(R)-4-((3R,5R,8R,9S,10S,13R,14S,17R)-3-methoxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid | 78072-68-1

• 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: (R)-4-((3R,5R,8R,9S,10S,13R,14S,17R)-3-methoxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid
• 英文别名: (4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-methoxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
• CAS: 78072-68-1
• 化学式: C₂₅H₄₂O₃
• 分子量: 390.607
• InChiKey: AFKLMJZGGLNETD-ULCLHEGSSA-N

物化性质

• 沸点：
  496.6±18.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  28
• 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：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-4-((3R,5R,8R,9S,10S,13R,14S,17R)-3-methoxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid 在 lithium aluminium tetrahydride 、 四溴化碳 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 55.0h， 生成
  参考文献：
  名称：

  一类带有刚性疏水基团的新型两亲物，用于膜蛋白的溶解和稳定

  摘要：

  非传统两亲剂：赋予膜蛋白水溶性通常需要使用去污剂或其他两亲剂。基于甾体亲脂基团合成了一类新的两亲物，并用几种膜蛋白进行了评估。结果表明，相对于流行的传统去污剂，如十二烷基麦芽糖苷 (DDM)，新型两亲物“糖基薯蓣皂苷元”（GDN；见图）可增强溶液中多种膜蛋白的稳定性。

  DOI：

  10.1002/chem.201200069
• 作为产物：
  描述：

  3-Alpha-羟基-5-beta-24-胆烷酸甲酯 在 sodium hydroxide 、 乙醇 、 silver(l) oxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 98.0h， 生成 (R)-4-((3R,5R,8R,9S,10S,13R,14S,17R)-3-methoxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid
  参考文献：
  名称：

  Structure-Activity Relationships of Cytotoxic Cholesterol-Modified DNA Duplexes

  摘要：

  Short DNA duplexes with cholesterol linked at the 3'-terminus of each strand have unique, selective cytotoxic properties. The structural requirements for biological activity were explored through chemical synthesis of analogs and testing in cultured hepatoma cells. Effects of modifications to the sequence, backbone, 3'-sterol, 3'-linker, and 5'-terminus were evaluated. Self-complementary 3'-modified oligodeoxynucleotide (ODN) 10-mers were prepared from solid supports bearing the modification and linker of interest. Any changes to the normal phosphodiester backbone were poorly tolerated. The presence of cholesterol or a closely related sterol was an absolute requirement for activity. The length and position of attachment of the linker to cholesterol was important, with longer linkers showing reduced activity. Large, lipophilic groups at the 5'-terminus gave reduced cytotoxicity and poor solubility properties. The short length and unique structure of these ODNs allowed efficient automated synthesis on a 400 mu mol scale and simplified purification.

  DOI：

  10.1021/jm00022a025

文献信息

• Photoinduced <scp>NaI‐Promoted</scp> Radical Borylation of Alkyl Halides and Pseudohalides
  作者：Chenglan Wang、Lu Zhou、Kai Yang、Feng Zhang、Qiuling Song

  DOI：10.1002/cjoc.202100115

  日期：2021.7

  A method for photoinduced NaI-promoted radical borylation of aliphatic halides and pseudohalides with bis(catecholato)diboron (B2cat2) as the boron source is introduced. The borylation reaction is operationally simple and shows high functional group tolerance and broad substrate scope. Preliminary mechanistic studies suggest that the reaction proceeds through SN2-based radical-generation strategy.

  介绍了一种以双(儿茶酚)二硼(B 2 cat 2 )为硼源的光诱导NaI促进的脂肪族卤化物和拟卤化物自由基硼化的方法。硼酸化反应操作简单，显示出高官能团耐受性和广泛的底物范围。初步机理研究表明，该反应通过基于S N 2 的自由基生成策略进行。
• Stereoselective Synthesis of Z Fluoroalkenes through Copper-Catalyzed Hydrodefluorination of <i>gem</i> -Difluoroalkenes with Water
  作者：Jiefeng Hu、Xiaowei Han、Yu Yuan、Zhuangzhi Shi

  DOI：10.1002/anie.201708224

  日期：2017.10.16

  A copper catalytic system was established for the stereoselective hydrodefluorination of gem‐difluoroalkenes through C−F activation to synthesize various Z fluoroalkenes. H2O is used as the hydrogen source for the fluorine acceptor moiety. This mild catalytic system shows good‐functional group compatibility, accepting a range of carbonyls as precursors to the gem‐difluoroalkenes, including aliphatic

