1,2-dihydronaphtho<2,1-b>furan-1,2-diol | 133523-53-2

• 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-dihydronaphtho<2,1-b>furan-1,2-diol
• 英文别名: 1,2-dihydronaphtho[2,1-b]furan-1,2-diol；1,2-Dihydrobenzo[e][1]benzofuran-1,2-diol
• CAS: 133523-53-2
• 化学式: C₁₂H₁₀O₃
• 分子量: 202.21
• InChiKey: GVIUQDPPBHGERW-UHFFFAOYSA-N

物化性质

• 熔点：
  61-62 °C(Solv: water (7732-18-5))
• 沸点：
  391.2±42.0 °C(Predicted)
• 密度：
  1.468±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,2-dihydronaphtho<2,1-b>furan-1,2-diol 在 盐酸 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以92%的产率得到萘并[2,1-b]呋喃-2(1H)-酮
  参考文献：
  名称：

  Base-catalyzed alkylation of 2-naphthol with glyoxal

  摘要：

  Alkylation of potassium 2-naphthyl oxide with glyoxal in aqueous media formed 1,2-dihydronaphtho[2,1-b]furan-1,2-diol (1). Without isolation of 1, acidification of this reaction mixture with aqueous HCl led to three products, i.e., the lactone of (2-hydroxy-1-naphthyl)acetic acid (2), the hemiacetal of bis(2-hydroxy-1-naphthyl)acetaldehyde (3), and the corresponding acetal (4). Mutual interconversions of 1 and these three products revealed the reaction pathway and the mechanisms of formation of the lactone and the acetal.

  DOI：

  10.1021/jo00010a029
• 作为产物：
  描述：

  草酸醛 、 2-萘酚 在 氢氧化钾 作用下， 以 水 为溶剂， 反应 3.0h， 以98%的产率得到1,2-dihydronaphtho<2,1-b>furan-1,2-diol
  参考文献：
  名称：

  Base-catalyzed alkylation of 2-naphthol with glyoxal

  摘要：

  Alkylation of potassium 2-naphthyl oxide with glyoxal in aqueous media formed 1,2-dihydronaphtho[2,1-b]furan-1,2-diol (1). Without isolation of 1, acidification of this reaction mixture with aqueous HCl led to three products, i.e., the lactone of (2-hydroxy-1-naphthyl)acetic acid (2), the hemiacetal of bis(2-hydroxy-1-naphthyl)acetaldehyde (3), and the corresponding acetal (4). Mutual interconversions of 1 and these three products revealed the reaction pathway and the mechanisms of formation of the lactone and the acetal.

  DOI：

  10.1021/jo00010a029

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。
• Preparation and Structural Properties of 7,8-Dioxa[6]helicenes and 7a,14c-Dihydro-7,8-dioxa[6]helicenes
  作者：Jørgen Eskildsen、Frederik C. Krebs、André Faldt、Peter Sommer-Larsen、Klaus Bechgaard

  DOI：10.1021/jo001312n

  日期：2001.1.1

  The potentially chiral 7,8-dioxa[6]helicenes 1-1c have been prepared by oxidation of their precursors the 7a,14c-dihydro-7,8-dioxa[6]helicenes 3. The crystal structure determination of 3b cis-7a,14c-dihydro-3,12-dibromo-7,8-dioxa[6]helicenes unambiguously confirms the cis configuration of the 7a,14c hydrogens in compounds 3 as previously implied from NMR measurements and also shows that; 3b crystallizes in a chiral conformation in the solid state. Selective deuteration of the sterically crowded 1,14 positions of 7,8-dioxal[6]helicene 1 influenced the crystal structure. The deuterium labeled compound D-2-1 exhibits a disordered structure, whereas 1 had been found to crystallize in a complex structure which can be described as an analogous partly ordered modulated superstructure. When dehydrogenation of compound 3 to obtain compound 1 was attempted, harsh synthetic conditions gave the unexpected halogenated compounds 5-chloro-7,8-dioxa[6]helicene 1c and cis-7a,14c-dibromo-7,8-dioxa[6]helicene 3c. Compounds 1d and 3b were identified by solving their crystal structure.
• 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.
• Fan, Xiaobo; Yamaye, Makoto; Kosugi, Yoshio, Journal of the Chemical Society. Perkin transactions II, 1994, # 9, p. 2001 - 2006
  作者：Fan, Xiaobo、Yamaye, Makoto、Kosugi, Yoshio、Okazaki, Hiroshi、Mizobe, Hoyou、et al.

  DOI：——

  日期：——
• KITO, TAKETOSHI;YOSHINAGA, KOHJI;YAMAYE, MAKOTO;MIZOBE, HOYOU, J. ORG. CHEM., 56,(1991) N0, C. 3336-3339
  作者：KITO, TAKETOSHI、YOSHINAGA, KOHJI、YAMAYE, MAKOTO、MIZOBE, HOYOU

  DOI：——

  日期：——