5-Chloro-13-methyl-1,9-diazatetracyclo[7.7.1.02,7.010,15]heptadeca-2(7),3,5,10(15),11,13-hexaene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 5-Chloro-13-methyl-1,9-diazatetracyclo[7.7.1.02,7.010,15]heptadeca-2(7),3,5,10(15),11,13-hexaene
• 英文别名: 5-chloro-13-methyl-1,9-diazatetracyclo[7.7.1.02,7.010,15]heptadeca-2(7),3,5,10(15),11,13-hexaene
• 化学式: C₁₆H₁₅ClN₂
• 分子量: 270.762
• InChiKey: IHVBBUKUFOWZNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-Chloro-13-methyl-1,9-diazatetracyclo[7.7.1.02,7.010,15]heptadeca-2(7),3,5,10(15),11,13-hexaene 在 2-双环己基膦-2',6'-二甲氧基联苯 、 palladium diacetate 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 3.0h， 生成 ethyl 3-methyl-2-((11R)-8-methyl-6,12-dihydro-5,11-methanodibenzo[b,f ][1,5]diazocin-2-yl)benzoate
  参考文献：
  名称：

  Unraveling the Role of Alkyl F on CH−π Interactions and Uncovering the Tipping Point for Fluorophobicity

  摘要：

  Although fluorine often plays an influential role in molecular recognition, little is known about the effect of aliphatic fluorine on the CH-pi interaction in solution. A series of molecular balances were synthesized that contain fluorinated and nonfluorinated alkyl groups. Our findings indicate that fluorine's polarizing ability does enhance CH-7r binding and depends on molecular orientation. Surprisingly, when the terminal end of the alkyl group is completely fluorinated, the balance tips toward fluorophobicity and assumes an unusual constrained conformation.

  DOI：

  10.1021/acs.joc.5b01072
• 作为产物：
  描述：

  聚合甲醛 、 4-Chloro-2-[(4-methylanilino)methyl]aniline 以 四氢呋喃 为溶剂， 以91%的产率得到5-Chloro-13-methyl-1,9-diazatetracyclo[7.7.1.02,7.010,15]heptadeca-2(7),3,5,10(15),11,13-hexaene
  参考文献：
  名称：

  Unraveling the Role of Alkyl F on CH−π Interactions and Uncovering the Tipping Point for Fluorophobicity

  摘要：

  Although fluorine often plays an influential role in molecular recognition, little is known about the effect of aliphatic fluorine on the CH-pi interaction in solution. A series of molecular balances were synthesized that contain fluorinated and nonfluorinated alkyl groups. Our findings indicate that fluorine's polarizing ability does enhance CH-7r binding and depends on molecular orientation. Surprisingly, when the terminal end of the alkyl group is completely fluorinated, the balance tips toward fluorophobicity and assumes an unusual constrained conformation.

  DOI：

  10.1021/acs.joc.5b01072

文献信息

• Improved synthesis of symmetrical and unsymmetrical 5,11-methanodibenzo[b,f][1,5]diazocines. Readily available nanoscale structural units
  作者：Thomas H. Webb、Craig S. Wilcox

  DOI：10.1021/jo00288a067

  日期：1990.1
• Unraveling the Role of Alkyl F on CH−π Interactions and Uncovering the Tipping Point for Fluorophobicity
  作者：Mark R. Ams、Michael Fields、Timothy Grabnic、Benjamin G. Janesko、Matthias Zeller、Rose Sheridan、Amanda Shay

  DOI：10.1021/acs.joc.5b01072

  日期：2015.8.7

  Although fluorine often plays an influential role in molecular recognition, little is known about the effect of aliphatic fluorine on the CH-pi interaction in solution. A series of molecular balances were synthesized that contain fluorinated and nonfluorinated alkyl groups. Our findings indicate that fluorine's polarizing ability does enhance CH-7r binding and depends on molecular orientation. Surprisingly, when the terminal end of the alkyl group is completely fluorinated, the balance tips toward fluorophobicity and assumes an unusual constrained conformation.