(3a,5b,7a,12a)-3-氨基-7,12-二羟基胆甾烷-24-酸甲酯 | 142975-31-3

• 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
• 中文名称: (3a,5b,7a,12a)-3-氨基-7,12-二羟基胆甾烷-24-酸甲酯
• 中文别名: 3A-氨基胆酸甲酯
• 英文名称: methyl 3β-amino-7α,12α-dihydroxy-5β-cholane-24-oate
• 英文别名: (3a,5b,7a,12a)-3-Amino-7,12-dihydroxycholan-24-oic acid methyl ester；methyl (4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-amino-7,12-dihydroxy-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: 142975-31-3
• 化学式: C₂₅H₄₃NO₄
• 分子量: 421.621
• InChiKey: AVHAEQZRKMRLKH-SRNOMOOLSA-N

物化性质

• 沸点：
  530.9±50.0 °C(Predicted)
• 密度：
  1.107

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  92.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3a,5b,7a,12a)-3-氨基-7,12-二羟基胆甾烷-24-酸甲酯 在 水 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-{3-[4-(3-amino-7,12-dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoylamino]-7,12-dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl}-pentanoic acid methyl ester
  参考文献：
  名称：

  Oligomeric Cholates:  Amphiphilic Foldamers with Nanometer-Sized Hydrophilic Cavities

  摘要：

  The hydroxyl at the C-3 of cholic acid was converted to an amino group, and the resulting aminofunctionalized cholic acid was used as a monomer to prepare amide-linked oligomeric cholates. These cholate oligomers fold into helical structures with nanometer-sized hydrophilic internal cavities in solvent mixtures consisting of mostly nonpolar solvents such as carbon tetrachloride or ethyl acetate/hexane and 2-5% of a polar solvent such as methanol or DMSO. The conformations of the foldamers; were studied by UV, fluorescence, fluorescence quenching, and fluorescence resonance energy transfer. The nature of the polar/nonpolar solvents and their miscibility strongly influenced the folding reaction. Folding was cooperative, as evidenced by the sigmoidal curves in solvent denaturation experiments. The folded conformers became more stable with an increase in the chain length. The folding/unfolding equilibrium was highly sensitive toward the amount of polar solvent. One percent variation in the solvent composition could change the folding free energies by 0.5-1.4 kcal/mol.

  DOI：

  10.1021/ja056151p
• 作为产物：
  描述：

  胆酸甲酯 在 吡啶 、 sodium azide 、 palladium 10% on activated carbon 、 甲酸铵 作用下， 以 甲醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 (3a,5b,7a,12a)-3-氨基-7,12-二羟基胆甾烷-24-酸甲酯
  参考文献：
  名称：

  Two-channel dansyl/tryptophan emitters with a cholic acid bridge as reporters for local hydrophobicity within supramolecular systems based on bile salts

  摘要：

  在仿生介质中，由于碘离子的存在，与Trp和Dns荧光团结合的偶联双聚体同时发射的发射被抑制，其速率常数取决于局部疏水性。

  DOI：

  10.1039/c4ob01394h

文献信息

• Improving reactivity and selectivity of aqueous-based Heck reactions by the local hydrophobicity of phosphine ligands
  作者：Gina M. Roberts、Shiyong Zhang、Yan Zhao、L. Keith Woo

  DOI：10.1016/j.tet.2015.09.010

  日期：2015.10

  affords a new ligand, 1, which is effective in palladium-catalyzed Heck cross-couplings between acrylates and aryl iodides under mild, aqueous reaction conditions. High yields, up to 99%, were achieved in water at 40 °C. In competition studies, a more hydrophobic substrate (n-Bu acrylate) was preferred over the least hydrophobic substrate (methyl acrylate), supportive of a localized hydrophobic microenvironment

  用胆酸盐部分的三芳基膦的变形，得到一个新的配体，1，这是有效的钯催化的Heck交叉偶联丙烯酸酯和芳基碘之间温和，含水反应条件下进行。在40°C的水中可实现高达99％的高收率。在竞争研究中，更疏水基质（Ñ -Bu丙烯酸酯）中的溶液，优选在至少疏水性基材（丙烯酸甲酯），支持靠近催化中心的局部微环境的疏水性的。当本地疏水性是使用标准的水溶性膦或在有机溶剂中消除了疏水性衬底的增强的反应性和选择性消失。
• <b>A Multiple Multicomponent Approach to Chimeric Peptide-Peptoid Podands</b>
  作者：Daniel G. Rivera、Fredy León、Odette Concepción、Fidel E. Morales、Ludger A. Wessjohann

