3-(1-Adamantylcarbamoyl)bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-(1-Adamantylcarbamoyl)bicyclo[2.2.1]hept-5-ene-2-carboxylic acid
• 英文别名: 3-(1-adamantylcarbamoyl)bicyclo[2.2.1]hept-5-ene-2-carboxylic acid
• 化学式: C₁₉H₂₅NO₃
• 分子量: 315.412
• InChiKey: QOVVJJKOVRXEPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(1-Adamantylcarbamoyl)bicyclo[2.2.1]hept-5-ene-2-carboxylic acid 在 sodium acetate 、 乙酸酐 作用下， 反应 2.0h， 以85%的产率得到N-(1-adamantyl)-exo-norbornene-5,6-dicarboximide
  参考文献：
  名称：

  Synthesis and Gas Transport Properties of New High Glass Transition Temperature Ring-Opened Polynorbornenes

  摘要：

  The synthesis and polymerization of the new monomers N-(1-adamantyl)-exo-norbornene-5,6-dicarboximide (AdNDI), N-cyclohexyl-exo-norbornene-5,6-dicarboximide (ChNDI), and N-phenyl-exonorbornene-5,6-dicarboximide (PhNDI) are reported. Copolymers of IV-(1-adamantyl)-exo-norbornene-5,6-dicarboximide/norbornene, with molar compositions 50/50, 70/30, and 30/70, were also obtained. The transport of hydrogen, oxygen, nitrogen, carbon monoxide, carbon dioxide, methane, ethylene, and ethane across membranes prepared from these homopolymers and copolymers was determined at 30 degreesC using permeation techniques. Diffusion coefficients correlate rather well with the diameter of diffusant molecules except in the case of carbon dioxide. The values of the permselectivity coefficient for different gases depend on the type of membranes. For example, the permselectivity of oxygen with respect to nitrogen, alpha(O-2/N-2), is ca. 5.50 for membranes prepared from N-(1-adamantyl)-exo-norbornene-5,6-dicarboximide/norbornene (50/50) copolymers, which compares favorably with the values reported for this parameter in membranes with imide groups located in the backbone. The values of alpha(H-2/C2H6) in membranes of poly(N-(1-adamantyl)-exo-norbornene-5,6-dicarboximide), poly(N-cyclohexyl-exo-norbornene-5,6-dicarboximide), and poly(N-phenyl-exo-norbornene-5,6-dicarboximide) are 183, 124, and 122, respectively, whereas the values of alpha(C2H4/C2H6) amount to 6.9, 7.6, and 6.4, respectively. For most membranes used in this study, diffusion rather than solubility is responsible for the discrimination of gas transport. However, solubility is mainly responsible for the high permselectivity of ethylene with respect to ethane displayed by the membranes.

  DOI：

  10.1021/ma011959p
• 作为产物：
  描述：

  环戊二烯 以 甲苯 为溶剂， 反应 1.0h， 生成 3-(1-Adamantylcarbamoyl)bicyclo[2.2.1]hept-5-ene-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and Gas Transport Properties of New High Glass Transition Temperature Ring-Opened Polynorbornenes

  摘要：

  The synthesis and polymerization of the new monomers N-(1-adamantyl)-exo-norbornene-5,6-dicarboximide (AdNDI), N-cyclohexyl-exo-norbornene-5,6-dicarboximide (ChNDI), and N-phenyl-exonorbornene-5,6-dicarboximide (PhNDI) are reported. Copolymers of IV-(1-adamantyl)-exo-norbornene-5,6-dicarboximide/norbornene, with molar compositions 50/50, 70/30, and 30/70, were also obtained. The transport of hydrogen, oxygen, nitrogen, carbon monoxide, carbon dioxide, methane, ethylene, and ethane across membranes prepared from these homopolymers and copolymers was determined at 30 degreesC using permeation techniques. Diffusion coefficients correlate rather well with the diameter of diffusant molecules except in the case of carbon dioxide. The values of the permselectivity coefficient for different gases depend on the type of membranes. For example, the permselectivity of oxygen with respect to nitrogen, alpha(O-2/N-2), is ca. 5.50 for membranes prepared from N-(1-adamantyl)-exo-norbornene-5,6-dicarboximide/norbornene (50/50) copolymers, which compares favorably with the values reported for this parameter in membranes with imide groups located in the backbone. The values of alpha(H-2/C2H6) in membranes of poly(N-(1-adamantyl)-exo-norbornene-5,6-dicarboximide), poly(N-cyclohexyl-exo-norbornene-5,6-dicarboximide), and poly(N-phenyl-exo-norbornene-5,6-dicarboximide) are 183, 124, and 122, respectively, whereas the values of alpha(C2H4/C2H6) amount to 6.9, 7.6, and 6.4, respectively. For most membranes used in this study, diffusion rather than solubility is responsible for the discrimination of gas transport. However, solubility is mainly responsible for the high permselectivity of ethylene with respect to ethane displayed by the membranes.

  DOI：

  10.1021/ma011959p

文献信息

• Synthesis and Gas Transport Properties of New High Glass Transition Temperature Ring-Opened Polynorbornenes
  作者：Armando Pineda Contreras、Mikhail A. Tlenkopatchev、Maria del Mar López-González、Evaristo Riande

  DOI：10.1021/ma011959p

  日期：2002.6.1

  The synthesis and polymerization of the new monomers N-(1-adamantyl)-exo-norbornene-5,6-dicarboximide (AdNDI), N-cyclohexyl-exo-norbornene-5,6-dicarboximide (ChNDI), and N-phenyl-exonorbornene-5,6-dicarboximide (PhNDI) are reported. Copolymers of IV-(1-adamantyl)-exo-norbornene-5,6-dicarboximide/norbornene, with molar compositions 50/50, 70/30, and 30/70, were also obtained. The transport of hydrogen, oxygen, nitrogen, carbon monoxide, carbon dioxide, methane, ethylene, and ethane across membranes prepared from these homopolymers and copolymers was determined at 30 degreesC using permeation techniques. Diffusion coefficients correlate rather well with the diameter of diffusant molecules except in the case of carbon dioxide. The values of the permselectivity coefficient for different gases depend on the type of membranes. For example, the permselectivity of oxygen with respect to nitrogen, alpha(O-2/N-2), is ca. 5.50 for membranes prepared from N-(1-adamantyl)-exo-norbornene-5,6-dicarboximide/norbornene (50/50) copolymers, which compares favorably with the values reported for this parameter in membranes with imide groups located in the backbone. The values of alpha(H-2/C2H6) in membranes of poly(N-(1-adamantyl)-exo-norbornene-5,6-dicarboximide), poly(N-cyclohexyl-exo-norbornene-5,6-dicarboximide), and poly(N-phenyl-exo-norbornene-5,6-dicarboximide) are 183, 124, and 122, respectively, whereas the values of alpha(C2H4/C2H6) amount to 6.9, 7.6, and 6.4, respectively. For most membranes used in this study, diffusion rather than solubility is responsible for the discrimination of gas transport. However, solubility is mainly responsible for the high permselectivity of ethylene with respect to ethane displayed by the membranes.