(R)-(-)-[9,9']bi[naphtho[2,1-b]furanyl]-8,8'-diol

• 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: (R)-(-)-[9,9']bi[naphtho[2,1-b]furanyl]-8,8'-diol
• 英文别名: 9-(8-Hydroxybenzo[e][1]benzofuran-9-yl)benzo[e][1]benzofuran-8-ol
• 化学式: C₂₄H₁₄O₄
• 分子量: 366.373
• InChiKey: LSWFRDVCGWNTOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-(-)-[9,9']bi[naphtho[2,1-b]furanyl]-8,8'-diol 在 lithium aluminium tetrahydride 、 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 7,15,18,21,24,27,30,38-Octaoxaheptacyclo[29.11.0.02,14.03,11.04,8.034,42.037,41]dotetraconta-1(31),2(14),3(11),4(8),5,9,12,32,34(42),35,37(41),39-dodecaene
  参考文献：
  名称：

  基于熔融BINOL的冠作为荧光手性传感器，用于对苯乙胺和缬氨酸乙酯的对映选择性识别

  摘要：

  开发了一种基于呋喃酚的BINOL的手性冠，作为对苯乙胺和缬氨酸乙酯的对映选择性手性传感器。呋喃与BINOL的融合产生了高度立体区分的骨架，用于开发的手性冠。该手性冠在苯乙胺的两个对映异构体之间显示出2.97倍的发荧光增强差异，在缬氨酸乙酯的两个对映异构体之间显示出2.55倍的荧光增强差。发现苯乙胺的两个对映异构体的两个非对映体复合物的缔合常数之比为11.30，缬氨酸乙酯的两个对映异构体之比为7.02。

  DOI：

  10.1021/jo070850y
• 作为产物：
  描述：

  8-hydroxynaphtho[2,1-b]furan-1(2H)-one 在 sodium tetrahydroborate 、 n-benzylcinchonidinium chloride 、 三氯化铁 作用下， 以 水 、 异丙醇 、 乙腈 为溶剂， 反应 12.08h， 生成 (R)-(-)-[9,9']bi[naphtho[2,1-b]furanyl]-8,8'-diol
  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.
• [9,9′]Bi[naphtho(2,1-b)furanyl]-8,8′-diol, a furo-fused BINOL derivative: synthesis, resolution and determination of absolute configuration
  作者：Anil V. Karnik、Sunil P. Upadhyay、Manish G. Gangrade

  DOI：10.1016/j.tetasy.2006.04.017

  日期：2006.4

  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.
• Furo-Fused BINOL Based Crown as a Fluorescent Chiral Sensor for Enantioselective Recognition of Phenylethylamine and Ethyl Ester of Valine
  作者：Sunil P. Upadhyay、Raghuvir R. S. Pissurlenkar、Evans C. Coutinho、Anil V. Karnik

  DOI：10.1021/jo070850y

  日期：2007.7.1

  A furo-fused BINOL based chiral crown was developed as an enantioselective chiral sensor for phenylethylamine and ethyl ester of valine. Fusion of furan to BINOL has resulted in a highly stereo-discriminating backbone for the chiral crown developed. This chiral crown exhibited a flourescence enhancement difference of 2.97 times between two enantiomers of phenylethylamine and 2.55 times between two

  开发了一种基于呋喃酚的BINOL的手性冠，作为对苯乙胺和缬氨酸乙酯的对映选择性手性传感器。呋喃与BINOL的融合产生了高度立体区分的骨架，用于开发的手性冠。该手性冠在苯乙胺的两个对映异构体之间显示出2.97倍的发荧光增强差异，在缬氨酸乙酯的两个对映异构体之间显示出2.55倍的荧光增强差。发现苯乙胺的两个对映异构体的两个非对映体复合物的缔合常数之比为11.30，缬氨酸乙酯的两个对映异构体之比为7.02。