methyl 3,7,12-trimethoxycholanoate | 75469-14-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: methyl 3,7,12-trimethoxycholanoate
• 英文别名: 3α,7α,12α-trimethoxy-5β-cholanic acid methyl ester；(R)-methyl 4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trimethoxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate；methyl (4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trimethoxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate
• CAS: 75469-14-6
• 化学式: C₂₈H₄₈O₅
• 分子量: 464.686
• InChiKey: DUZBDLNNTQLDSA-SREHDYERSA-N

物化性质

• 沸点：
  505.6±50.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3,7,12-trimethoxycholanoate 在 4-二甲氨基吡啶 、 正丁基锂 、 水 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 38.25h， 生成 (4R)-tert-butyl 2-methyl-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trimethoxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentaneperoxoate
  参考文献：
  名称：

  氟转移到烷基自由基

  摘要：

  随着含氟药物的重要性不断提高，有机化合物选择性氟化新合成技术的发展也在增加。可能适用于药物合成的传统方法依赖于使用离子形式的氟（F(-)​​ 或 F(+)）。激进的方法虽然作为一种补充方法具有潜在吸引力，但由于缺乏安全的原子氟 (F(•)) 来源而受到阻碍。已开发出一种新的烷基氟化方法，该方法利用试剂 N-氟苯磺酰亚胺作为氟转移剂到烷基自由基。这种方法适用于广泛的烷基自由基，包括伯、仲、叔、苄基和杂原子稳定的自由基。此外，计算表明，含氟离子试剂可能是将这种方法进一步扩展到极性反应介质的候选者。在烷基自由基氟化中使用这些试剂有可能实现强大的新转化，否则将需要多个合成步骤。

  DOI：

  10.1021/ja211679v
• 作为产物：
  描述：

  胆酸 在 氯化亚砜 、 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 38.17h， 生成 methyl 3,7,12-trimethoxycholanoate
  参考文献：
  名称：

  氟转移到烷基自由基

  摘要：

  随着含氟药物的重要性不断提高，有机化合物选择性氟化新合成技术的发展也在增加。可能适用于药物合成的传统方法依赖于使用离子形式的氟（F(-)​​ 或 F(+)）。激进的方法虽然作为一种补充方法具有潜在吸引力，但由于缺乏安全的原子氟 (F(•)) 来源而受到阻碍。已开发出一种新的烷基氟化方法，该方法利用试剂 N-氟苯磺酰亚胺作为氟转移剂到烷基自由基。这种方法适用于广泛的烷基自由基，包括伯、仲、叔、苄基和杂原子稳定的自由基。此外，计算表明，含氟离子试剂可能是将这种方法进一步扩展到极性反应介质的候选者。在烷基自由基氟化中使用这些试剂有可能实现强大的新转化，否则将需要多个合成步骤。

  DOI：

  10.1021/ja211679v

文献信息

• Room-Temperature Direct Alkynylation of Arenes with Copper Acetylides
  作者：Cédric Theunissen、Gwilherm Evano

  DOI：10.1021/ol502030y

  日期：2014.9.5

  C–H bond in azoles and polyhalogenated arenes can be smoothly activated by copper acetylides to give the corresponding alkynylated (hetero)arenes by simple reaction at room temperature in the presence of phenanthroline and lithium tert-butoxide under an oxygen atmosphere. These stable, unreactive, and readily available polymers act as especially efficient and practical reagents for the introduction

  唑和多卤代芳烃中的C–H键可以通过乙炔铜平滑活化，在氧气气氛下，在邻菲咯啉和叔丁醇锂存在下，在室温下通过简单反应，得到相应的炔基化（杂）芳烃。这些稳定的，无反应性的和容易获得的聚合物充当特别有效和实用的试剂，用于在非常温和的条件下将炔基引入众多的芳烃中。
• A Supramolecular Ion Channel Based on Amphiphilic Cholic Acid Derivatives
  作者：Yoshiaki Kobuke、Takeshi Nagatani

  DOI：10.1246/cl.2000.298

  日期：2000.4

  Cholic acid was modified so as to represent the simplest expression of an artificial supramolecular ion channel by converting three hydroxyls to methyl ethers and a carboxyl to a methylene(trimethyl)ammonium grouping. It gave stable single channel currents showing several conductance values in planar bilayer lipid membrane.

  通过将三个羟基转化为甲基醚，将一个羧基转化为亚甲基（三甲基）铵基团，对胆酸进行了改性，从而代表了人工超分子离子通道的最简单表达方式。它在平面双层脂膜中产生了稳定的单通道电流，显示出多个电导值。
• Anion-Selective Cholesterol Decorated Macrocyclic Transmembrane Ion Carriers
  作者：Harekrushna Behera、Nandita Madhavan

  DOI：10.1021/jacs.7b07479

  日期：2017.9.20

  Anion transporters play a vital role in cellular processes and their dysregulation leads to a range of diseases such as cystic fibrosis, Bartters syndrome and epilepsy. Synthetic chloride transporters are known to induce apoptosis in cancer cell lines. Herein, we report triamide macrocycles that are easily synthesized and externally functionalized by pendant membrane-permeable groups. Among a variety of chains appended onto the macrocycle scaffold, cholesterol is found to be the best with an EC50 value of 0.44 mu M. The macrocycle is highly anion-selective and transports ions via an OH-/X- antiport mechanism. The macrocycle is an interesting scaffold for ion-transport as it is able to discriminate between various anions and shows a preference for SCN- and Cl-. Such anion-selective transporters are highly attractive model systems to study ion-transport mechanisms and could potentially be of high therapeutic value.
• Ion Conductors Derived from Cholic Acid and Spermine:  Importance of Facial Hydrophilicity on Na⁺ Transport and Membrane Selectivity
  作者：Prasun Bandyopadhyay、Vaclav Janout、Lan-hui Zhang、Steven L. Regen

  DOI：10.1021/ja010926m

  日期：2001.8.1

  A series of ion conductors have been synthesized in which the degree of facial hydrophilicity has been systematically varied. Specifically, conjugates have been prepared from cholic acid and spermine in which the hydrophilic face of each sterol bears methoxy (1), hydroxy (2), carbamate (3), or sulfate groups (4). The ability of these conjugates to promote the transport of Na+ across phosphatidylcholine membranes of varying thickness has been investigated by Na-23 NMR spectroscopy. Examination of observed activities in three different phosphatidylcholine membranes has provided evidence for membrane-spanning dimers as the transport-active species. In the thinnest membranes investigated, made from 1,2-dimyristoleoyl-sn-glycero-3-phosphocholine (C14), Na+-transport activity was found to increase, substantially, with increasing facial hydrophilicity. In thicker membranes, made from 1,2-dioleoyl-sn-glycero-3-phosphocholine (C18), observed activities were found to decrease with increasing facial hydrophilicity; with a membrane of intermediate thickness, prepared from 1,2-dipalmitoleoyl-sn-glycero-3-phosphocholine (C16), ion-conducting activity increased and then decreased, with continuous increases in facial hydrophilicity. The possible origins for these variations in activity are briefly discussed.