2-(cyanomethyl)-1,4-dimethoxynaphthalene | 79971-25-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(cyanomethyl)-1,4-dimethoxynaphthalene
• 英文别名: (1,4-dimethoxynaphth-2-yl)acetonitrile；1,4-dimethoxy-2-naphthylacetonitrile；1,4-Dimethoxy-2-naphthaleneacetonitrile；2-(1,4-dimethoxynaphthalen-2-yl)acetonitrile
• CAS: 79971-25-8
• 化学式: C₁₄H₁₃NO₂
• 分子量: 227.263
• InChiKey: JDWUPSGTRWWSNK-UHFFFAOYSA-N

物化性质

• 熔点：
  111.5-113 °C(Solv: methanol (67-56-1))
• 沸点：
  407.7±30.0 °C(Predicted)
• 密度：
  1.149±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  42.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(cyanomethyl)-1,4-dimethoxynaphthalene 在 氢氧化钾 、 magnesium 作用下， 以 甲醇 、 乙醚 、 水 为溶剂， 反应 42.42h， 生成 1,4-dimethoxy-2-<2,2-dianisyl)vinyl>naphthalene
  参考文献：
  名称：

  Condensation of naphthoquinones with polar ethylenes. A reexamination

  摘要：

  DOI：

  10.1021/jo00342a045
• 作为产物：
  描述：

  1,4-二甲氧基萘-2-甲醛 在 sodium tetrahydroborate 、 三溴化磷 作用下， 以 甲醇 、 四氯化碳 、 乙醇 为溶剂， 反应 3.5h， 生成 2-(cyanomethyl)-1,4-dimethoxynaphthalene
  参考文献：
  名称：

  两种萘醌类抗生素精神红蛋白和五角糖素的简单合成

  摘要：

  摘要 以取代-2-萘乙酸的氯甲基化反应为关键步骤，合成了1H-萘并[2,3-c]吡喃-5,10-二酮衍生物。这种方法的效用在双吡喃萘醌类抗生素精神红素 (1) 和五角糖素 (2) 的合成中得到了证明。

  DOI：

  10.1081/scc-120015812

文献信息

• Investigation of the Reaction of 2-Bromo-1,4-dimethoxynaphthalene and 9-Bromophenanthrene with Nitriles Under Aryne-Forming Conditions
  作者：Marcus Hansen、Subhash P. Khanapure、Michael Fry、Dan Swartling、Edward R. Biehl

  DOI：10.1055/s-1994-25613

  日期：——

  The reaction of 2-bromo-1,4-dimethoxynaphthalene (1) and 9-bromophenanthrene (3) with nitriles 2 under base-mediated, aryne-forming conditions gives product distributions which depend upon the nature of the bromoarene, nitrile, base, and the reaction medium. Thus, treatment of 1 with arylacetonitriles 2a-d in the presence of LDA in THF or sodium amide in liquid ammonia supplies α-aryl-1,4-dimethoxy-2-naphthylacetonitriles 4a-d, presumably by the aryne arylation mechanism. In contrast, the reaction of 9-bromo-phenanthrene (3) and arylacetonitriles 2b-e with LDA in THF yields 10-arylmethyl-9- phenanthrenecarbonitriles 6b-e, most likely by the tandem addition-rearrangement pathway. When 3 reacts with 2a-c in the presence of sodium amide and liquid ammonia, α-aryl-9-phenanthrylacetonitriles 5a-c, rather than the rearranged nitriles 6a-c, are obtained. Both 1 and 3 react with alkylnitriles 2f-i and LDA-THF, sodium amide-liquid ammonia, or Caubere's sodamide base to afford aryne arylated nitriles (4f-i and 5f-i, respectively). An explanation in terms of the influence of reactants and solvent on the competition between the aryne arylation and tandem addition-rearrangement pathways is presented.

  2-溴-1,4-二甲氧基萘（1）和9-溴菲（3）与腈2在碱介导、芳炔形成条件下反应，产物的分布取决于溴芳烃、腈、碱和反应介质的性质。因此，在LDA存在下，1与芳基乙腈2a-d在四氢呋喃中或与钠胺在液态氨中反应，推测通过芳炔芳基化机制生成α-芳基-1,4-二甲氧基-2-萘基乙腈4a-d。相反，9-溴菲（3）与芳基乙腈2b-e在LDA存在下的四氢呋喃中反应，最可能通过串联加成-重排途径生成10-芳甲基-9-菲碳腈6b-e。当3与2a-c在钠胺和液态氨存在下反应时，得到的是α-芳基-9-菲乙腈5a-c，而不是重排的腈6a-c。1和3均与烷基腈2f-i以及LDA-THF、钠胺-液态氨或Caubere的钠胺碱反应，生成芳炔芳基化腈（分别为4f-i和5f-i）。本文提出了关于反应物和溶剂对芳炔芳基化和串联加成-重排途径竞争影响的解释。
• The Synthesis of Radermachol
  作者：Balawant S. Joshi、Quingping Jiang、Taikyun Rho、S. William Pelletier

  DOI：10.1021/jo00105a046

  日期：1994.12

  Five different approaches to the preparation of 6,7-benzo-3,4-(1,4-dimethoxy-2,3-naphtho)-1,5-dioxosuberane (3), an intermediate needed for the synthesis of radermachol (1), the red pigment from the roots of Radermachera xylocarpa, are described. The synthesis of radermachol (1) has been accomplished from 1,4-nephthoquinone in 14 steps.
• Synthesis of N-substituted 1,2,3,4-tetrahydrobenz[g]isoquinoline-5,10-diones
  作者：Jan Jacobs、Jurgen Deblander、Bart Kesteleyn、Kourosch Abbaspour Tehrani、Norbert De Kimpe

  DOI：10.1016/j.tet.2008.03.014

  日期：2008.5

  The synthesis of 1,2,3,4-tetrahydrobenz[g]isoquinoline-5,10-dione hydrochlorides is reported starting from 1,4-dihydrobenz[g]isoquinoline-3(2H)-ones or ethyl (3-aminomethyl-1,4-dimethoxynaphth-2-yl)acetates. A third strategy relies on the synthesis of the title compounds via an N-protected 2-(3-bromomethyl-1,4-dimethoxynaphth-2-yl)ethylamine. The synthesized 1,2,3,4-tetrahydro-benz[g]isoquinoline-5,10-diones are a new class of quinones, which have not been reported yet. (C) 2008 Published by Elsevier Ltd.
• GATES, M., J. ORG. CHEM., 1982, 47, N 3, 578-582
  作者：GATES, M.

  DOI：——

  日期：——
• Condensation of naphthoquinones with polar ethylenes. A reexamination
  作者：Marshall Gates

  DOI：10.1021/jo00342a045

  日期：1982.1