1-(4-Methoxy-benzyl)-1,2-dihydro-naphthalene-1,4-dicarbonitrile | 95065-55-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(4-Methoxy-benzyl)-1,2-dihydro-naphthalene-1,4-dicarbonitrile
• 英文别名: 1-[(4-methoxyphenyl)methyl]-2H-naphthalene-1,4-dicarbonitrile
• CAS: 95065-55-7
• 化学式: C₂₀H₁₆N₂O
• 分子量: 300.36
• InChiKey: ORSMMOCABGQVBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.01
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  56.81
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-(4-Methoxy-benzyl)-1,2-dihydro-naphthalene-1,4-dicarbonitrile 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以80%的产率得到1-cyano-4-(4-methoxyphenylmethyl)naphthalene
  参考文献：
  名称：

  SET Photochemical Reactions between 1,4-Naphthalenedicarbonitrile and Benzylic Donors. Medium Effects

  摘要：

  The electron transfer induced photochemical reactions of 1,4-naphthalenedicarbonitrile (NDN) with toluene (1a), diphenylmethane (1b), p-methoxytoluene (1c), and benzyltrimethylsilane (1d) in MeOH-MeCN and 0.1 M KOH-MeOH-MeCN were examined. The results were compared with those of reactions occurring in neat MeCN. Under the former conditions, the cation radical derived from 1a undergoes deprotonation after diffusion from (rather than within) the geminate ion pair (as in MeCN). The formed benzyl radical abstracts a hydrogen from MeOH leading to hydroxymethylation of NDN competitively with its benzylation. Under basic conditions MeO(-) adds to 1a(+.) yielding 1c. The reaction of 1b in MeOH-MeCN and 0.1 M KOH-MeOH-MeCN is similar to that of 1a. However, in the reaction of 1c under these conditions, the arene cation radical undergoes deprotonation out of cage. Finally, desilylation of the cation radical from 1d is a fast process occurring from the geminate pair in all the media explored.

  DOI：

  10.1021/jo00083a025
• 作为产物：
  描述：

  cis-2-(1,1-Diphenylmethyl)-1,2-dihydro-1,4-naphthalenedicarbonitrile 在 氢氧化钾 作用下， 以 甲醇 、 乙醇 、 乙腈 为溶剂， 反应 11.0h， 生成 1-(4-Methoxy-benzyl)-1,2-dihydro-naphthalene-1,4-dicarbonitrile
  参考文献：
  名称：

  SET Photochemical Reactions between 1,4-Naphthalenedicarbonitrile and Benzylic Donors. Medium Effects

  摘要：

  The electron transfer induced photochemical reactions of 1,4-naphthalenedicarbonitrile (NDN) with toluene (1a), diphenylmethane (1b), p-methoxytoluene (1c), and benzyltrimethylsilane (1d) in MeOH-MeCN and 0.1 M KOH-MeOH-MeCN were examined. The results were compared with those of reactions occurring in neat MeCN. Under the former conditions, the cation radical derived from 1a undergoes deprotonation after diffusion from (rather than within) the geminate ion pair (as in MeCN). The formed benzyl radical abstracts a hydrogen from MeOH leading to hydroxymethylation of NDN competitively with its benzylation. Under basic conditions MeO(-) adds to 1a(+.) yielding 1c. The reaction of 1b in MeOH-MeCN and 0.1 M KOH-MeOH-MeCN is similar to that of 1a. However, in the reaction of 1c under these conditions, the arene cation radical undergoes deprotonation out of cage. Finally, desilylation of the cation radical from 1d is a fast process occurring from the geminate pair in all the media explored.

  DOI：

  10.1021/jo00083a025

文献信息

• Albini, Angelo; Fasani, Elisa; Montessoro, Ezio, Zeitschrift fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1984, vol. 39, # 10, p. 1409 - 1415
  作者：Albini, Angelo、Fasani, Elisa、Montessoro, Ezio

  DOI：——

  日期：——