3β-hydroxy-3',5'-dioxo-4'-phenyl-5,8<1',2'>-1',2',4'-triazolidino-5α,8α-ergosta-6,22-diene | 10123-90-7

• 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: 3β-hydroxy-3',5'-dioxo-4'-phenyl-5,8<1',2'>-1',2',4'-triazolidino-5α,8α-ergosta-6,22-diene
• 英文别名: (phenyl-4' urazolo-1',2')-5α,8α ergostadiene-6,22 ol-3β；3-hydroxy-2'-phenyl-[1,2,4]triazolo[1',2':6,7](6,7-diaza-5,8-etheno-ergost-22-ene)-3',5'-dione；(1S,2R,5R,6R,9R,10R,13S,15S)-5-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-13-hydroxy-6,10-dimethyl-18-phenyl-16,18,20-triazahexacyclo[13.5.2.01,9.02,6.010,15.016,20]docos-21-ene-17,19-dione
• CAS: 10123-90-7
• 化学式: C₃₆H₄₉N₃O₃
• 分子量: 571.803
• InChiKey: AEDMVIIBCHINBG-VHHKWQLYSA-N

物化性质

• 熔点：
  190-191.5 °C
• 沸点：
  641.2±65.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.25
• 重原子数：
  42.0
• 可旋转键数：
  5.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  69.16
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3β-hydroxy-3',5'-dioxo-4'-phenyl-5,8<1',2'>-1',2',4'-triazolidino-5α,8α-ergosta-6,22-diene 在 lithium 作用下， 以 氨 为溶剂， 生成 星鱼甾醇
  参考文献：
  名称：

  减少甾体5,7-二烯的7,8-双键的简单方法

  摘要：

  各种甾族5,7-二烯和4-苯基1-2-4三唑啉-3,5-二酮的1,4-Cycloadducts得到的可分离的混合物（3：2）的相应的Δ 5 -和Δ 7 -用溶解在回流的乙胺中的锂处理时，甾醇的收率很高。

  DOI：

  10.1039/c39820001169
• 作为产物：
  描述：

  benzoyloxy-3β (benzalamino-4' urazolo-1',2')-5α,8α ergostadiene-6,22 在 氢氧化钾 、 (PhSeO)2O 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 4.0h， 生成 3β-hydroxy-3',5'-dioxo-4'-phenyl-5,8<1',2'>-1',2',4'-triazolidino-5α,8α-ergosta-6,22-diene
  参考文献：
  名称：

  麦角固醇的1,2,4-三唑啉-3,5-二酮衍生物的改进合成方法及其将其转化为麦角固醇的新方法

  摘要：

  麦角固醇二烯系统以优异的产率与一系列的4-取代的1,2,4-三唑啉-3,5-二酮反应，所述一系列的4-取代的1,2,4-三唑啉-3,5-二酮是通过适当的酰肼与苯硒酸二酐或苯基硒酸的原位氧化而生成的。二芳基四氢呋喃和二苯硒酸也是有效的氧化剂。二烯体系可以通过碱水解而平滑地再生。

  DOI：

  10.1016/s0040-4039(00)88078-8

文献信息

• Solvent Compatibility of Poly(dimethylsiloxane)-Based Microfluidic Devices
  作者：Jessamine Ng Lee、Cheolmin Park、George M. Whitesides

  DOI：10.1021/ac0346712

  日期：2003.12.1

  This paper describes the compatibility of poly(dimethylsiloxane) (PDMS) with organic solvents; this compatibility is important in considering the potential of PDMS-based microfluidic devices in a number of applications, including that of microreactors for organic reactions. We considered three aspects of compatibility:  the swelling of PDMS in a solvent, the partitioning of solutes between a solvent and PDMS, and the dissolution of PDMS oligomers in a solvent. Of these three parameters that determine the compatibility of PDMS with a solvent, the swelling of PDMS had the greatest influence. Experimental measurements of swelling were correlated with the solubility parameter, δ (cal1/2 cm-3/2), which is based on the cohesive energy densities, c (cal/cm3), of the materials. Solvents that swelled PDMS the least included water, nitromethane, dimethyl sulfoxide, ethylene glycol, perfluorotributylamine, perfluorodecalin, acetonitrile, and propylene carbonate; solvents that swelled PDMS the most were diisopropylamine, triethylamine, pentane, and xylenes. Highly swelling solvents were useful for extracting contaminants from bulk PDMS and for changing the surface properties of PDMS. The feasibility of performing organic reactions in PDMS was demonstrated by performing a Diels−Alder reaction in a microchannel.

