(3α,5β,12α)-3-amino-12-hydroxycholan-24-oic acid methyl ester | 280765-90-4

• 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: (3α,5β,12α)-3-amino-12-hydroxycholan-24-oic acid methyl ester
• 英文别名: methyl 3α-amino-12α-hydroxy-5β-cholan-24-oate；methyl (4R)-4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3-amino-12-hydroxy-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: 280765-90-4
• 化学式: C₂₅H₄₃NO₃
• 分子量: 405.621
• InChiKey: OZSPROMXZQTIPK-JMKDMENQSA-N

物化性质

• 沸点：
  497.6±30.0 °C(Predicted)
• 密度：
  1.056±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  29
• 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：
  72.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3α,5β,12α)-3-amino-12-hydroxycholan-24-oic acid methyl ester 在 lithium hydroxide 、 三正丁胺 、 氯甲酸乙酯 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 为溶剂， 反应 12.17h， 生成 N-allyl-N'-methyl-3α-(3,5-dichlorobenzoyl)amino-12α-hydroxy-5β-cholan-24-amide
  参考文献：
  名称：

  Synthesis of deoxycholic-derived chiral stationary phases possessing both arylcarbamate and arylamide moieties: evaluation of their chiral discrimination properties in the HPLC resolution of racemic compounds

  摘要：

  Two families of chiral selectors derived from deoxycholic acid, possessing both an arylamide and an arylcarbamate group on the cholestanic backbone were synthesized and covalently bonded to silica gel to afford new chiral stationary phases (CSPs A1-D1 and A2-D2) for the HPLC resolution of racemic compounds. The chromatographic data concerning the resolution of selected racemic compounds on CSPs A1-D1 and A2-D2 were compared with those obtained using analogous CSPs possessing only arylcarbamate groups on the cholestanic system (CSPs A-D). This has allowed its to establish that the resolution capability of CSPs A1-D1 and A2-D2 depends not only on the position of the arylamide group on the cholestanic backbone, but also on the electronic characteristics of the aromatic substituents. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00490-6
• 作为产物：
  描述：

  去氧胆酸 在 4-二甲氨基吡啶 、 sodium azide 、 偶氮二甲酸二异丙酯 、 硫酸 、 三苯基膦 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 52.0h， 生成 (3α,5β,12α)-3-amino-12-hydroxycholan-24-oic acid methyl ester
  参考文献：
  名称：

  手性金属-有机笼中构象变化和配位体氢键的影响

  摘要：

  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。

  DOI：

  10.1021/acs.inorgchem.8b03610

文献信息

• Synthesis of proline derivatives of bile acids and their evaluation as organocatalysts in the asymmetric direct aldol reaction
  作者：Gian Luigi Puleo、Matteo Masi、Anna Iuliano

  DOI：10.1016/j.tetasy.2007.05.023

  日期：2007.6

  A new family of bile acid derived organocatalysts was obtained by linking l- or d-proline to amino derivatives of cholic and deoxycholic acids, which were used to promote the asymmetric direct aldol reaction between acetone and 4-nitrobenzaldehyde. Both the activity and enantioselectivity of the organocatalytic systems were dependent not only on the position of the proline moiety on the cholestanic

  通过将l-脯氨酸或d-脯氨酸与胆酸和脱氧胆酸的氨基衍生物连接，获得了一个新的胆汁酸衍生的有机催化剂家族，这些衍生物用于促进丙酮和4-硝基苯甲醛之间的不对称直接羟醛反应。有机催化体系的活性和对映选择性不仅取决于胆甾醇骨架上脯氨酸部分的位置及其绝对构型，还取决于甾体骨架上游离羟基的存在。最好的有机催化体系是在12位上带有d-脯氨酰胺部分，在3和7位带有游离羟基的胆酸衍生物，即使仅使用2％的催化剂负载量和ee高达80％。
• Blood pool agents for nuclear magnetic resonance diagnostics
  申请人：Bracco Imaging S.p.A.

  公开号：EP1935435B1

  公开（公告）日：2017-09-06
• Scale-Up of Trisodium [(3β,5β,12α)-3-[[4(<i>S</i>)-4-[Bis[2-[bis[(carboxy-<i>kO</i>)methyl]amino-<i>kN</i>]ethyl]amino-<i>kN</i>]-4-(carboxy-<i>kO</i>)-1-oxobutyl]amino]-12-hydroxycholan-24-oato(6-)]gadolinate(3-)], a Gd(III) Complex under Development As a Contrast Agent for MRI Coronary Angiography
  作者：Pier Lucio Anelli、Marino Brocchetta、Luciano Lattuada、Giuseppe Manfredi、Pierfrancesco Morosini、Marcella Murru、Daniela Palano、Marco Sipioni、Massimo Visigalli

  DOI：10.1021/op900008a

  日期：2009.7.17

  Process chemistry involved in the discovery and development routes to trisodium [(3 beta,5 beta,12(alpha)-3-[[4(S)-4-[bis[2-[bis[(carboxy-kO)methyl]amino-kN]ethyl]amino-kN]4-(carboxy-kO)-1-oxobutyl]- amino]-12-hydroxycholan-24-oato(6-)]gadolinate(3-)] (B22956/1) starting from L-glutamic acid and (3 alpha,5 beta,12 alpha)-3,12-dihydroxycholan-24-oic acid is described. The best process is based on seven chemical steps and overcomes difficult purification protocols. Such process has been successfully implemented to prepare multikilogram batches of the target compound in 20% overall yield from (3 alpha,5 beta,12 alpha)-3,12-dihydroxycholan-24-oic acid.
• BLOOD POOL AGENTS FOR NUCLEAR MAGNETIC RESONANCE DIAGNOSTICS
  申请人：BRACCO IMAGING S.p.A.

  公开号：EP1140209B1

  公开（公告）日：2008-08-20