2-(2,2-Dimethoxyethyl)-1-nitronaphthalene | 592478-91-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(2,2-Dimethoxyethyl)-1-nitronaphthalene
• CAS: 592478-91-6
• 化学式: C₁₄H₁₅NO₄
• 分子量: 261.277
• InChiKey: ALNPCZZPKHSREH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  64.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2,2-Dimethoxyethyl)-1-nitronaphthalene 在 三氟乙酸 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 8.0h， 生成 (S)-2-((R)-2-Hydroxy-1-phenyl-ethylamino)-3-(1-nitro-naphthalen-2-yl)-propionitrile
  参考文献：
  名称：

  Indolactam-V Is Involved in the CH/π Interaction with Pro-11 of the PKCδ C1B Domain:  Application for the Structural Optimization of the PKCδ Ligand

  摘要：

  The CH/pi interaction between the indole ring of indolactam-V (IL-V) and the hydrogen atom at position 4 of Pro-11 of the PKCdelta C1B domain was evaluated using the mutant peptide of the PKCdelta C1B domain, in which the CH/pi interaction was inhibited by substitution of the hydrogen atom with a fluorine atom. IL-V showed about a 10 times lower binding affinity to the mutant peptide compared to the wild-type peptide, suggesting that the CH/pi interaction could play a pivotal role in the binding of IL-V to the PKCdelta C1B domain. On the other hand, benzolactam-V8 (BL-V8), with the benzene ring instead of the indole ring of IL-V, might lack the CH/pi interaction. The low binding affinity of BL-V8 could be enhanced by the effective formation of the CH/pi interaction as exemplified by the synthesis of naphtholactam-V8 (NL-V8).

  DOI：

  10.1021/ja050447d
• 作为产物：
  描述：

  2-甲基-二硝基萘酚 在 camphor-10-sulfonic acid 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成 2-(2,2-Dimethoxyethyl)-1-nitronaphthalene
  参考文献：
  名称：

  Indolactam-V Is Involved in the CH/π Interaction with Pro-11 of the PKCδ C1B Domain:  Application for the Structural Optimization of the PKCδ Ligand

  摘要：

  The CH/pi interaction between the indole ring of indolactam-V (IL-V) and the hydrogen atom at position 4 of Pro-11 of the PKCdelta C1B domain was evaluated using the mutant peptide of the PKCdelta C1B domain, in which the CH/pi interaction was inhibited by substitution of the hydrogen atom with a fluorine atom. IL-V showed about a 10 times lower binding affinity to the mutant peptide compared to the wild-type peptide, suggesting that the CH/pi interaction could play a pivotal role in the binding of IL-V to the PKCdelta C1B domain. On the other hand, benzolactam-V8 (BL-V8), with the benzene ring instead of the indole ring of IL-V, might lack the CH/pi interaction. The low binding affinity of BL-V8 could be enhanced by the effective formation of the CH/pi interaction as exemplified by the synthesis of naphtholactam-V8 (NL-V8).

  DOI：

  10.1021/ja050447d

文献信息

• Synthesis of 3-methoxyquinolines via cyclization of 1-isocyano-2-(2-lithio-2-methoxyethenyl)benzenes
  作者：Kazuhiro Kobayashi、Keiichi Yoneda、Tatsuya Mizumoto、Hironobu Umakoshi、Osamu Morikawa、Hisatoshi Konishi

  DOI：10.1016/s0040-4039(03)01040-2

  日期：2003.6

  2-(2-Isocyanophenyl)acetaldehyde dimethyl acetals were treated with excess LDA to generate 1-isocyano-2-(2-lithio-2-methoxyethenyl)benzenes, which cyclized intramolecularly to afford 3-methoxyquinolines in good to excellent yields. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Indolactam-V Is Involved in the CH/π Interaction with Pro-11 of the PKCδ C1B Domain:  Application for the Structural Optimization of the PKCδ Ligand
  作者：Yu Nakagawa、Kazuhiro Irie、Ryo C. Yanagita、Hajime Ohigashi、Ken-ichiro Tsuda

  DOI：10.1021/ja050447d

  日期：2005.4.1

  The CH/pi interaction between the indole ring of indolactam-V (IL-V) and the hydrogen atom at position 4 of Pro-11 of the PKCdelta C1B domain was evaluated using the mutant peptide of the PKCdelta C1B domain, in which the CH/pi interaction was inhibited by substitution of the hydrogen atom with a fluorine atom. IL-V showed about a 10 times lower binding affinity to the mutant peptide compared to the wild-type peptide, suggesting that the CH/pi interaction could play a pivotal role in the binding of IL-V to the PKCdelta C1B domain. On the other hand, benzolactam-V8 (BL-V8), with the benzene ring instead of the indole ring of IL-V, might lack the CH/pi interaction. The low binding affinity of BL-V8 could be enhanced by the effective formation of the CH/pi interaction as exemplified by the synthesis of naphtholactam-V8 (NL-V8).