  本文描述了聚二甲基硅氧烷（PDMS）与有机溶剂的相容性；这种相容性在考虑基于PDMS的微流控设备在多个应用中的潜力时非常重要，包括作为有机反应的微反应器。我们考虑了相容性的三个方面：PDMS在溶剂中的膨胀、溶质在溶剂与PDMS之间的分配以及PDMS低聚物在溶剂中的溶解。在这三个决定PDMS与溶剂相容性的参数中，PDMS的膨胀影响最大。膨胀的实验测量与基于材料内聚能密度的溶解度参数δ（cal1/2 cm-3/2）相关联。对PDMS膨胀影响较小的溶剂包括水、硝基甲烷、二甲基亚砜、乙二醇、全氟三丁胺、全氟脱卡林、乙腈和碳酸丙烯酯；对PDMS膨胀影响较大的溶剂则是二异丙胺、三乙胺、戊烷和二甲苯。高膨胀溶剂对从大块PDMS中提取污染物及改变PDMS的表面性质非常有用。通过在微通道中进行Diels−Alder反应，展示了在PDMS中进行有机反应的可行性。
• Barton; Lusinchi; Sandoval Ramirez, Bulletin de la Societe Chimique de France, 1985, vol. NO. 5, # 5, p. 849 - 858
  作者：Barton、Lusinchi、Sandoval Ramirez

  DOI：——

  日期：——
• Shul'man, A. I.; Mikhailova, N. P.; Vyunov, K. A., Journal of general chemistry of the USSR, 1987, vol. 57, p. 2251 - 2252
  作者：Shul'man, A. I.、Mikhailova, N. P.、Vyunov, K. A.

  DOI：——

  日期：——
• Kondo, Fumihiro; Miyashita, Misako; Konno, Katsuhiro, Journal of the Chemical Society. Perkin transactions I, 1995, # 21, p. 2679 - 2680
  作者：Kondo, Fumihiro、Miyashita, Misako、Konno, Katsuhiro、Takayama, Hiroaki

  DOI：——

  日期：——
• Direct Interaction between Amphotericin B and Ergosterol in Lipid Bilayers As Revealed by ²H NMR Spectroscopy
  作者：Nobuaki Matsumori、Kazuaki Tahara、Hiroko Yamamoto、Atsushi Morooka、Mototsugu Doi、Tohru Oishi、Michio Murata

  DOI：10.1021/ja9033473

  日期：2009.8.26

  Although amphotericin B (AmB) is thought to exert its antifungal activity by forming transmembrane ion-permeable self-assemblies together with ergosterol, no previous study has directly proven AmB-ergosterol interaction. To establish the interaction, we measured H-2 NMR using deuterium-labeled sterols and AmB. The H-2 NMR spectra of deuterated ergosterol in palmitoyloleoylphosphatidylcholine (POPC) bilayers showed that fast axial diffusion of erogosterol was almost completely inhibited by the coexistence of AmB. Conversely, cholesterol mobility in POPC membrane was essentially unchanged with or without AmB. These results unequivocally demonstrate that ergosterol has significant interaction with AmB in POPC bilayers. In addition, we examined the mobility of AmB using deuterium-labeled AmB, and found that, although AmB is almost immobilized in sterol-free and cholesterol-containing POPC membranes, a certain ratio of AmB molecules acquires mobility in the presence of ergosterol. The similar mobility of AmB and ergosterol in POPC bilayers confirmed the idea of the direct intermolecular interaction between ergosterol and AmB.