3-vinyl-naphthalene-2-amine

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-vinyl-naphthalene-2-amine
• 英文别名: 3-Ethenylnaphthalen-2-amine
• 化学式: C₁₂H₁₁N
• 分子量: 169.226
• InChiKey: HNHVVILEILQGIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-vinyl-naphthalene-2-amine 在 lithium aluminium tetrahydride 、 溴 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 56.5h， 生成
  参考文献：
  名称：

  Two BN Isosteres of Anthracene: Synthesis and Characterization

  摘要：

  The synthesis of two parental BN anthracenes, 1 and 2, was developed, and their electronic structure and reactivity behavior were characterized in direct comparison with all-carbon anthracene. Gas-phase UV-photoelecton spectroscopy studies revealed the following HOMO energy trend: anthracene, -7.4 eV; BN anthracene 1, -7.7 eV; bis-BN anthracene 2, -8.0 eV. The ?max of the lower energy band in the UV-vis absorption spectrum is as follows: anthracene, 356 nm; BN anthracene 1, 359 nm; bis-BN anthracene 2, 357 nm. Thus, although the HOMO is stabilized with increasing BN incorporation, the HOMO-LUMO band gap remains unchanged across the anthracene series. The emission ?max values for the three investigated anthracene compounds are at 403 nm. The pKa values of the N-H proton for BN anthracene 1 and bis-BN anthracene 2 were determined to be approximately 26. BN anthracenes 1 and 2 do not undergo heat- or light-induced cycloaddition reactions or Friedel-Crafts acylations. Electrophilic bromination of BN anthracene 1 with Br2, however, occurs regioselectively at the 9-position. The reactivity behavior and regioselectivity of bromination of BN anthracenes are consistent with the electronic structure of these compounds; i.e., (1) the lower HOMO energy levels for BN anthracenes stabilize the molecules against cycloaddition and Friedel-Crafts reactions, and (2) the HOMO orbital coefficients are consistent with the observed bromination regioselectivity. Overall, this work demonstrates that BN/CC isosterism can be used as a molecular design strategy to stabilize the HOMO of acene-type structures while the optical band gap is maintained.

  DOI：

  10.1021/ja508813v
• 作为产物：
  描述：

  3-碘萘-2-羧酸 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 叠氮磷酸二苯酯 、 三乙胺 作用下， 以 丙醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 22.0h， 生成 3-vinyl-naphthalene-2-amine
  参考文献：
  名称：

  Two BN Isosteres of Anthracene: Synthesis and Characterization

  摘要：

  The synthesis of two parental BN anthracenes, 1 and 2, was developed, and their electronic structure and reactivity behavior were characterized in direct comparison with all-carbon anthracene. Gas-phase UV-photoelecton spectroscopy studies revealed the following HOMO energy trend: anthracene, -7.4 eV; BN anthracene 1, -7.7 eV; bis-BN anthracene 2, -8.0 eV. The ?max of the lower energy band in the UV-vis absorption spectrum is as follows: anthracene, 356 nm; BN anthracene 1, 359 nm; bis-BN anthracene 2, 357 nm. Thus, although the HOMO is stabilized with increasing BN incorporation, the HOMO-LUMO band gap remains unchanged across the anthracene series. The emission ?max values for the three investigated anthracene compounds are at 403 nm. The pKa values of the N-H proton for BN anthracene 1 and bis-BN anthracene 2 were determined to be approximately 26. BN anthracenes 1 and 2 do not undergo heat- or light-induced cycloaddition reactions or Friedel-Crafts acylations. Electrophilic bromination of BN anthracene 1 with Br2, however, occurs regioselectively at the 9-position. The reactivity behavior and regioselectivity of bromination of BN anthracenes are consistent with the electronic structure of these compounds; i.e., (1) the lower HOMO energy levels for BN anthracenes stabilize the molecules against cycloaddition and Friedel-Crafts reactions, and (2) the HOMO orbital coefficients are consistent with the observed bromination regioselectivity. Overall, this work demonstrates that BN/CC isosterism can be used as a molecular design strategy to stabilize the HOMO of acene-type structures while the optical band gap is maintained.

  DOI：

  10.1021/ja508813v

文献信息

• SUBSTITUTED 1,2-AZABORINE HETEROCYCLES
  申请人：State of Oregon acting by & through the State Board of Higher Eduction on behalf of the University of Oregon

  公开号：EP2459573A1

  公开（公告）日：2012-06-06
• US8921554B2
  申请人：——

  公开号：US8921554B2

  公开（公告）日：2014-12-30
• [EN] SUBSTITUTED 1,2-AZABORINE HETEROCYCLES<br/>[FR] HÉTÉROCYCLES DE 1,2-AZABORINE SUBSTITUÉS
  申请人：STATE OF OREGON ON BEHALF OF THE UNIVERSITY OF OREGON

  公开号：WO2011017129A1

  公开（公告）日：2011-02-10

  Aromatic heterocycles incorporating boron and nitrogen atoms, in particular, 1,2-azaborine compounds having the formula (I) and their use as synthetic intermediates.
• Two BN Isosteres of Anthracene: Synthesis and Characterization
  作者：Jacob S. A. Ishibashi、Jonathan L. Marshall、Audrey Mazière、Gabriel J. Lovinger、Bo Li、Lev N. Zakharov、Alain Dargelos、Alain Graciaa、Anna Chrostowska、Shih-Yuan Liu

  DOI：10.1021/ja508813v

  日期：2014.10.29

  The synthesis of two parental BN anthracenes, 1 and 2, was developed, and their electronic structure and reactivity behavior were characterized in direct comparison with all-carbon anthracene. Gas-phase UV-photoelecton spectroscopy studies revealed the following HOMO energy trend: anthracene, -7.4 eV; BN anthracene 1, -7.7 eV; bis-BN anthracene 2, -8.0 eV. The ?max of the lower energy band in the UV-vis absorption spectrum is as follows: anthracene, 356 nm; BN anthracene 1, 359 nm; bis-BN anthracene 2, 357 nm. Thus, although the HOMO is stabilized with increasing BN incorporation, the HOMO-LUMO band gap remains unchanged across the anthracene series. The emission ?max values for the three investigated anthracene compounds are at 403 nm. The pKa values of the N-H proton for BN anthracene 1 and bis-BN anthracene 2 were determined to be approximately 26. BN anthracenes 1 and 2 do not undergo heat- or light-induced cycloaddition reactions or Friedel-Crafts acylations. Electrophilic bromination of BN anthracene 1 with Br2, however, occurs regioselectively at the 9-position. The reactivity behavior and regioselectivity of bromination of BN anthracenes are consistent with the electronic structure of these compounds; i.e., (1) the lower HOMO energy levels for BN anthracenes stabilize the molecules against cycloaddition and Friedel-Crafts reactions, and (2) the HOMO orbital coefficients are consistent with the observed bromination regioselectivity. Overall, this work demonstrates that BN/CC isosterism can be used as a molecular design strategy to stabilize the HOMO of acene-type structures while the optical band gap is maintained.