8-methoxy-1-naphthaldehyde | 35689-27-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 8-methoxy-1-naphthaldehyde
• 英文别名: 8-Methoxynaphthalene-1-carbaldehyde
• CAS: 35689-27-1
• 化学式: C₁₂H₁₀O₂
• 分子量: 186.21
• InChiKey: YFLPAVAWVYNUBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8-methoxy-1-naphthaldehyde 在 三氯化铝 作用下， 生成 8-羟基-1-萘甲醛
  参考文献：
  名称：

  锂化反应的合成应用-VII：线性和有角萘呋喃和苯并香豆素的新合成

  摘要：

  使用锂化反应，已经合成了四种甲氧基和羟基萘醛。其中三个已被转化为相应的萘呋喃和苯并香豆素。

  DOI：

  10.1016/0040-4020(75)80118-9
• 作为产物：
  描述：

  2H-萘并[1,8-bc]呋喃-2-酮 在 氢氧化钾 、 lithium tri-t-butoxyaluminum hydride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 20.0h， 生成 8-methoxy-1-naphthaldehyde
  参考文献：
  名称：

  Selective Synthesis of meso-Naphthylporphyrins

  摘要：

  A series of novel meso-(8-substituted naphth-1-yl)porphyrins has been synthesized creating derivatives with a tight recognition environment above the porphyrin plane. The selective synthesis of single atropisomers is discussed. Condensation of bisnaphthaldehyde 12 with phenyldipyrromethane unexpectedly led to selective synthesis of the alpha,alpha-5,10-bridged isomer 14. A mechanism is proposed for this unusual scrambling, and alternative syntheses of alpha,alpha-5,15-bisnaphthylporphyrins are described. Synthesis of 5,15-analogues can be achieved by employing (pentafluorophenyl)dipyrromethane or via presynthesis of a bis(dipyrromethane) derivative 22 (from bisnaphthaldehyde 12) and subsequent condensation with benzaldehyde.

  DOI：

  10.1021/jo0260488

文献信息

• Biocatalytic dynamic kinetic reductive resolution with ketoreductase from <i>Klebsiella pneumoniae</i>: the asymmetric synthesis of functionalized tetrahydropyrans
  作者：Rasmita Barik、Joydev Halder、Samik Nanda

  DOI：10.1039/c9ob01681c

  日期：——

  substituted-β-ketoesters to the corresponding β-hydroxy esters with excellent yields and stereoselectivities (ee and de >99 %). The reactions described herein followed a biocatalytic dynamic kinetic reductive resolution (DKRR) pathway, which is reported for the first time with such substrates. It was found that the enzyme system can accept substituted mono-aryl rings with different electronic natures

  来自肺炎克雷伯菌的生长细胞的酮还原酶（NBRC 3319）是一种高效的试剂，可将外消旋的α-苄基/肉桂基取代的β-酮酸酯转化为相应的β-羟基酯，并具有出色的收率和立体选择性（ee和de> 99％）。本文所述的反应遵循生物催化动态动力学还原拆分（DKRR）途径，首次报道了这种底物。发现该酶系统可以接受具有不同电子性质的取代的单芳基环。另外，它还在母体β-酮酸酯的α-位接受取代的萘基环和杂芳基环。然后将合成的对映体纯β-羟基酯合成为有价值的四氢吡喃结构单元。
• Novel Asymmetric Formylation of Aromatic Compounds: Enantioselective Synthesis of Formyl 7,8-Dipropyltetrathia[7]helicenes
  作者：Julien Doulcet、G. Richard Stephenson

  DOI：10.1002/chem.201501627

  日期：2015.9.14

  Asymmetric formylation of aromatic compounds is virtually unexplored. We report the synthesis and evaluation of a library including 20 new chiral formamides in the kinetic resolution of 7,8‐dipropyltetrathia[7]helicene, affording the corresponding formyl‐ or diformylhelicenes in up to 73 % ee, making enantiopure compounds available by recrystallisation. With the N,N‐disubstituted formamides used in

  芳香族化合物的不对称甲酰化实际上是未开发的。我们报告了在20,8-二丙基四硫杂[7]螺旋动力学拆分中包括20种新的手性甲酰胺的文库的合成和评估，提供了高达73％ee的相应的甲酰基-或二甲酰基螺旋烯，通过重结晶可得到对映纯化合物。通过本研究中使用的N，N-二取代甲酰胺，R 1 = i Pr，R 2 = Me，R 3 = H，R 4 = 1-萘基或其等价基团达到了最佳的对映选择性。
• Synthetic application of lithiation reactions—VII
  作者：N.S. Narasimhan、R.S. Mali

  DOI：10.1016/0040-4020(75)80118-9

  日期：——

  Using lithiation reaction, four methoxy and hydroxynaphthaldehydes have been synthesised. Three of these have been converted into the corresponding naphthofurans and benzocoumarins.

  使用锂化反应，已经合成了四种甲氧基和羟基萘醛。其中三个已被转化为相应的萘呋喃和苯并香豆素。
• Regioselectivity in the reactions of methoxydehydrobenzenes with furans. Part 1. Reactions of 3-methoxydehydrobenzene and 3-(methoxycarbonyl)-dehydrobenzene with 2-substituted furans
  作者：Robin G. F. Giles、Melvyn V. Sargent、Hercules Sianipar

  DOI：10.1039/p19910001571

  日期：——

  obtained for the reaction of 3-methoxydehydrobenzene, generated from 2-amino-6-methoxybenzoic acid by aprotic diazotization, or from 2-bromo-3-methoxyphenyl toluene-p-sulphonate by treatment with butyllithium, and for the reaction of 3-(methoxycarbonyl)dehydrobenzene, generated from 2-amino-6-(methoxycarbonyl) benzoic acid by aprotic diazotization, with seven 2-substituted furans are recorded. These

  由2-氨基-6-甲氧基苯甲酸通过非质子重氮化而生成的3-甲氧基脱氢苯的反应，或由2-溴-3-甲氧基苯基甲苯-对磺酸酯经丁基锂的处理而生成的3-甲氧基脱氢苯的反应的环加合物的异构体比，以及记录了由2-氨基-6-（甲氧羰基）苯甲酸经质子重氮化而生成的3-（甲氧羰基）脱氢苯与七种2-取代的呋喃的反应。将根据异步，协调一致的双自由基反应途径来讨论这些结果。
• Attractive and repulsive effects in the interactions between electron-rich and electron-deficient groups in peri-substituted naphthalenes
  作者：Jane O’Leary、Paul C. Bell、John D. Wallis、W. Bernd Schweizer

  DOI：10.1039/b008226k

  日期：——

  accord with the different nucleophilicities of the two groups. These separations are a balance between a steric effect and a covalent interaction, and from a comparison of the Me2N⋯C and MeO⋯C distances for a given functional group it is proposed that the Me2N⋯C interaction has an attractive component if the Me2N⋯C separation is less than ∼(MeO⋯C + 0.15) Å, the latter factor arising from the greater size

  一系列周边取代的1,5 Me 2 N ⋯ C（sp 2）分离萘衍生物对含碳官能团的全空间电子吸引能力敏感，而相应的MeO ⋯ C（sp 2）分离对这两个基团的不同亲核性则相对不敏感。这些分离是空间效应和共价相互作用之间的平衡，并且通过比较给定官能团的Me 2 N ⋯ C和MeO ⋯ C距离，提出Me 2 N ⋯ C相互作用具有诱人的成分如果Me 2 N ⋯ C的分离度小于〜（MeO ⋯C + 0.15）Å，后者是由键合的较大尺寸引起的 氮原子。