7-isopropoxynaphthalen-2-yl trifluoromethanesulfonate | 928153-25-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 7-isopropoxynaphthalen-2-yl trifluoromethanesulfonate
• CAS: 928153-25-7
• 化学式: C₁₄H₁₃F₃O₄S
• 分子量: 334.316
• InChiKey: VSDLFSGYYGCOPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.86
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  7-isopropoxynaphthalen-2-yl trifluoromethanesulfonate 在 氢氧化钾 、 1,2-双(二苯基膦)乙烷氯化镍 、 三溴化硼 作用下， 以 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 22.5h， 生成 1,5-Bis(2-hydroxy-7-propan-2-ylnaphthalen-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
• 作为产物：
  描述：

  三氟甲磺酸酐 、 7-isopropoxynaphthalen-2-ol 以 吡啶 为溶剂， 反应 0.5h， 以98%的产率得到7-isopropoxynaphthalen-2-yl trifluoromethanesulfonate
  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