  建立了铜催化体系，用于通过C-F活化来合成各种Z 氟烯烃，以进行宝石二氟烯烃的立体选择性加氢脱氟。H 2 O用作氟受体部分的氢源。这种温和的催化体系显示出良好的官能团相容性，可以接受多种羰基化合物作为双二氟烯烃的前体，包括脂族，芳族和α，β-不饱和醛，甚至酮。它是复杂化合物后期修饰的有力合成方法。
• AMPHIPHILIC COMPOUNDS
  申请人：WISCONSIN ALUMNI RESEARCH FOUNDATION

  公开号：US20130266656A1

  公开（公告）日：2013-10-10

  Bringing membrane proteins into aqueous solution generally requires the use of detergents or other amphiphilic agents. The invention provides a new class of amphiphiles, each of which includes a multi-fused ring system as a lipophilic group. These new amphiphiles confer enhanced stability to a range of membrane proteins in solution relative to conventional detergents, leading to improved structural and functional stability of membrane proteins, including integral membrane proteins. Accordingly, the invention provides new amphiphiles for biochemical manipulations and characterization of membrane proteins. These amphiphiles display favorable behavior with membrane proteins and can be used to aid the solubilization, isolation, purification, stabilization, crystallization, and/or structural determination of membrane proteins.

  将膜蛋白引入水溶液通常需要使用洗涤剂或其他两性分子试剂。该发明提供了一类新型两性分子，每种都包括一个多融合环系统作为亲脂基团。这些新型两性分子相对于传统洗涤剂在溶液中赋予了一系列膜蛋白增强的稳定性，从而提高了膜蛋白的结构和功能稳定性，包括整合膜蛋白。因此，该发明提供了用于生化操作和膜蛋白表征的新型两性分子。这些两性分子与膜蛋白表现出良好的行为，并可用于辅助膜蛋白的溶解、分离、纯化、稳定化、结晶和/或结构测定。
• Copper-Catalyzed Asymmetric Defluoroborylation of 1-(Trifluoromethyl)Alkenes
  作者：Pan Gao、Chengkai Yuan、Yue Zhao、Zhuangzhi Shi

  DOI：10.1016/j.chempr.2018.07.003

  日期：2018.9

  copper-catalyzed defluoroborylation of 1-(trifluoromethyl)alkenes with B2pin2 is described. The reaction conditions were mild, and a variety of common functional groups, such as ether, fluoride, chloride, bromide, iodide, ester, cyano, sulfide, amino, and indoyl groups, were well tolerated. Furthermore, we not only applied this developed system as a powerful synthetic tool for the late-stage modification

  宝石-二氟烯烃具有类似于酮，醛和酯的立体和电子构型，因此在现代药物发现中已广泛用作羰基等排体。尽管已经进行了许多尝试来获得宝石-二氟烯烃，但是在宝石-二氟乙烯基的α位上诱导对映选择性仍然是一个挑战。这里，为了建造一种有效的方法宝石经由1-（三氟甲基）烯烃的铜-催化的defluoroborylation具有高对映体过量-difluoroallylboronates与乙2销2描述。反应条件温和，对各种常见的官能团（如醚，氟，氯，溴，碘，酯，氰基，硫化物，氨基和吲哚基）具有良好的耐受性。此外，我们不仅将此开发的系统用作复杂化合物后期修饰的强大合成工具，还强调了所形成化合物在合成中的实用性。
• Copper-catalysed, diboron-mediated <i>cis</i>-dideuterated semihydrogenation of alkynes with heavy water
  作者：Xiaowei Han、Jiefeng Hu、Cheng Chen、Yu Yuan、Zhuangzhi Shi

  DOI：10.1039/c9cc03213d

  日期：——

  efficiently mediate the transfer of two D atoms from heavy water directly onto alkynes through copper-catalysed cis-selective semihydrogenation. Avoiding the use of costly and flammable D2 gas, this safe and practical process can proceed with excellent chemoselectivity and stereoselectivity. Utilizing the present method as the key step, the formal asymmetric total synthesis of d2-deuterium-labeled cis-combretastatin

  将氘原子结合到有机分子中的方法对制药业来说很有价值。在这里，我们发现二硼试剂可以通过铜催化的顺式选择性半氢化作用有效地介导两个D原子从重水直接转移到炔烃上。避免使用昂贵且易燃的D 2气体，该安全实用的过程可以进行出色的化学选择性和立体选择性。使用本方法作为关键步骤，证明了d2-氘标记的顺式-combretastatin A4的形式不对称全合成。机理研究表明，炔烃的单硼化是该半氢化过程的关键步骤。