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2-butyl-3a,4,5,7,7a-hexahydro-1H-benzimidazole | 179249-26-4

中文名称
——
中文别名
——
英文名称
2-butyl-3a,4,5,7,7a-hexahydro-1H-benzimidazole
英文别名
2-butyl-3a,4,5,6,7,7a-hexahydro-1H-benzimidazole
2-butyl-3a,4,5,7,7a-hexahydro-1H-benzimidazole化学式
CAS
179249-26-4
化学式
C11H20N2
mdl
——
分子量
180.293
InChiKey
DTPPONSABJMVPW-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    1.9
  • 重原子数:
    13
  • 可旋转键数:
    3
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.91
  • 拓扑面积:
    24.4
  • 氢给体数:
    1
  • 氢受体数:
    1

反应信息

  • 作为反应物:
    描述:
    2-butyl-3a,4,5,7,7a-hexahydro-1H-benzimidazole草酰氯二甲基亚砜三乙胺 作用下, 以 二氯甲烷 为溶剂, 以82%的产率得到2-butyl-4,5,6,7-tetrahydro-1H-benzimidazole
    参考文献:
    名称:
    Amines That Transport Protons across Bilayer Membranes:  Synthesis, Lysosomal Neutralization, and Two-Phase pKa 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:
    参考文献:
    名称:
    Amines That Transport Protons across Bilayer Membranes:  Synthesis, Lysosomal Neutralization, and Two-Phase pKa 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
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文献信息

  • Amines That Transport Protons across Bilayer Membranes:  Synthesis, Lysosomal Neutralization, and Two-Phase p<i>K</i><sub>a</sub> 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.
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同类化合物

辛基羟乙基咪唑啉 辛基羟乙基咪唑啉 肉豆蔻基羟乙基咪唑啉 甲基-(1-甲基-吡咯烷-2-亚基)-胺 甲基(5-甲基-1,2-恶唑-3-基)氨基甲酸酯 油基胺乙基咪唑啉 氯代醋酸钠与4,5-二氢-十一烷基-1H-咪唑-1-乙醇和氢氧化钠的反应产物 月桂基羟乙基咪唑啉 恶唑-4-基氨基甲酸叔丁酯 异硬脂基羟乙基咪唑啉 异噁隆 异丙基亚氨基吡咯烷 噻唑-2,4-二胺 噁唑-4-胺 叔-丁基2-氨基-6,7-二氢吡唑并[1,5-A]吡嗪-5(4H)-甲酸基酯 十七碳-2-烯基-4,5-二氢-1H-咪唑-1-乙醇盐酸盐 偶氮引发剂VA-064 依凡达明 二氨基吡唑 乙基3-(乙基氨基)-5-甲基-1,2-恶唑-4-羧酸酯 alpha-(氯甲基)-2-异丙基-5-硝基-2H-咪唑-2-乙醇 alpha,4,4-三甲基-2-十一烷基-2-咪唑啉-1-乙醇 Z-2-(8-十七烯基)-4,5-二氢-1H-咪唑-1-乙醇 N-甲基-3-氨基吡唑 N-甲基-2-吡咯烷酮肟 N-甲基-1,2-噻唑-3-胺1,1-二氧化物 N-环己基-1,2-噻唑-3-胺1,1-二氧化物 N-叔-丁基-5-甲基-2H-吡唑-3-胺 N-乙基-N-(5-甲基-3-异恶唑基)-乙酰胺 N-乙基-1,2-噻唑-3-胺1,1-二氧化物 N-乙基-1,2,5-恶二唑-3,4-二胺 N-[2-[2-[(E)-十七碳-8-烯基]-4,5-二氢咪唑-1-基]乙基]乙烷-1,2-二胺 N-[2-[2-(13-二十一碳烯-1-基)-4,5-二氢-1H-咪唑-1-基]乙基]乙二胺 N-[2-(4,5-二氢-2-十九烷基-1H-咪唑-1-基)乙基]乙二胺 N-[2-(4,5-二氢-2-十一烷基-1H-咪唑-1-基)乙基]乙二胺 N-[(2Z)-哌嗪-2-亚基]-2,2,2-三氟乙酰肼 N-[(2-甲基苯基)氨基甲硫杂酰]-2-(4-羰基-2-苯基喹唑啉-3(4H)-基)-3-苯基丙酰胺 N-BOC-4-氨基噻唑 N-3-异恶唑氨基甲酸叔丁酯 N-(噻二唑-4-基)氨基甲酸乙酯 N-(5-叔丁基-1H-吡唑-3-基)氨基甲酸甲酯 N-(4,5-二甲基-3-异噁唑)氨基甲酸1,1-二甲基乙酯 N-(2-氨基乙基)-N'-[2-[2-(13-二十一碳烯基)-4,5-二氢-1H-咪唑-1-基]乙基]乙二胺 N-(2-氨基乙基)-N'-[2-(4,5-二氢-2-十九烷基-1H-咪唑-1-基)乙基]乙二胺 N-(2-氨基乙基)-N'-[2-(2-十七烷基-4,5-二氢-1H-咪唑-1-基)乙基]乙二胺 N,N,N',N'-四甲基-4,6-二(三甲基硅烷基)环戊二烯并[c]吡咯-1,3-二胺 N,N,N',N',5-戊甲基环戊并[c]吡咯-1,3-二胺 N,N,3,3-四甲基氮杂环丙烯-2-胺 N,5-二甲基-1,2-恶唑-3-胺 6H-吡唑并[1,5-c][1,2,3]三唑-3,5,6-三胺