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.06.037
• 作为产物：
  描述：

  4S-4-[3'-(benzyloxy)phenyl]-7-methoxy-3,4-dihydrocoumarin 在 palladium-carbon H2 作用下， 以 水 、 乙酸乙酯 为溶剂， 生成 4S4-[3'-(hydroxy)phenyl]-7-methoxy-3,4-dihydrocoumarin
  参考文献：
  名称：

  Process of making 3-phenyl-1-methylenedioxyphenyl-indane-2-carboxylic

  摘要：

  本发明涉及一种改进的制备芳香环并环戊烷衍生物的方法。本发明制备的首选化合物为茚酸酯和环戊[b]吡啶衍生物。本发明制备的最优化合物为(+)(1S,2R,3S)-3-[2-(2-羟乙基氧基)4-甲氧基苯基]-1-(3,4-亚甲二氧基苯基)-5-(丙-1-氧基)茚-2-羧酸及其药学上可接受的盐和(+)(1S,2R,3S)-3-(2-羧甲氧基-4-甲氧基苯基)-1-(3,4-亚甲二氧基苯基)-5-(丙-1-氧基)茚-2-羧酸及其药学上可接受的盐。此外，本发明还涉及用于制备这些化合物的新型中间体。

  公开号：

  US06114549A1

文献信息

• A simple and scalable procedure for TiCl4-promoted aldol reaction
  作者：Qiaogong Su、Jeffery L. Wood

  DOI：10.1016/j.tetlet.2010.06.037

  日期：2010.8

  TiCl4-promoted aldol reaction was carried out by adding TiCl4 to a solution of the aldol reaction substrates and (i-Pr)(2)NEt (DIPEA) in CH2Cl2. Compared to the conventional order of addition (sequentially adding TiCl4, DIPEA, and piperonal to the lactone 2 in CH2Cl2), this simplified procedure, gave a much cleaner reaction that could be executed on large scale and without cryogenic cooling. However this procedure provided no stereoselectivity. (C) 2010 Elsevier Ltd. All rights reserved.
• Process of making 3-phenyl-1-methylenedioxyphenyl-indane-2-carboxylic
  申请人：SmithKline Beecham Corporation

  公开号：US06114549A1

  公开（公告）日：2000-09-05

  Invented is an improved process for preparing aromatic ring-fused cyclopentane derivatives. Preferred compounds prepared by this invention are indane carboxylates and cyclopentano[b]pyridine derivatives. The most preferred compounds prepared by this invention are (+)(1S, 2R, 3S)-3-[2-(2-hydroxyeth-1-yloxy)4-methoxyphenyl]-1-(3,4-methylenedioxypheny l)-5-(prop-1-yloxy)indane-2-carboxylic acid and pharmaceutically acceptable salts thereof and (+)(1S, 2R, 3S)-3-(2-carboxymethoxy-4-methoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(p rop-1-yloxy)indane-2-carboxylic acid and pharmaceutically acceptable salts thereof. Also invented are novel intermediates useful in preparing these compounds.

  本发明涉及一种改进的制备芳香环并环戊烷衍生物的方法。本发明制备的首选化合物为茚酸酯和环戊[b]吡啶衍生物。本发明制备的最优化合物为(+)(1S,2R,3S)-3-[2-(2-羟乙基氧基)4-甲氧基苯基]-1-(3,4-亚甲二氧基苯基)-5-(丙-1-氧基)茚-2-羧酸及其药学上可接受的盐和(+)(1S,2R,3S)-3-(2-羧甲氧基-4-甲氧基苯基)-1-(3,4-亚甲二氧基苯基)-5-(丙-1-氧基)茚-2-羧酸及其药学上可接受的盐。此外，本发明还涉及用于制备这些化合物的新型中间体。