3-(Trimethylacetamido)-2-naphthaldehyde | 154845-27-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(Trimethylacetamido)-2-naphthaldehyde
• 英文别名: N-(3-formylnaphthalen-2-yl)-2,2-dimethylpropanamide
• CAS: 154845-27-9
• 化学式: C₁₆H₁₇NO₂
• 分子量: 255.316
• InChiKey: JKZIAWXESLEONX-UHFFFAOYSA-N

物化性质

• 沸点：
  473.0±28.0 °C(Predicted)
• 密度：
  1.171±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(Trimethylacetamido)-2-naphthaldehyde 在 盐酸 、 三苯基膦 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  萘熔合的偶氮烯-炔类化合物中的缩水合物与周环反应性：苯并噻吩啉和苯并异吲唑类化合物的合成

  摘要：

  萘稠合的偶氮烯炔化合物的环化反应在计算和实验上都得到了探索。计算表明，与基于苯的系统相比，萘向偶氮-炔-炔骨架的融合不会显着改变过渡态能量。然而，由于形成具有更高芳香性的芳烃，以一定角度融合萘会降低能量中间体。实验上，角体系的环化不仅产生了预期的单体苯并肉桂啉和苯并异吲唑，而且还产生了几种二聚结构，包括在轻酸和/或痕量酸存在下易于异构化的二聚结构。

  DOI：

  10.1002/chem.201002936
• 作为产物：
  描述：

  2-羟基-3-萘甲酸 在 manganese(IV) oxide 、 ammonium hydroxide 、 lithium aluminium tetrahydride 、 硫酸 、 三乙胺 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 63.0h， 生成 3-(Trimethylacetamido)-2-naphthaldehyde
  参考文献：
  名称：

  Synthesis and Properties of Ligands Based on Benzo[g]quinoline

  摘要：

  The preparation of 3-amino-2-naphthaldehyde is described. Ammonolysis of 3-hydroxy-8-naphthoic acid affords the corresponding amino acid which can be esterified and then reduced with LAH. Protection of the amino group, MnO2 oxidation of the primary alcohol to an aldehyde, and deprotection gave the amino aldehyde which is an excellent Friedlander synthon for benzo[g]quinolines. Dimethylene-bridged analogues of 2,2'-bipyridine and 2,2';6,2''-terpyridine were prepared as well as orthocyclophanes derived from tetracyclo[6.3.0.0(4,11).0(5,9)]undecane-2,7-dione (TCU-2,7-dione). The absorption and emission spectra of these species are consistent with the parent benzo[g]quinoline where bathochromic shifts result from increased delocalization. The TCU derivative evidences exciplex formation so that its benzo[g]quinoline emission is almost completely quenched and an exciplex emission appears at 525 nm. Electrochemical analysis indicates that both reduction and UV absorption involve the same pi(*) orbital.

  DOI：

  10.1021/jo00083a024

文献信息

• Synthesis and Properties of Ligands Based on Benzo[g]quinoline
  作者：Emmanuelle Taffarel、Sarah Chirayil、Randolph P. Thummel

  DOI：10.1021/jo00083a024

  日期：1994.2

  The preparation of 3-amino-2-naphthaldehyde is described. Ammonolysis of 3-hydroxy-8-naphthoic acid affords the corresponding amino acid which can be esterified and then reduced with LAH. Protection of the amino group, MnO2 oxidation of the primary alcohol to an aldehyde, and deprotection gave the amino aldehyde which is an excellent Friedlander synthon for benzo[g]quinolines. Dimethylene-bridged analogues of 2,2'-bipyridine and 2,2';6,2''-terpyridine were prepared as well as orthocyclophanes derived from tetracyclo[6.3.0.0(4,11).0(5,9)]undecane-2,7-dione (TCU-2,7-dione). The absorption and emission spectra of these species are consistent with the parent benzo[g]quinoline where bathochromic shifts result from increased delocalization. The TCU derivative evidences exciplex formation so that its benzo[g]quinoline emission is almost completely quenched and an exciplex emission appears at 525 nm. Electrochemical analysis indicates that both reduction and UV absorption involve the same pi(*) orbital.
• Coarctate versus Pericyclic Reactivity in Naphthalene-Fused Azo-Ene-Ynes: Synthesis of Benzocinnolines and Benzoisoindazoles
  作者：Sean P. McClintock、Lev N. Zakharov、Rainer Herges、Michael M. Haley

  DOI：10.1002/chem.201002936

  日期：2011.6.6

  The cyclization reactions of naphthalene‐fused azo–ene–yne compounds are explored both computationally and experimentally. Calculations reveal that naphtho‐fusion to an azo–ene–yne scaffold does not significantly alter the transition state energies compared to the benzene‐based systems; however, fusing the naphthalene in an angular fashion leads to lower energy intermediates due to the creation of

  萘稠合的偶氮烯炔化合物的环化反应在计算和实验上都得到了探索。计算表明，与基于苯的系统相比，萘向偶氮-炔-炔骨架的融合不会显着改变过渡态能量。然而，由于形成具有更高芳香性的芳烃，以一定角度融合萘会降低能量中间体。实验上，角体系的环化不仅产生了预期的单体苯并肉桂啉和苯并异吲唑，而且还产生了几种二聚结构，包括在轻酸和/或痕量酸存在下易于异构化的二聚结构。