苯并[e][1]苯并呋喃-8-醇 | 86539-49-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 中文名称: 苯并[e][1]苯并呋喃-8-醇
• 英文名称: naphtho[2,1-b]furan-8-ol
• 英文别名: benzo[e][1]benzofuran-8-ol
• CAS: 86539-49-3
• 化学式: C₁₂H₈O₂
• 分子量: 184.194
• InChiKey: VGADWSLIPYCKHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  33.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  苯并[e][1]苯并呋喃-8-醇 在 硫酸 、 硝酸 作用下， 以 乙酸酐 为溶剂， 反应 3.0h， 生成 acetoxy-7 nitro-2 naphto(2,1-b)furanne
  参考文献：
  名称：

  Buisson; Lamotte; Demerseman, European Journal of Medicinal Chemistry, 1983, vol. 18, # 2, p. 169 - 174

  摘要：

  DOI：
• 作为产物：
  描述：

  1-oxo-1,2-dihydronaphtho[2,1-b]furan-8-yl chloroacetate 在 盐酸 、 sodium tetrahydroborate 作用下， 以 甲醇 、 异丙醇 为溶剂， 反应 11.0h， 生成 苯并[e][1]苯并呋喃-8-醇
  参考文献：
  名称：

  [9,9′]Bi[naphtho(2,1-b)furanyl]-8,8′-diol, a furo-fused BINOL derivative: synthesis, resolution and determination of absolute configuration

  摘要：

  A high yielding synthetic protocol was employed in order to achieve the placement of a furan ring at the most sterically crucial position of BINOL to obtain [9,9]bi[naphtha(2,1-b)furanyl]-8,8'-diol. The racemate was resolved and the configuration of one of the enantiomers was found by single crystal X-ray analysis of a Mosher's acid diester derivative. This furo-fused BINOL derivative exhibited modified steric and electronic properties. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.04.017

文献信息

• Enantioselective synthesis of (R) and (S)-[9,9′]bi[naphtho(2,1-b)furanyl]-8,8′-diol: a furo-fused BINOL derivative
  作者：Sunil P. Upadhyay、Anil V. Karnik

  DOI：10.1016/j.tetlet.2006.11.006

  日期：2007.1

  The en antioselective synthesis of [9,9']bi[naphtho(2,1-b)furanyl]-8,8'-diol, a modified BINOL, was achieved using an inexpensive route. Both enantiomers of [9,9']bi[naphtho(2,1-b)furanyl]-8,8'-diol were obtained with satisfactory stereo selectivities by employing two optical antipodes of plienylethylamine as chiral influence in a Cu(II)Cl-2 catalyzed oxidative coupling step. (c) 2006 Elsevier Ltd. All rights reserved.
• Directional Approach to Enantiomerically Enriched Functionalized [7]Oxa-helicenoids and Groove-Based Selective Cyanide Sensing
  作者：Vaibhav N. Khose、Mohammed Hasan、Sushil C. Khot、Shaikh M. Mobin、Victor Borovkov、Anil V. Karnik

  DOI：10.1021/acs.joc.9b02100

  日期：2020.2.21

  Several regioselective functionalized mono- and disubstituted [7]oxa-helicenoids have been synthesized in the enantiomerically enriched (90-99% ee) form. These functionalized helicenoids exhibited pronounced spectral and chiroptical properties suitable for sensing applications. In particular, corresponding helicenoid's mono and dialdehydes have been effectively used as chemodosimeters for selective detection of cyanide anions over other anions, while simple aromatic aldehydes do not function as cyanide sensors. The groove available in the helical host plays a crucial role in the sensing. The enantiomerically enriched nature of the sensors allows the use of electronic circular dichroism as an uncommon detection tool for cyanide anions, along with conventional fluorescence and NMR methods.