5-<3'-(5''-acetoxy-1''-hydroxyhexylene)-1',2',3',4'-tetrahydro-1',4'-dioxonaphth-2'-yl>furan-2(5H)-one | 140860-71-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-<3'-(5''-acetoxy-1''-hydroxyhexylene)-1',2',3',4'-tetrahydro-1',4'-dioxonaphth-2'-yl>furan-2(5H)-one
• CAS: 140860-71-5；140860-73-7
• 化学式: C₂₂H₂₂O₇
• 分子量: 398.412
• InChiKey: VOMAHLBAWLFEFR-MNDPQUGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  106.97
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  三甲硅氧基-2-呋喃 、 Acetic acid 5-(1,4-dioxo-1,4-dihydro-naphthalen-2-yl)-1-methyl-5-oxo-pentyl ester 以 乙腈 为溶剂， 反应 1.0h， 以80%的产率得到5-<3'-(5''-acetoxy-1''-hydroxyhexylene)-1',2',3',4'-tetrahydro-1',4'-dioxonaphth-2'-yl>furan-2(5H)-one
  参考文献：
  名称：

  Synthesis of a pyranonaphthoquinone-spiroacetal

  摘要：

  A synthesis of pyranonaphthoquinone spiroacetal 12 is reported which represents an efficient entry to the pentacyclic framework of the pyranonaphthoquinone antibiotic griseusin A. The key step involves assembly of the furo[3,2-b]naphtho[2,3-d]pyran 11 via a ceric ammonium nitrate oxidative rearrangement of the furo[3,2-b]naptho[2,1-d]furan 10. This latter heterocycle 10 in turn was constructed via the uncatalysed 1,4-addition of 2 trimethylsilyloxyfuran 9 to naphthoquinone 8. Naphthoquinone 8 is readily available from 1,4 dimethoxynaphthalene-2-carbaldehyde 3 and acetylene 4.

  DOI：

  10.1039/p19920000579

文献信息

• Synthesis of a pyranonaphthoquinone-spiroacetal
  作者：Margaret A. Brimble、Michael R. Nairn

  DOI：10.1039/p19920000579

  日期：——

  A synthesis of pyranonaphthoquinone spiroacetal 12 is reported which represents an efficient entry to the pentacyclic framework of the pyranonaphthoquinone antibiotic griseusin A. The key step involves assembly of the furo[3,2-b]naphtho[2,3-d]pyran 11 via a ceric ammonium nitrate oxidative rearrangement of the furo[3,2-b]naptho[2,1-d]furan 10. This latter heterocycle 10 in turn was constructed via the uncatalysed 1,4-addition of 2 trimethylsilyloxyfuran 9 to naphthoquinone 8. Naphthoquinone 8 is readily available from 1,4 dimethoxynaphthalene-2-carbaldehyde 3 and acetylene 4.