1,2,9,10-Tetrahydronaphtho<2,1-b:7,8-b'>difuran-1,2,9,10-tetraol | 166529-72-2

• 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: 1,2,9,10-Tetrahydronaphtho<2,1-b:7,8-b'>difuran-1,2,9,10-tetraol
• 英文别名: 1,2,9,10-tetrahydronaphtho<2,1-b;7,8-b'>difuran-1,2,9,10-tetrol；1,2,9,10-tetrahydronaphtho[2,1-b:7,8-b']difuran-1,2,9,10-tetraol；5,13-Dioxatetracyclo[7.7.0.02,6.012,16]hexadeca-1(9),2(6),7,10,12(16)-pentaene-3,4,14,15-tetrol
• CAS: 166529-72-2
• 化学式: C₁₄H₁₂O₆
• 分子量: 276.246
• InChiKey: ODUXUOOLLCOIHX-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：

  1,2,9,10-Tetrahydronaphtho<2,1-b:7,8-b'>difuran-1,2,9,10-tetraol 在 盐酸 、 甲烷磺酸 、 水 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 18.0h， 生成 (15S,23S)-19,21-dimethyl-6,14,16-trioxahexacyclo[11.10.0.02,10.03,7.015,23.017,22]tricosa-1(13),2(10),3(7),8,11,17,19,21-octaen-5-one
  参考文献：
  名称：

  Preparation and Optical Resolution of a New Helical Lactone Carrying the 2,8-Dioxabicyclo[3.3.0]octane Ring System

  摘要：

  A new overcrowded lactone (3) carrying the 2,8-dioxabicyclo [3.3.0] octane ring system was prepared by a simple treatment of tetraol (1) (prepared from 2,7-dihydroxynaphthalene and glyoxal) with 3,5-xylenol, and readily resolved into its enantiomers having a specific rotation of >800degrees (absolute value). A preliminary experiment demonstrated that 3 would be a promising resolving agent.

  DOI：

  10.3987/com-03-9919
• 作为产物：
  描述：

  草酸醛 、 2,7-二羟基萘 在 氢氧化钾 作用下， 反应 3.0h， 以60%的产率得到1,2,9,10-Tetrahydronaphtho<2,1-b:7,8-b'>difuran-1,2,9,10-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

• Preparation and Stereochemistry of the Isopropylidene Derivatives of 1,2‐Dihydronaphtho[2,1‐<i>b</i>]Furan‐1,2‐Diol and 1,2,9,10‐Tetrahydronaphtho[2,1‐<i>b</i>:7,8‐<i>b</i>′] Difuran‐1,2,9,10‐Tetraol in Comparison with the Corresponding Acetyl Derivatives
  作者：Makoto Yamaye、Yoshiko Motoyanagi、Aya Nakagawa、Sanae Kametani、Tetsutaro Yoshinaga、Namiko Cho (Toh)、Xiaobo Fan、Taketoshi Kito

  DOI：10.1081/scc-200039376

  日期：2004.12.31

  10‐tetrahydronaphtho[2,1‐b:7,8‐b′]difuran‐1,2,9,10‐tetraol were transformed into the corresponding isopropylidene derivatives, which were studied mainly by 1H NMR and chiral HPLC analyses in terms of a possible transformation mechanism and stereochemistry in comparison with their corresponding acetyl derivatives.

  摘要 1,2-Dihydronaphtho[2,1-b]furan-1,2-diol 和 1,2,9,10-tetrahydronaphtho[2,1-b:7,8-b']difuran-1,2, 9,10-四醇转化为相应的异亚丙基衍生物，主要通过 1H NMR 和手性 HPLC 分析研究其可能的转化机制和立体化学，并与其相应的乙酰衍生物进行比较。
• 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.
• Preparation and Optical Resolution of a New Helical Lactone Carrying the 2,8-Dioxabicyclo[3.3.0]octane Ring System
  作者：Makoto Yamaye、Yusuke Ikeda、Namiko Cho(Toh)、Yoshinori Miura、Tetsutaro Yoshinaga、Katsuya Mukae、Toshiaki Tsuru

  DOI：10.3987/com-03-9919

  日期：——

  A new overcrowded lactone (3) carrying the 2,8-dioxabicyclo [3.3.0] octane ring system was prepared by a simple treatment of tetraol (1) (prepared from 2,7-dihydroxynaphthalene and glyoxal) with 3,5-xylenol, and readily resolved into its enantiomers having a specific rotation of >800degrees (absolute value). A preliminary experiment demonstrated that 3 would be a promising resolving agent.
• Fan, Xiaobo; Yanai, Tomoko; Yamaye, Makoto, Journal of Chemical Research, Miniprint, 1998, # 7, p. 1538 - 1548
  作者：Fan, Xiaobo、Yanai, Tomoko、Yamaye, Makoto、Okazaki, Hiroshi、Kito, Taketoshi

  DOI：——

  日期：——