(R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Trimethoxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentan-1-ol | 272115-35-2

• 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,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Trimethoxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentan-1-ol
• 英文别名: (R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trimethoxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentan-1-ol
• CAS: 272115-35-2
• 化学式: C₂₇H₄₈O₄
• 分子量: 436.676
• InChiKey: WSIPMKKUVCUFIJ-XJZYBRFWSA-N

物化性质

• 沸点：
  504.8±50.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.32
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  47.92
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Trimethoxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentan-1-ol 在 氯化亚砜 作用下， 以 吡啶 为溶剂， 以79%的产率得到(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-17-((R)-4-Chloro-1-methyl-butyl)-3,7,12-trimethoxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthrene
  参考文献：
  名称：

  A Supramolecular Ion Channel Based on Amphiphilic Cholic Acid Derivatives

  摘要：

  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。

  DOI：

  10.1246/cl.2000.298
• 作为产物：
  描述：

  methyl 3,7,12-trimethoxycholanoate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到(R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Trimethoxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentan-1-ol
  参考文献：
  名称：

  A Supramolecular Ion Channel Based on Amphiphilic Cholic Acid Derivatives

  摘要：

  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。

  DOI：

  10.1246/cl.2000.298

文献信息

• A Bifunctional Copper Catalyst Enables Ester Reduction with H₂: Expanding the Reactivity Space of Nucleophilic Copper Hydrides
  作者：Birte M. Zimmermann、Trung Tran Ngoc、Dimitrios-Ioannis Tzaras、Trinadh Kaicharla、Johannes F. Teichert

  DOI：10.1021/jacs.1c09626

  日期：2021.10.13

  activation of esters through hydrogen bonding and formation of nucleophilic copper(I) hydrides from H2, resulting in a catalytic hydride transfer to esters. The reduction step is further facilitated by a proton shuttle mediated by the guanidinium subunit. This bifunctional approach to ester reductions for the first time shifts the reactivity of generally considered “soft” copper(I) hydrides to previously

  采用基于铜 (I)/NHC 配合物和胍有机催化剂的双功能催化剂，促进了以 H 2作为末端还原剂的催化酯还原成醇。这里采用的方法能够通过氢键同时活化酯，并从 H 2形成亲核的氢化铜 (I) ，从而导致氢化物催化转移到酯。由胍亚基介导的质子穿梭进一步促进了还原步骤。这种酯还原的双功能方法首次将通常认为的“软”氢化铜 (I) 的反应性转变为以前不反应的“硬”酯亲电子试剂，并为用催化剂和 H 2替代化学计量还原剂铺平了道路.
• Nonheme Iron-Mediated Amination of C(sp³)–H Bonds. Quinquepyridine-Supported Iron-Imide/Nitrene Intermediates by Experimental Studies and DFT Calculations
  作者：Yungen Liu、Xiangguo Guan、Ella Lai-Ming Wong、Peng Liu、Jie-Sheng Huang、Chi-Ming Che

  DOI：10.1021/ja3122526

  日期：2013.5.15

  (1, qpy = 2,2':6',2″:6″,2''':6''',2''''-quinquepyridine) is a highly active nonheme iron catalyst for intra- and intermolecular amination of C(sp(3))-H bonds. This complex effectively catalyzes the amination of limiting amounts of not only benzylic and allylic C(sp(3))-H bonds of hydrocarbons but also the C(sp(3))-H bonds of cyclic alkanes and cycloalkane/linear alkane moieties in sulfamate esters,

  7配位络合物[Fe(qpy)(MeCN)2](ClO4)2 (1, qpy = 2,2':6',2″:6″,2''':6''',2' '''-quinquepyridine) 是一种高活性的非血红素铁催化剂，用于 C(sp(3))-H 键的分子内和分子间胺化。该复合物不仅有效地催化有限量的烃的苄基和烯丙基 C(sp(3))-H 键的胺化，而且还催化环烷烃和环烷烃/线性烷烃部分的 C(sp(3))-H 键的胺化。氨基磺酸酯，例如衍生自薄荷烷和甾体胆烷和雄甾烷的那些，使用PhI=NR或“PhI(OAc)2+H2NR”[R=Ts(对甲苯磺酰基)，Ns(对硝基苯磺酰基)]作为氮源，胺化产物的分离率高达 93%。亚铁酰亚胺/氮烯中间体 [Fe(qpy)(NR)(X)](n+) (CX, X = NR, 溶剂, 或阴离子）在实验研究的基础上提出，包括 ESI-MS 分析、交叉实验、哈米特图以及与 CH
• 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.
• Steric and Magnetic Asymmetry Distinguished by Encapsulation
  作者：Toru Amaya、Julius Rebek

  DOI：10.1021/ja049043w

  日期：2004.5.1

  Guests in an achiral cavity experience asymmetric magnetic environments induced by chiral centers outside the cavity.
• 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。