5,7-Dimethoxy-8-((E)-2-methyl-but-2-enoyl)-chromen-2-one | 181628-96-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 5,7-Dimethoxy-8-((E)-2-methyl-but-2-enoyl)-chromen-2-one
• 英文别名: 5,7-dimethoxy-8-[(E)-2-methylbut-2-enoyl]chromen-2-one
• CAS: 181628-96-6
• 化学式: C₁₆H₁₆O₅
• 分子量: 288.3
• InChiKey: KSCJGFDNGWOGGA-WEVVVXLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,7-Dimethoxy-8-((E)-2-methyl-but-2-enoyl)-chromen-2-one 在 TEA 、 三氯化硼 、 lithium tri-t-butoxyaluminum hydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 丙酮 为溶剂， 反应 30.67h， 生成 (8S,9R,10R)-10-Hydroxy-5-methoxy-8,9-dimethyl-9,10-dihydro-8H-pyrano[2,3-f]chromen-2-one
  参考文献：
  名称：

  Diastereoselective preparation of a trans, trans 2, 3-dimethylchroman-4-ol skeleton: A model synthetic approach to anti-HIV-1 active Calophyllum coumarins

  摘要：

  A model synthetic study of anti-HIV-1 active Calophyllum coumarins using 5, 7-dimethoxycoumarin (limettin) is described. Successive reactions of the CsF-induced intramolecular Michael type addition of an o-tigloylphenol followed by reduction with lithium tri-tert-butoxyaluminum hydride led to easy and diastereoselective access to a trans, trans 2, 3-dimethylchroman-4-ol ring, which is suggested to be the most responsible skeleton for the activity. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)10004-7
• 作为产物：
  描述：

  (E)-2-甲基-2-丁烯酰氯 、 5,7-二甲氧基香豆素 在 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以48%的产率得到5,7-Dimethoxy-8-((E)-2-methyl-but-2-enoyl)-chromen-2-one
  参考文献：
  名称：

  Diastereoselective preparation of a trans, trans 2, 3-dimethylchroman-4-ol skeleton: A model synthetic approach to anti-HIV-1 active Calophyllum coumarins

  摘要：

  A model synthetic study of anti-HIV-1 active Calophyllum coumarins using 5, 7-dimethoxycoumarin (limettin) is described. Successive reactions of the CsF-induced intramolecular Michael type addition of an o-tigloylphenol followed by reduction with lithium tri-tert-butoxyaluminum hydride led to easy and diastereoselective access to a trans, trans 2, 3-dimethylchroman-4-ol ring, which is suggested to be the most responsible skeleton for the activity. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)10004-7

文献信息

• Cesium Fluoride-Induced Intramolecular Michael Addition:  Highly Diastereoselective Ring Construction of a <i>trans</i>-2,3-Dimethylchroman-4-one
  作者：Tsutomu Ishikawa、Yumie Oku、Ken-Ichiro Kotake、Hisashi Ishii

  DOI：10.1021/jo961170q

  日期：1996.1.1
• Diastereoselective preparation of a trans, trans 2, 3-dimethylchroman-4-ol skeleton: A model synthetic approach to anti-HIV-1 active Calophyllum coumarins
  作者：Tsutomu Ishikawa、Yumie Oku、Ken-Ichiro Kotake

  DOI：10.1016/s0040-4020(97)10004-7

  日期：1997.11

  A model synthetic study of anti-HIV-1 active Calophyllum coumarins using 5, 7-dimethoxycoumarin (limettin) is described. Successive reactions of the CsF-induced intramolecular Michael type addition of an o-tigloylphenol followed by reduction with lithium tri-tert-butoxyaluminum hydride led to easy and diastereoselective access to a trans, trans 2, 3-dimethylchroman-4-ol ring, which is suggested to be the most responsible skeleton for the activity. (C) 1997 Elsevier Science Ltd.