Formic acid (3R,5R,8R,9S,10S,12S,13R,14S,17R)-17-[(R)-3-(2-dimethylamino-ethylcarbamoyl)-1-methyl-propyl]-12-formyloxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester | 820965-73-9

• 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: Formic acid (3R,5R,8R,9S,10S,12S,13R,14S,17R)-17-[(R)-3-(2-dimethylamino-ethylcarbamoyl)-1-methyl-propyl]-12-formyloxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester
• CAS: 820965-73-9
• 化学式: C₃₀H₅₀N₂O₅
• 分子量: 518.737
• InChiKey: SKDWBQGECYQAIW-KJJSHBOESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.43
• 重原子数：
  37.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  84.94
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Formic acid (3R,5R,8R,9S,10S,12S,13R,14S,17R)-17-[(R)-3-(2-dimethylamino-ethylcarbamoyl)-1-methyl-propyl]-12-formyloxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 14.0h， 以60%的产率得到(4R)-4-[(3R,10S,12S,13R,17R)-3,12-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]-N-(2-dimethylaminoethyl)pentanamide
  参考文献：
  名称：

  Structure and Dynamics of a Molecular Hydrogel Derived from a Tripodal Cholamide

  摘要：

  Tripodal cholamide 1 is a supergelator of aqueous fluids. A variety of physical techniques, including cryo-transmission electron microscopy (TEM), circular dichroism (CD), steady-state fluorescence, time-resolved fluorescence, and dynamic light-scattering, were employed to understand the structure and dynamics of the gel. Fluorescent probes [ANS (8-anilinonaphthalene-1-sulfonic acid) and pyrene] reported two critical aggregation concentrations (CAC(1) and CAC(2)) of 1 in predominantly aqueous media, with the minimum gel concentration (MGC) being close to CAC(2). Fluorescence lifetime measurements with pyrene revealed ineffective quenching of pyrene fluorescence by oxygen, possibly caused by slower Brownian diffusion due to the enhanced viscosity in the gel phase. The study of the gelation kinetics by monitoring the ultrafast dynamics of ANS revealed a progressive increase in the aggregate size and the microviscosity of the aqueous pool encompassed by the self-assembled fibrillar network (SAFIN) during the gelation. The striking difference between microviscosity and bulk (macroscopic) viscosity of the gel is also discussed.

  DOI：

  10.1021/ja046788t
• 作为产物：
  描述：

  3α,12α-diformyloxy-5β-cholan-24-oic acid 、 N,N-二甲基乙二胺 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.08h， 以59%的产率得到Formic acid (3R,5R,8R,9S,10S,12S,13R,14S,17R)-17-[(R)-3-(2-dimethylamino-ethylcarbamoyl)-1-methyl-propyl]-12-formyloxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester
  参考文献：
  名称：

  Structure and Dynamics of a Molecular Hydrogel Derived from a Tripodal Cholamide

  摘要：

  Tripodal cholamide 1 is a supergelator of aqueous fluids. A variety of physical techniques, including cryo-transmission electron microscopy (TEM), circular dichroism (CD), steady-state fluorescence, time-resolved fluorescence, and dynamic light-scattering, were employed to understand the structure and dynamics of the gel. Fluorescent probes [ANS (8-anilinonaphthalene-1-sulfonic acid) and pyrene] reported two critical aggregation concentrations (CAC(1) and CAC(2)) of 1 in predominantly aqueous media, with the minimum gel concentration (MGC) being close to CAC(2). Fluorescence lifetime measurements with pyrene revealed ineffective quenching of pyrene fluorescence by oxygen, possibly caused by slower Brownian diffusion due to the enhanced viscosity in the gel phase. The study of the gelation kinetics by monitoring the ultrafast dynamics of ANS revealed a progressive increase in the aggregate size and the microviscosity of the aqueous pool encompassed by the self-assembled fibrillar network (SAFIN) during the gelation. The striking difference between microviscosity and bulk (macroscopic) viscosity of the gel is also discussed.

  DOI：

  10.1021/ja046788t