2,2,3a,10a-tetrahydro-5-methoxyfuro[2,3-b]naphtho[2,1-d]furan

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: 2,2,3a,10a-tetrahydro-5-methoxyfuro[2,3-b]naphtho[2,1-d]furan
• 英文别名: 8-Methoxy-14,16-dioxatetracyclo[8.6.0.02,7.011,15]hexadeca-1(10),2,4,6,8-pentaene；8-methoxy-14,16-dioxatetracyclo[8.6.0.02,7.011,15]hexadeca-1(10),2,4,6,8-pentaene
• 化学式: C₁₅H₁₄O₃
• 分子量: 242.274
• InChiKey: RCIXCSPNZQYNDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,3-二氢呋喃 、 4-甲氧基-1-萘酚 在 tetrabutylammonium tetrafluoroborate 作用下， 以 乙腈 为溶剂， 以39%的产率得到2,2,3a,10a-tetrahydro-5-methoxyfuro[2,3-b]naphtho[2,1-d]furan
  参考文献：
  名称：

  Anodic oxidation of 4-methoxy-1-naphthol

  摘要：

  Anodic oxidation of 4-methoxy-1-naphthol 1 in the presence of nucleophiles provided the corresponding products 8 - 12 and the dimers 13 and 17 were also produced. The reaction mechanism of the oxidation reaction including the [3 + 2] cycloaddition was investigated. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00544-0

文献信息

• Reactivity of naphthol towards nucleophiles in anodic oxidation
  作者：Hesham R El-Seedi、Shosuke Yamamura、Shigeru Nishiyama

  DOI：10.1016/s0040-4020(02)00829-3

  日期：2002.9

  Reactivity of the anodic oxidation of 4-methoxy-1-naphthol 1 in the presence of nucleophiles has been investigated. The reaction with electron-rich alkenic nucleophiles such as 1-methoxy-4-propenylbenzene 2 and isosafrole 3 gave a very high yield, whereas the reaction with dihydropyran 4 and dihydrofuran 5 gave a moderate yield, but with ethyl vinyl ether 6 gave a very low yield of the substituted dihydronaphthofuran derivatives 7-10 and 12, respectively. Unexpectedly, the glycosyl derivative 11 was preferentially produced rather than naphthofuran 10 upon using 5 as a nucleophile. In addition, the dimers 15 and 16 were obtained in moderate yield without addition of nucleophile to 1. The mechanism of the oxidation reactions including the [3+2] and [5+2] cycloaddition were discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Anodic oxidation of 4-methoxy-1-naphthol
  作者：Hesham R. El-Seedi、Shosuke Yamamura、Shigeru Nishiyama

  DOI：10.1016/s0040-4039(02)00544-0

  日期：2002.4

  Anodic oxidation of 4-methoxy-1-naphthol 1 in the presence of nucleophiles provided the corresponding products 8 - 12 and the dimers 13 and 17 were also produced. The reaction mechanism of the oxidation reaction including the [3 + 2] cycloaddition was investigated. (C) 2002 Elsevier Science Ltd. All rights reserved.