N,N-dibutyl-1-adamantanecarboxamide | 116415-18-0

• 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: N,N-dibutyl-1-adamantanecarboxamide
• 英文别名: N,N-dibutyladamantane-1-carboxamide；N-(adamantylcarbonyl)dibutylamine
• CAS: 116415-18-0
• 化学式: C₁₉H₃₃NO
• 分子量: 291.477
• InChiKey: LFBNVDJZDSUXPD-UHFFFAOYSA-N

物化性质

• 沸点：
  405.5±12.0 °C(Predicted)
• 密度：
  1.011±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N,N-dibutyl-1-adamantanecarboxamide 在 diborane(6) 作用下， 以 四氢呋喃 为溶剂， 以82%的产率得到Adamantan-1-ylmethyl-dibutyl-amine
  参考文献：
  名称：

  Amines That Transport Protons across Bilayer Membranes:  Synthesis, Lysosomal Neutralization, and Two-Phase pK_a Values by NMR

  摘要：

  It is desirable to be able to control the pH of lysosomes. A collection of lipophilic, nitrogenous bases, designed to act as membrane-active, catalytic proton transfer agents, were prepared and their effective pK(a)s measured in a vigorously stirred, two-phase system. One phase was a phosphate buffer whose pH was varied over the range ca, 1-11. The other was an immiscible, deuterated organic solvent in which the compounds preferentially resided even when protonated. When chemical shift changes versus the pH of the buffer were plotted, clear pK(a) curves were generated that are relevant to transmembrane proton transfer behavior. The two-phase pK(a)s increased with increasing counterion lipophilicity and with increasing organic solvent polarity, The compounds were also tested for their ability to neutralize the acidity of lysosomes, a model for other acidic vesicles involved in drug sorting. The most successful of these, imidazole 6a, has > 100 times the neutralizing power of ammonia, a standard lysosomotropic amine, causing a 1.7 unit rise in lysosomal pH of RAW cells at 0.1 mM, compared to a 0.2 and 1.4 unit rise for ammonium chloride at 0.1 and 10 mM, respectively.

  DOI：

  10.1021/jo960367f
• 作为产物：
  描述：

  金刚烷酰氯 在 palladium(II) bromide 三正丁胺 作用下， 以18%的产率得到N,N-dibutyl-1-adamantanecarboxamide
  参考文献：
  名称：

  桥头酰氯对钯催化的活化烯烃的酰化作用

  摘要：

  在催化量的钯和1当量的叔胺的存在下，桥头酰氯1a和1b与活化的烯烃2反应。反应在末端碳原子上进行区域选择性和立体选择性，以产生具有E-构型的酰化烯烃3。

  DOI：

  10.1016/s0040-4039(01)81080-7

文献信息

• Mild and Low-Pressure<i>fac</i>-Ir(ppy)₃-Mediated Radical Aminocarbonylation of Unactivated Alkyl Iodides through Visible-Light Photoredox Catalysis
  作者：Shiao Y. Chow、Marc Y. Stevens、Linda Åkerbladh、Sara Bergman、Luke R. Odell

  DOI：10.1002/chem.201601694

  日期：2016.6.27

  unactivated alkyl iodides employing a fac‐Ir(ppy)3‐catalyzed radical aminocarbonylation protocol has been developed. Using a two‐chambered system, alkyl iodides, fac‐Ir(ppy)3, amines, reductants, and CO gas (released ex situ from Mo(CO)6), were combined and subjected to an initial radical reductive dehalogenation generating alkyl radicals, and a subsequent aminocarbonylation with amines affording a

  已经开发出一种新颖，温和且简便的方法，可以通过未活化的烷基碘使用fac- Ir（ppy）3催化的自由基氨基羰基化方法制备烷基酰胺。使用两腔系统，将烷基碘，fac- Ir（ppy）3，胺，还原剂和CO气体（从Mo（CO）6异位释放）合并，并进行初始自由基还原性脱卤，生成烷基自由基，然后用胺进行氨基羰基化，以中等到极好的收率提供了广泛的烷基酰胺。
• HORI, KIMIHIKO;ANDO, MASATOMO;TAKAISHI, NAOTAKE;INAMOTO, YOSHIAKI, TETRAHEDORON LETT., 28,(1987) N 47, 5883-5886
  作者：HORI, KIMIHIKO、ANDO, MASATOMO、TAKAISHI, NAOTAKE、INAMOTO, YOSHIAKI

  DOI：——

  日期：——
• Palladium-catalyzed acylation of activated alkenes with bridgehead acid chlorides
  作者：Kimihiko Hori、Masatomo Ando、Naotake Takaishi、Yoshiaki Inamoto

  DOI：10.1016/s0040-4039(01)81080-7

  日期：1987.1

  Bridgehead acid chlorides 1a and 1b react with activated alkenes 2 in the presence of a catalytic amount of palladium and 1 equiv of a tertiary amine. The reaction proceeds regio- and stereoselectively at the terminal carbon atoms to yield acylated alkenes 3 with E-configuration.

  在催化量的钯和1当量的叔胺的存在下，桥头酰氯1a和1b与活化的烯烃2反应。反应在末端碳原子上进行区域选择性和立体选择性，以产生具有E-构型的酰化烯烃3。
• Amines That Transport Protons across Bilayer Membranes:  Synthesis, Lysosomal Neutralization, and Two-Phase p<i>K</i>_a Values by NMR
  作者：Gene M. Dubowchik、Linda Padilla、Kurt Edinger、Raymond A. Firestone

  DOI：10.1021/jo960367f

  日期：1996.1.1

  It is desirable to be able to control the pH of lysosomes. A collection of lipophilic, nitrogenous bases, designed to act as membrane-active, catalytic proton transfer agents, were prepared and their effective pK(a)s measured in a vigorously stirred, two-phase system. One phase was a phosphate buffer whose pH was varied over the range ca, 1-11. The other was an immiscible, deuterated organic solvent in which the compounds preferentially resided even when protonated. When chemical shift changes versus the pH of the buffer were plotted, clear pK(a) curves were generated that are relevant to transmembrane proton transfer behavior. The two-phase pK(a)s increased with increasing counterion lipophilicity and with increasing organic solvent polarity, The compounds were also tested for their ability to neutralize the acidity of lysosomes, a model for other acidic vesicles involved in drug sorting. The most successful of these, imidazole 6a, has > 100 times the neutralizing power of ammonia, a standard lysosomotropic amine, causing a 1.7 unit rise in lysosomal pH of RAW cells at 0.1 mM, compared to a 0.2 and 1.4 unit rise for ammonium chloride at 0.1 and 10 mM, respectively.