7-hydroxy-5-methoxy-8-tigloylcoumarin | 181628-99-9

• 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: 7-hydroxy-5-methoxy-8-tigloylcoumarin
• 英文别名: 7-hydroxy-5-methoxy-8-[(E)-2-methylbut-2-enoyl]chromen-2-one
• CAS: 181628-99-9
• 化学式: C₁₅H₁₄O₅
• 分子量: 274.273
• InChiKey: KLPDOESDOHTHQM-XBXARRHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-hydroxy-5-methoxy-8-tigloylcoumarin 在 TEA 作用下， 以 氯仿 、 丙酮 为溶剂， 反应 24.67h， 生成 (8S,9R)-5-Methoxy-8,9-dimethyl-8,9-dihydro-pyrano[2,3-f]chromene-2,10-dione
  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：

  5,7-二甲氧基香豆素 在 三氯化硼 、 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 76.0h， 生成 7-hydroxy-5-methoxy-8-tigloylcoumarin
  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

• An approach to anti-HIV-1 active Calophyllum coumarin synthesis: An enantioselective construction of 2,3-dimethyl-4-chromanone ring by quinine-assisted intramolecular Michael-type addition
  作者：Tsutomu Ishikawa、Yumie Oku、Tomohiro Tanaka、Takuya Kumamoto

  DOI：10.1016/s0040-4039(99)00607-3

  日期：1999.5

  (-)-Quinine effectively catalyzes an intramolecular Michael-type addition of 7-hydroxy-8-tigloylcoumarin to give a diastereoisomeric mixture of the corresponding cyclized coumarin with a 2,3-dimethyl-4-chromanone skeleton. Satisfactory enantioselectivity was observed in a cis-chromanone construction, but not in a trans-one. (C) 1999 Elsevier Science Ltd. All rights reserved.

  (-)-奎宁能够有效地催化7-羟基-8-乙酰基香豆素的分子内迈克尔型加成反应，生成具有2,3-二甲基-4-香豆烷酮骨架的对应环状香豆素的对映异构混合物。在顺式香豆烷酮的构建中观察到了令人满意的对映选择性，但在反式结构中并未观察到对映选择性。（C）1999 Elsevier Science Ltd. 版权所有。
• 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