8-hydroxynaphtho[2,1-b]furan-1(2H)-one | 902759-37-9

• 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: 8-hydroxynaphtho[2,1-b]furan-1(2H)-one
• 英文别名: 8-Hydroxybenzo[e][1]benzofuran-1-one；8-hydroxybenzo[e][1]benzofuran-1-one
• CAS: 902759-37-9
• 化学式: C₁₂H₈O₃
• 分子量: 200.194
• InChiKey: USGTZMWFJVXDAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-hydroxynaphtho[2,1-b]furan-1(2H)-one 在 sodium tetrahydroborate 、 盐酸 作用下， 以 异丙醇 为溶剂， 反应 8.0h， 以45%的产率得到苯并[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
• 作为产物：
  描述：

  1-oxo-1,2-dihydronaphtho[2,1-b]furan-8-yl chloroacetate 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以85%的产率得到8-hydroxynaphtho[2,1-b]furan-1(2H)-one
  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

• [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.