(3-Formyl-6,8-dimethoxynaphthalen-1-yl) acetate | 155816-95-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (3-Formyl-6,8-dimethoxynaphthalen-1-yl) acetate
• CAS: 155816-95-8
• 化学式: C₁₅H₁₄O₅
• 分子量: 274.273
• InChiKey: JKAZKJGTQTVUQO-UHFFFAOYSA-N

物化性质

• 熔点：
  144-146 °C
• 沸点：
  453.7±45.0 °C(predicted)
• 密度：
  1.241±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  (3-Formyl-6,8-dimethoxynaphthalen-1-yl) acetate 在 N-甲基吗啉 、 chromium dichloride 、 potassium fluoride 、 lithium aluminium tetrahydride 、 18-冠醚-6 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 3-(2-Hydroxypropyl)-6,8-dimethoxynaphthalen-1-ol
  参考文献：
  名称：

  Optically Active Total Synthesis of Calphostin D

  摘要：

  An optically active total synthesis of calphostin D (1a):through dimerization of the chiral o-naphthoquinone 6 has been accomplished. The mechanism of the dimerization has been shown to be an acid-catalyzed process;

  DOI：

  10.1021/jo00087a006
• 作为产物：
  描述：

  4-羟基-5,7-二甲氧基-2-萘羧酸乙酯 在 吡啶 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 19.0h， 生成 (3-Formyl-6,8-dimethoxynaphthalen-1-yl) acetate
  参考文献：
  名称：

  Total Synthesis and Structural Confirmation of the Antimalarial Naphthopyrone Lasionectrin

  摘要：

  The total synthesis of lasionectrin, a naphthopyrone metabolite of an Acremonium-like fungus collected in Equatorial Guinea, is reported. Divergent access to four stereoisomers confirmed the natural product to be the enantiomer of the originally proposed structure. Highlights of the synthesis include ring opening of a chiral oxetane using a thiol, a highly E-selective Julia-Kocienski olefination, and a modified Sharpless/Upjohn dihydroxylation. Palladium-catalyzed carbonylative lactonization was used to assemble the fused naphthopyrone ring system.

  DOI：

  10.1021/acs.orglett.5b03202

文献信息

• Total Synthesis and Structural Confirmation of the Antimalarial Naphthopyrone Lasionectrin
  作者：Vincent L. Poral、Daniel P. Furkert、Margaret A. Brimble

  DOI：10.1021/acs.orglett.5b03202

  日期：2015.12.18

  The total synthesis of lasionectrin, a naphthopyrone metabolite of an Acremonium-like fungus collected in Equatorial Guinea, is reported. Divergent access to four stereoisomers confirmed the natural product to be the enantiomer of the originally proposed structure. Highlights of the synthesis include ring opening of a chiral oxetane using a thiol, a highly E-selective Julia-Kocienski olefination, and a modified Sharpless/Upjohn dihydroxylation. Palladium-catalyzed carbonylative lactonization was used to assemble the fused naphthopyrone ring system.
• Optically Active Total Synthesis of Calphostin D
  作者：Frank M. Hauser、Dipanjan Sengupta、Stephen A. Corlett

  DOI：10.1021/jo00087a006

  日期：1994.4

  An optically active total synthesis of calphostin D (1a):through dimerization of the chiral o-naphthoquinone 6 has been accomplished. The mechanism of the dimerization has been shown to be an acid-catalyzed process;