1,5-Bis(2-hydroxy-7-prop-2-enoxynaphthalen-1-yl)naphthalene-2,6-diol | 928160-31-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,5-Bis(2-hydroxy-7-prop-2-enoxynaphthalen-1-yl)naphthalene-2,6-diol
• 英文别名: 1,5-bis(2-hydroxy-7-prop-2-enoxynaphthalen-1-yl)naphthalene-2,6-diol
• CAS: 928160-31-0
• 化学式: C₃₆H₂₈O₆
• 分子量: 556.615
• InChiKey: BUDKGQXAERWAIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  42
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  1,5-Bis(2-hydroxy-7-prop-2-enoxynaphthalen-1-yl)naphthalene-2,6-diol 在 Grubbs catalyst first generation 作用下， 以 苯 为溶剂， 反应 5.0h， 以97%的产率得到(22Z)-20,25-dioxaheptacyclo[24.6.2.216,19.02,7.06,11.012,17.029,33]hexatriaconta-1(32),2,4,6,8,10,12,14,16,18,22,26(34),27,29(33),30,35-hexadecaene-3,10,13,32-tetrol
  参考文献：
  名称：

  Rapid atropisomerization of 1,1′:5′,1″-ternaphthalene-2,2′,6′,2″-tetrol (TERNOL) and its inhibition by tethering at positions 7 and 7″

  摘要：

  Atropisomerization of 1,1':5',1"-temaphthalene-2,2',6',2"-tetrol (TERNOL) is very fast under basic conditions. The stereochemical instability is attributed to the nature of oxide anion of the central 2,6-naphthodiol moiety. Ring-closing metathesis of 7,7"-diallyloxy TERNOL results in intramolecular tethering in a high yield, which intrinsically inhibits the rapid isomerization. Bidentate sites in the tethered TERNOL are proved to have enough structural flexibility as an axial chiral ligand. (c) 2006 Elsevier Ltd, All rights reserved.

  DOI：

  10.1016/j.tet.2006.12.046
• 作为产物：
  描述：

  1,5-二溴萘-2,6-二醇 、 7-(allyloxy)naphthalen-2-ol 在 氢氧化钾 作用下， 以 水 为溶剂， 反应 72.0h， 以44%的产率得到1,5-Bis(2-hydroxy-7-prop-2-enoxynaphthalen-1-yl)naphthalene-2,6-diol
  参考文献：
  名称：

  Rapid atropisomerization of 1,1′:5′,1″-ternaphthalene-2,2′,6′,2″-tetrol (TERNOL) and its inhibition by tethering at positions 7 and 7″

  摘要：

  Atropisomerization of 1,1':5',1"-temaphthalene-2,2',6',2"-tetrol (TERNOL) is very fast under basic conditions. The stereochemical instability is attributed to the nature of oxide anion of the central 2,6-naphthodiol moiety. Ring-closing metathesis of 7,7"-diallyloxy TERNOL results in intramolecular tethering in a high yield, which intrinsically inhibits the rapid isomerization. Bidentate sites in the tethered TERNOL are proved to have enough structural flexibility as an axial chiral ligand. (c) 2006 Elsevier Ltd, All rights reserved.

  DOI：

  10.1016/j.tet.2006.12.046

文献信息

• Rapid atropisomerization of 1,1′:5′,1″-ternaphthalene-2,2′,6′,2″-tetrol (TERNOL) and its inhibition by tethering at positions 7 and 7″
  作者：Takashi Sugimura、Naohiro Matsushita、Keiko Minokami、Shinya Kurita

  DOI：10.1016/j.tet.2006.12.046

  日期：2007.2

  Atropisomerization of 1,1':5',1"-temaphthalene-2,2',6',2"-tetrol (TERNOL) is very fast under basic conditions. The stereochemical instability is attributed to the nature of oxide anion of the central 2,6-naphthodiol moiety. Ring-closing metathesis of 7,7"-diallyloxy TERNOL results in intramolecular tethering in a high yield, which intrinsically inhibits the rapid isomerization. Bidentate sites in the tethered TERNOL are proved to have enough structural flexibility as an axial chiral ligand. (c) 2006 Elsevier Ltd, All rights reserved.