  DOI：10.1002/chem.201201591

  日期：2013.5.10

  (pseudo)peptidic receptors, a new approach based on multiple Ugi four‐component reactions (Ugi‐4CR) is proposed as a means of simultaneously incorporating several binding and catalytic elements into organizing scaffolds. By employing α‐amino acids either as the amino or acid components of the Ugi‐4CRs, this multiple multicomponent process allows for the one‐pot assembly of podands bearing chimeric peptide–peptoid

  传统上，多臂，基于肽的受体在超分子化学中的成功不仅取决于序列，而且同样取决于各种肽链的适当定位以创建结合元件的多价阵列。作为对（伪）肽受体的一种更快，更通用和替代的访问方式，提出了一种基于多种Ugi四组分反应（Ugi-4CR）的新方法，作为将几种结合和催化元素同时整合到组织支架中的一种手段。通过使用α-氨基酸作为Ugi-4CRs的氨基酸或酸成分，这种多组分过程允许一锅组装带有嵌合肽-类肽链作为附加臂的豆荚。碗形的三脚架 凹形多功能骨架被用作拓扑上多样化的平台，用于定位由Ugi-4CRs形成的多个肽链。用类似的方法，合成了具有几个轴向异氰酸酯基的甾体结构单元，并利用其将构象约束的嵌合链对齐，从而为经典的肽-甾体受体提供了另一种选择。分支和杂合的肽-类肽附属物为合成受体的合理设计和组合生产提供了新的可能性。该概念也可扩展到其他多组分反应。合成了具有几个轴向异氰酸酯基的甾体结构单元，并利用其将构
• Influence of Conformational Change and Interligand Hydrogen Bonding in a Chiral Metal–Organic Cage
  作者：Shovan Kumar Sen、Ramalingam Natarajan

  DOI：10.1021/acs.inorgchem.8b03610

  日期：2019.6.3

  We report about the coordination-driven self-assembly of a chiral bis-pyridyl ligand (1), synthesized from steroidal cholic acid, with Pd(II) ions to form a chiral metal–organic Pd2(1)4 cage. The self-assembly of the cage was facilitated by favorable conformational change in the alkyl chain of the cholic acid. Interligand hydrogen bonding played a crucial role in directing the formation of a C4 symmetric

  我们报道了由甾体胆酸与Pd（II）离子合成形成手性金属-有机Pd 2（1）4笼的手性双吡啶基配体（1）的协调驱动自组装。胆酸的烷基链中有利的构象变化促进了笼的自组装。DFT研究表明，配体氢键在指导不同可能异构体之间C 4对称笼的形成中起着至关重要的作用，正如DFT研究和使用不同配体的对照实验所表明的那样。
• One-Pot Mitsunobu-Staudinger Preparation of 3-Aminocholan-24-oic Acid Esters from 3-Hydroxycholan-24-oic Acid Esters
  作者：Pier Lucio Anelli、Luciano Lattuada、Fulvio Uggeri

  DOI：10.1080/00397919808005079

  日期：1998.1

  Abstract 3-Hydroxycholan-24-oic acid esters are easily converted into the corresponding 3-amino derivatives via Mitsunobu reaction with diphenylphosphoryl azide (DPPA) and Staudinger reduction with PPh3/H2O of the intermediate azido compound in THF.

  摘要 3-Hydroxycholan-24-oic酸酯通过与叠氮磷(DPPA)的Mitsunobu反应和中间体叠氮化合物在THF中的PPh3/H2O进行Staudinger还原反应，很容易转化为相应的3-氨基衍生物。
• Steroidal guanidinium receptors for the enantioselective recognition of N-acyl α-amino acids
  作者：Anthony P. Davis、Laurence J. Lawless

  DOI：10.1039/a808245f

  日期：——

  Guanidinium cations 4 and 5 extract N-acetyl α-amino acids into CHCl3 from an aqueous medium with enantiomeric excesses of up to 80%.

  胍盐阳离子 4 和 5 将 N-乙酰基 α-氨基酸从水性介质中萃取到 CHCl3 中，对映体过量高达 80%。