1,2,6,7-Tetrahydronaphtho<2,1-b:6,5-b'>difuran-1,2,6,7-tetraol | 166529-71-1

• 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: 1,2,6,7-Tetrahydronaphtho<2,1-b:6,5-b'>difuran-1,2,6,7-tetraol
• 英文别名: 2,3,7,8-Tetrahydro-[1]benzofuro[5,4-e][1]benzofuran-2,3,7,8-tetrol
• CAS: 166529-71-1
• 化学式: C₁₄H₁₂O₆
• 分子量: 276.246
• InChiKey: WERHKEORQKVZHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,2,6,7-Tetrahydronaphtho<2,1-b:6,5-b'>difuran-1,2,6,7-tetraol 在 甲烷磺酸 作用下， 以 乙二醇二甲醚 为溶剂， 反应 24.0h， 以33%的产率得到1,2,6,7-Tetrahydro-2,7-dioxonaphtho<2,1-b><6,5-b'>difuran
  参考文献：
  名称：

  Aromatic Compounds with a 3a,6a-Dihydrofuro[2,3-b]furan Moiety. 2. Alkylation Products of Dihydroxynaphthalenes with 1,2-Dihydronaphtho[2,3-b]furan-1,2-diol and Their Structure Analyses

  摘要：

  The alkylation of 2,3-, 2,6-, and 2,7-dihydroxynaphthalenes (DHN) with 1,2-dihydronaphtho[2,1-b]furan-1,2-diol (1) in an acidic condition gave various products derived from 7a,14c-dihydronaphtho[2,1-b]naphtho[1',2':4,5]furo[3,2-d]furan (2a). The products were characterized mainly by NMR spectroscopy with the help of the MNDO MO method. The reaction proceeds via two steps. The hydroxyl group-substituted 2a first formed depending on the starting DHN. These 2a derivatives reacted with another mole of 1 to give the corresponding products with two 3a,6a-dihydrofuro[2,3-b]furan moieties. The product from 2,7-DHN, however, formed in a poor yield, accompanying an unexpected 2a derivative, due to a severe steric hindrance. Another method to prepare these compounds was examined using new precursors with four hydroxyl groups, corresponding to 1.

  DOI：

  10.1021/jo00122a016
• 作为产物：
  描述：

  2,6-萘二酚 、 草酸醛 在 氢氧化钾 作用下， 反应 5.0h， 以99%的产率得到1,2,6,7-Tetrahydronaphtho<2,1-b:6,5-b'>difuran-1,2,6,7-tetraol
  参考文献：
  名称：

  Aromatic Compounds with a 3a,6a-Dihydrofuro[2,3-b]furan Moiety. 2. Alkylation Products of Dihydroxynaphthalenes with 1,2-Dihydronaphtho[2,3-b]furan-1,2-diol and Their Structure Analyses

  摘要：

  The alkylation of 2,3-, 2,6-, and 2,7-dihydroxynaphthalenes (DHN) with 1,2-dihydronaphtho[2,1-b]furan-1,2-diol (1) in an acidic condition gave various products derived from 7a,14c-dihydronaphtho[2,1-b]naphtho[1',2':4,5]furo[3,2-d]furan (2a). The products were characterized mainly by NMR spectroscopy with the help of the MNDO MO method. The reaction proceeds via two steps. The hydroxyl group-substituted 2a first formed depending on the starting DHN. These 2a derivatives reacted with another mole of 1 to give the corresponding products with two 3a,6a-dihydrofuro[2,3-b]furan moieties. The product from 2,7-DHN, however, formed in a poor yield, accompanying an unexpected 2a derivative, due to a severe steric hindrance. Another method to prepare these compounds was examined using new precursors with four hydroxyl groups, corresponding to 1.

  DOI：

  10.1021/jo00122a016

文献信息

• Aromatic Compounds with a 3a,6a-Dihydrofuro[2,3-b]furan Moiety. 2. Alkylation Products of Dihydroxynaphthalenes with 1,2-Dihydronaphtho[2,3-b]furan-1,2-diol and Their Structure Analyses
  作者：Xiaobo Fan、Tomoko Yanai、Hiroshi Okazaki、Makoto Yamaye、Hoyou Mizobe、Yoshio Kosugi、Taketoshi Kito

  DOI：10.1021/jo00122a016

  日期：1995.9

  The alkylation of 2,3-, 2,6-, and 2,7-dihydroxynaphthalenes (DHN) with 1,2-dihydronaphtho[2,1-b]furan-1,2-diol (1) in an acidic condition gave various products derived from 7a,14c-dihydronaphtho[2,1-b]naphtho[1',2':4,5]furo[3,2-d]furan (2a). The products were characterized mainly by NMR spectroscopy with the help of the MNDO MO method. The reaction proceeds via two steps. The hydroxyl group-substituted 2a first formed depending on the starting DHN. These 2a derivatives reacted with another mole of 1 to give the corresponding products with two 3a,6a-dihydrofuro[2,3-b]furan moieties. The product from 2,7-DHN, however, formed in a poor yield, accompanying an unexpected 2a derivative, due to a severe steric hindrance. Another method to prepare these compounds was examined using new precursors with four hydroxyl groups, corresponding to 1.