5,10-Dimethoxy-1H-naphtho[2,3-c]pyran | 253863-56-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 5,10-Dimethoxy-1H-naphtho[2,3-c]pyran
• 英文别名: 5,10-dimethoxy-1H-benzo[g]isochromene
• CAS: 253863-56-8
• 化学式: C₁₅H₁₄O₃
• 分子量: 242.274
• InChiKey: NSUFPSDQMZBKNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,10-Dimethoxy-1H-naphtho[2,3-c]pyran 在 ammonium cerium(IV) nitrate 、 对甲苯磺酸 作用下， 以 水 、 乙腈 、 苯 为溶剂， 反应 3.83h， 生成 pentalongin
  参考文献：
  名称：

  Synthesis of pyranonaphthoquinone antibiotics involving the ring closing metathesis of a vinyl ether

  摘要：

  The synthesis of two antibiotic pyranonaphthoquinones was performed by a straightforward synthetic route utilizing ring closing metathesis. Vinylation of 3-(1-propenyl)-2-hydroxymethyl-1.4-dimethoxynapthalene under iridium catalysis and subsequent ring closing metathesis of 3-(1-propenyl)-2-vinyloxymethyl-1.4-dimethoxynaphthalene with Grubbs' catalyst paved the way to the natural antibiotics pentalongin and psychorubrin. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.03.008
• 作为产物：
  描述：

  trans-2-(hydroxymethyl)-1,4-dimethoxy-3-(1-propenyl)naphthalene 在 Grubbs catalyst first generation 、 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 sodium carbonate 作用下， 以 甲苯 为溶剂， 反应 36.0h， 生成 5,10-Dimethoxy-1H-naphtho[2,3-c]pyran
  参考文献：
  名称：

  Synthesis of pyranonaphthoquinone antibiotics involving the ring closing metathesis of a vinyl ether

  摘要：

  The synthesis of two antibiotic pyranonaphthoquinones was performed by a straightforward synthetic route utilizing ring closing metathesis. Vinylation of 3-(1-propenyl)-2-hydroxymethyl-1.4-dimethoxynapthalene under iridium catalysis and subsequent ring closing metathesis of 3-(1-propenyl)-2-vinyloxymethyl-1.4-dimethoxynaphthalene with Grubbs' catalyst paved the way to the natural antibiotics pentalongin and psychorubrin. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.03.008

文献信息

• Synthesis of Two Naphthoquinone Antibiotics Pentalongin and Psychorubrin
  作者：Bart Kesteleyn

  DOI：10.1055/s-1999-3613

  日期：1999.11
• Synthesis of pyranonaphthoquinone antibiotics involving the ring closing metathesis of a vinyl ether
  作者：Tuyen Nguyen Van、Norbert De Kimpe

  DOI：10.1016/j.tetlet.2004.03.008

  日期：2004.4

  The synthesis of two antibiotic pyranonaphthoquinones was performed by a straightforward synthetic route utilizing ring closing metathesis. Vinylation of 3-(1-propenyl)-2-hydroxymethyl-1.4-dimethoxynapthalene under iridium catalysis and subsequent ring closing metathesis of 3-(1-propenyl)-2-vinyloxymethyl-1.4-dimethoxynaphthalene with Grubbs' catalyst paved the way to the natural antibiotics pentalongin and psychorubrin. (C) 2004 Elsevier Ltd. All rights reserved.