N-(tert-butoxycarbonyl)-3-amino-2-(tri-n-butylstannyl)thiophene | 197370-07-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: N-(tert-butoxycarbonyl)-3-amino-2-(tri-n-butylstannyl)thiophene
• 英文别名: (2-Tri-n-butylstannyl-thiophen-3-yl)-carbamic acid tert-butyl ester；tert-butyl N-(2-tributylstannylthiophen-3-yl)carbamate
• CAS: 197370-07-3
• 化学式: C₂₁H₃₉NO₂SSn
• 分子量: 488.322
• InChiKey: NHUWGBFDEVEROT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.15
• 重原子数：
  26
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  66.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(tert-butoxycarbonyl)-3-amino-2-(tri-n-butylstannyl)thiophene 、 (2,5-dibromo-1,4-phenylene)bis((4-butylphenyl)methanone) 在 tris(dibenzylideneacetone)dipalladium (0) 、 三苯胂 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以89%的产率得到
  参考文献：
  名称：

  Imine-Bridged Planar Poly(phenylenethiophene)s and Polythiophenes

  摘要：

  Synthetic routes to soluble planar poly(phenylenethiophene)s and polythiophenes are described. The main polymer backbones are synthesized via Pd(0)-catalyzed couplings of the electron-rich N,N'-(bis-tert-butoxycarbonyl)-3,4-diamino-2,5-bis(tri-n-butylstannyl)thiophene with electron-deficient aryldibromodiones. The prebridged polymers have bathochromically shifted absorptions due to donor/acceptor interactions between the consecutive repeat units. Upon exposure of the polymers to trifluoroacetic acid or titanium tetrachloride, imine bridges are formed that force the consecutive units into planarity. The bridging units are sp(2)-hybridized, thus allowing for greater electron delocalization between the consecutive aryl units. The syntheses of model trimeric systems were conducted to provide further data for assessing the optical properties of the polymers. Protonation of the imine moieties causes bathochromic shifts of >100 nm in several cases. The effect is explained by an intramolecular charge transfer. Thus these arrangements of planar structures with imine bridges serve as optically based proton sensors with spectral shift differences far-exceeding those of nonplanar imine-containing polymers.

  DOI：

  10.1021/ja964223u
• 作为产物：
  描述：

  三丁基氯化锡 、 噻吩-3-氨基甲酸叔丁酯 在 正丁基锂 、 二异丙胺 作用下， 以 乙醚 为溶剂， 以82%的产率得到N-(tert-butoxycarbonyl)-3-amino-2-(tri-n-butylstannyl)thiophene
  参考文献：
  名称：

  Imine-Bridged Planar Poly(phenylenethiophene)s and Polythiophenes

  摘要：

  Synthetic routes to soluble planar poly(phenylenethiophene)s and polythiophenes are described. The main polymer backbones are synthesized via Pd(0)-catalyzed couplings of the electron-rich N,N'-(bis-tert-butoxycarbonyl)-3,4-diamino-2,5-bis(tri-n-butylstannyl)thiophene with electron-deficient aryldibromodiones. The prebridged polymers have bathochromically shifted absorptions due to donor/acceptor interactions between the consecutive repeat units. Upon exposure of the polymers to trifluoroacetic acid or titanium tetrachloride, imine bridges are formed that force the consecutive units into planarity. The bridging units are sp(2)-hybridized, thus allowing for greater electron delocalization between the consecutive aryl units. The syntheses of model trimeric systems were conducted to provide further data for assessing the optical properties of the polymers. Protonation of the imine moieties causes bathochromic shifts of >100 nm in several cases. The effect is explained by an intramolecular charge transfer. Thus these arrangements of planar structures with imine bridges serve as optically based proton sensors with spectral shift differences far-exceeding those of nonplanar imine-containing polymers.

  DOI：

  10.1021/ja964223u

文献信息

• Thiophene and furan compounds
  申请人：Castano Mansanet Maria Ana

  公开号：US20070105852A1

  公开（公告）日：2007-05-10

  The present invention relates to thiophene and furan compounds and their pharmaceutically acceptable salts, and further relates to their use in treating schizophrenia, cognitive deficits associated with schizophrenia, Alzheimer's disease, dementia of the Alzheimer's type, mild cognitive impairment, or depression.

  本发明涉及噻吩和呋喃化合物及其药学上可接受的盐，并进一步涉及它们在治疗精神分裂症、与精神分裂症相关的认知缺陷、阿尔茨海默病、阿尔茨海默型痴呆、轻度认知障碍或抑郁症中的应用。
• Zhang, Qing T.; Tour, James M., Journal of the American Chemical Society, 1998, vol. 120, # 22, p. 5355 - 5360
  作者：Zhang, Qing T.、Tour, James M.

  DOI：——

  日期：——