2,3-naphtho-bis(6-chloro-1,4-dioxa)hexane | 89012-02-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,3-naphtho-bis(6-chloro-1,4-dioxa)hexane
• 英文别名: 2,3-Bis[2-(2-chloroethoxy)ethoxy]naphthalene
• CAS: 89012-02-2
• 化学式: C₁₈H₂₂Cl₂O₄
• 分子量: 373.276
• InChiKey: BORRIIPKWHJROG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  对甲苯磺酰胺 、 2,3-naphtho-bis(6-chloro-1,4-dioxa)hexane 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 以78%的产率得到2,3-naphtho-azacrown-5-p-toluenesulfonate
  参考文献：
  名称：

  FRET-derived ratiometric fluorescence sensor for Cu2+

  摘要：

  New N-(pyrenylmethyl)naphtho-azacrown-5 (1) was synthesized as an 'On-Off' fluorescent chemosensor for Cu2+. Excited at 240 nm corresponding to the absorption of naphthalene unit (energy donor) of 1, emission at 380 nm from pyrene unit (energy acceptor) is observed, indicating that intramolecular fluorescence resonance energy transfer (FRET-On) occurs in 1. When Cu2+ is added to a solution of 1, however, the fluorescence of pyrene is strongly quenched (FRET-Off) whereas that of naphthalene group is revived. Such FRET 'On-Off' behavior of 1 is observed only in the case of Cu2+ binding, but not for other metal cations. The high selectivity of 1 toward Cu2+ can be potentially applied to a new kind of FRET-based chemosensor. The FRET On-Off behavior is supported by computational studies. The calculated molecular orbitals of HOMO and LUMOs suggest the excited-state interactions leading to FRET from naphthalene to pyrene in 1, but no electron density changes in 1.Cu2+ complex. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.11.063
• 作为产物：
  描述：

  2-(2-chloroethoxy)ethyl tosylate 、 2,3-二羟基萘 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 生成 2,3-naphtho-bis(6-chloro-1,4-dioxa)hexane
  参考文献：
  名称：

  FRET-derived ratiometric fluorescence sensor for Cu2+

  摘要：

  New N-(pyrenylmethyl)naphtho-azacrown-5 (1) was synthesized as an 'On-Off' fluorescent chemosensor for Cu2+. Excited at 240 nm corresponding to the absorption of naphthalene unit (energy donor) of 1, emission at 380 nm from pyrene unit (energy acceptor) is observed, indicating that intramolecular fluorescence resonance energy transfer (FRET-On) occurs in 1. When Cu2+ is added to a solution of 1, however, the fluorescence of pyrene is strongly quenched (FRET-Off) whereas that of naphthalene group is revived. Such FRET 'On-Off' behavior of 1 is observed only in the case of Cu2+ binding, but not for other metal cations. The high selectivity of 1 toward Cu2+ can be potentially applied to a new kind of FRET-based chemosensor. The FRET On-Off behavior is supported by computational studies. The calculated molecular orbitals of HOMO and LUMOs suggest the excited-state interactions leading to FRET from naphthalene to pyrene in 1, but no electron density changes in 1.Cu2+ complex. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.11.063

文献信息

• Synthesis, characterization and solid-phase 13C NMR of naphtho-9-crown-3
  作者：A Moghimi、M.F Rastegar、M Ghandi、G.W Buchanan、H Rahbarnoohi

  DOI：10.1016/s0022-2860(00)00462-2

  日期：2000.8

  The synthesis and characterization of naptho-9-crown-3, N9C3, as a novel 9-membered ring crown ether with greater lipophilicity than that of benzo-9-crown-3, B9C3, is reported. The solution AA'BB' pattern of -CH2O- protons in N9C3 is close to that of B9C3. The solid-phase C-13 CPMAS NMR, as a tool for conformation prediction, reveals that the solid-phase conformation of the 9-membered ring crown cavity in N9C3 is different from B9C3, the two key C2O2CH(2) and C3O1CH(2) units are predicted to be out of naphthalene plane, and the two C1C2O2CH(2) and C4C3O1CH(2) torsion angles are close to each other. (C) 2000 Elsevier Science B.V. All rights reserved.
• CZECH, B.;CZECH, A.;BARTSCH, R. A., ORG. PREP. AND PROCED. INT., 1983, 15, N 5, 349-359
  作者：CZECH, B.、CZECH, A.、BARTSCH, R. A.

  DOI：——

  日期：——
• US5136033A
  申请人：——

  公开号：US5136033A

  公开（公告）日：1992-08-04
• FRET-derived ratiometric fluorescence sensor for Cu2+
  作者：Hyun Jung Kim、Sun Young Park、Sangwoon Yoon、Jong Seung Kim

  DOI：10.1016/j.tet.2007.11.063

  日期：2008.2

  New N-(pyrenylmethyl)naphtho-azacrown-5 (1) was synthesized as an 'On-Off' fluorescent chemosensor for Cu2+. Excited at 240 nm corresponding to the absorption of naphthalene unit (energy donor) of 1, emission at 380 nm from pyrene unit (energy acceptor) is observed, indicating that intramolecular fluorescence resonance energy transfer (FRET-On) occurs in 1. When Cu2+ is added to a solution of 1, however, the fluorescence of pyrene is strongly quenched (FRET-Off) whereas that of naphthalene group is revived. Such FRET 'On-Off' behavior of 1 is observed only in the case of Cu2+ binding, but not for other metal cations. The high selectivity of 1 toward Cu2+ can be potentially applied to a new kind of FRET-based chemosensor. The FRET On-Off behavior is supported by computational studies. The calculated molecular orbitals of HOMO and LUMOs suggest the excited-state interactions leading to FRET from naphthalene to pyrene in 1, but no electron density changes in 1.Cu2+ complex. (c) 2007 Elsevier Ltd. All rights reserved.