7-hydroxy-5-methoxy-4-propyl-8-tigloylcoumarin | 334881-59-3

• 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-4-propyl-8-tigloylcoumarin
• 英文别名: 7-hydroxy-5-methoxy-8-[(E)-2-methylbut-2-enoyl]-4-propylchromen-2-one
• CAS: 334881-59-3
• 化学式: C₁₈H₂₀O₅
• 分子量: 316.354
• InChiKey: CUNMEXGLJIXOHA-UXBLZVDNSA-N

物化性质

• 熔点：
  122-124 °C
• 沸点：
  525.9±50.0 °C(Predicted)
• 密度：
  1.188±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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-4-propyl-8-tigloylcoumarin 在 奎宁 作用下， 以 氯苯 为溶剂， 反应 21.0h， 生成 (8R,9S)-8,9-dihydro-8,9-dimethyl-5-methoxy-4-propyl-2H,10H-benzo[1,2-b;5,6-b']dipyran-2,10-dione
  参考文献：
  名称：

  Solvent effects on stereoselectivity in 2,3-dimethyl-4-chromanone cyclization by quinine-catalyzed asymmetric intramolecular oxo-Michael addition

  摘要：

  Examination of the quinine-catalyzed asymmetric intramolecular oxo-Michael addition of o-tigloylphenol in various solvents led to high stereoselectivity in chromanone cyclization when chlorobenzene was used as a solvent, giving cis-2,3-dimethyl-4-chromanone with 60% de and 98% ee. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00461-4
• 作为产物：
  描述：

  5,7-二甲氧基-4-丙基-2H-苯并吡喃-2-酮 在 四氯化锡 、 magnesium iodide 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 168.0h， 生成 7-hydroxy-5-methoxy-4-propyl-8-tigloylcoumarin
  参考文献：
  名称：

  Solvent effects on stereoselectivity in 2,3-dimethyl-4-chromanone cyclization by quinine-catalyzed asymmetric intramolecular oxo-Michael addition

  摘要：

  Examination of the quinine-catalyzed asymmetric intramolecular oxo-Michael addition of o-tigloylphenol in various solvents led to high stereoselectivity in chromanone cyclization when chlorobenzene was used as a solvent, giving cis-2,3-dimethyl-4-chromanone with 60% de and 98% ee. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00461-4

文献信息

• Sekino, Etsuko; Kumamoto, Takuya; Tanaka, Tomohiro, Journal of Organic Chemistry, 2004, vol. 69, # 8, p. 2760 - 2767
  作者：Sekino, Etsuko、Kumamoto, Takuya、Tanaka, Tomohiro、Ikeda, Tomoko、Ishikawa, Tsutomu

  DOI：——

  日期：——
• Solvent effects on stereoselectivity in 2,3-dimethyl-4-chromanone cyclization by quinine-catalyzed asymmetric intramolecular oxo-Michael addition
  作者：Tomohiro Tanaka、Takuya Kumamoto、Tsutomu Ishikawa

  DOI：10.1016/s0957-4166(00)00461-4

  日期：2000.12

  Examination of the quinine-catalyzed asymmetric intramolecular oxo-Michael addition of o-tigloylphenol in various solvents led to high stereoselectivity in chromanone cyclization when chlorobenzene was used as a solvent, giving cis-2,3-dimethyl-4-chromanone with 60% de and 98% ee. (C) 2001 Elsevier Science Ltd. All rights reserved.