岩配基 | 16653-52-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: 岩配基
• 英文名称: 3β,12β-dihydroxy-(25R)-5α-spirostane
• 英文别名: (25R)-5α-spirostane-3β,12β-diol；(25R)-5α-spirostan-3β,12β-diol；5α,25R-spirostan-3β,12β-diol；17β-Dihydrohecogenin；rockogenin；OR-885；(1R,2S,4S,5'R,6R,7S,8R,9S,10R,12S,13S,16S,18S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-10,16-diol
• CAS: 16653-52-4
• 化学式: C₂₇H₄₄O₄
• 分子量: 432.644
• InChiKey: BQNMOLSYHYSCMS-TUUYSWIFSA-N

物化性质

• 沸点：
  550.5±50.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)
• 熔点：
  221 °C

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  31
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  岩配基 在 吡啶 、 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 sodium hydroxide 、 双氧水 、 双(三甲基硅烷基)氨基钾 、 氯化铵 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 55.59h， 生成 3β,12β-di(t-butyldimethylsilyloxy)-16α,17α-oxido-20-trifluoromethanesulfonyloxy-5α-pregn-20-ene
  参考文献：
  名称：

  Pd催化反应中的α，β-环氧乙烯基三氟甲磺酸酯。

  摘要：

  [反应：见正文]描述了在Pd催化的反应中甾体α，β-环氧乙烯基三氟甲磺酸酯的反应。Pd（0）氧化插入CO键产生乙烯基钯12的速度快于由乙烯基环氧化物形成pi-烯丙基衍生物的速度。尽管可以在某些条件下捕获12，但最终它会重排为烷醇钯14，与15和/或10处于平衡状态。

  DOI：

  10.1021/ol000064e
• 作为产物：
  描述：

  龙舌兰皂苷乙酯 在 sodium tetrahydroborate 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 岩配基
  参考文献：
  名称：

  Synthesis and Biological Activity Of Unsymmetrical Bis-Steroidal Pyrazines Related to the Cytotoxic Marine Natural Product Cephalostatin 1

  摘要：

  A mild, high-yielding synthesis of symmetrical steroidal pyrazines was achieved from the dimerization of 2-amino-3-ketosteroids, which were produced in situ from the triphenylphosphine-water reduction of the corresponding alpha-azido ketone. 2-Azidocholestan-3-one gave the dimeric steroidal pyrazine very cleanly, and two known dimeric pyrazines based on androstanone were also made using this methodology. Both C-2-symmetric geometric isomers of the dimeric steroidal pyrazine derived from cholestane were prepared by reaction of 2,3-diaminocholestane with cholestane-2,3-dione. A route to unsymmetrical bis-steroidal pyrazines was based on the observation that alpha-acetoxy ketones react with alpha-amino oximes directly with no need for oxidation of intermediate dihydropyrazines. Heating either 2 beta,17 beta-dihydroxyandrostan-3-one diacetate or 2 beta,17 beta-dihydroxyhecogenin-3-one diacetate with 2-amino-3-methoxyiminocholestane in toluene at 145 degrees C gave the corresponding unsymmetrical pyrazine in moderate yield. Five of the steroidal pyrazines were evaluated in the National Cancer Institute's new in vitro, disease-oriented antitumor screen, but none showed sufficient activity to warrant in vivo investigation.

  DOI：

  10.1021/jo00101a052

文献信息

• Transformations of solasodine and derivatives of hecogenin by Cunninghamella elegans
  作者：Asmita V. Patel、Gerald Blunden、Trevor A. Crabb

  DOI：10.1016/s0031-9422(00)90520-x

  日期：1993.12

  12-trione. When the (22 R ,25 R )-spirosolane, solasod-5-en-3β-ol (solasodine) was incubated with C. elegans , solasod-5-ene-3β,7β-diol, solasod-5-ene-3β,7α-diol and 3β-hydroxysolasod-5-en-7-one were produced. In contrast, incubation of solasodine with Penicillium patulum gave solasod-4-en-3-one and the 6-methylsalicylic acid salt of solasodine.

  摘要 (25 R )-5α-spirostan-3β,12β-diol (rockogenin) 与真菌 Cunninghamella elegans 孵育导致形成 (25 R )-7β,12β-dihydroxy-5α-spirostan-3-one，（ 25 R )-5α-spirostan-3β,7β,12β-三醇和 (25 R )-5α-spirostan-3β,7α,12β-三醇。(25 R )-5α-spirostan-3,12-dione (hecogenone) 与相同的真菌一起孵育产生 (25 R )-5α-spirostan-3,7,12-trione。当 (22 R ,25 R )-spirosolane、solaso​​d-5-en-3β-ol (solaso​​dine) 与秀丽隐杆线虫、solaso​​d-5-ene-3β,7β-diol、solaso​​d-5-ene-3β
• Production process for 16-dehydropregnenoneol and its analogs
  申请人：Tian Weisheng

  公开号：US20060166955A1

  公开（公告）日：2006-07-27

  The present invention relates to a clean process for the degradation of steroidal sapogenin to produce 16-dehydropregnenolone and its analogs. The pure or the crude pseudo steroidal sapogenin, derived from steroidal sapogenin, dissolved in organic solvent, reacts with hydrogen peroxide with or without metal compound and acid as catalyst, and the crude products directly go through elimination and hydrolization in the presence of base to give 16-Dehydropregnenolone or its analog, accompanied with the other product 4R(or S)-methyl-5-hydroxy-pentate, which is converted to 4R(or S)-methyl-δ-pentyl lactone after acidification and extraction from the water layer. This technology improved the utilizing degree of steroidal sapogenin, improved the yield, and cleared up the chromium pollution in the former technique. In a word, the method disclosed in this invention is more suitable for manufacture.

  本发明涉及一种用于降解类固醇皂甙生成16-去氢孕酮和其类似物的清洁工艺。从类固醇皂甙中提取的纯或粗假类固醇皂甙，溶解在有机溶剂中，与过氧化氢反应，可以加入金属化合物和酸作为催化剂，粗产品直接在碱的存在下经过消除和水解，得到16-去氢孕酮或其类似物，伴随另一产品4R（或S）-甲基-5-羟基-戊酸酯，经过酸化和从水层中提取后转化为4R（或S）-甲基-δ-戊内酯。这种技术提高了类固醇皂甙的利用率，提高了产量，并清除了以前技术中的铬污染。总之，本发明揭示的方法更适合生产。
• A Practical Synthesis of Cephalostatin 1
  作者：Yong Shi、Lanqi Jia、Qing Xiao、Quan Lan、Xiaohu Tang、Dahai Wang、Min Li、Yu Ji、Tao Zhou、Weisheng Tian

  DOI：10.1002/asia.201000882

  日期：2011.3.1

  Let′s get practical: A new practical synthetic strategy for natural sterols starting from pregnan‐(16S,20S)‐diols and steroid‐(16S),22‐lactones is presented. A tandem double oxymercuration–demercuration and a substitution–ketalization cascade are considered as the key reactions for the construction of the spiroketal rings.

  让我们付诸实践：从pregnan-（16 S，20 S）-二醇和类固醇（16 S），22-内酯开始，提出一种新的天然甾醇实用合成策略。串联双氧汞化-脱汞和取代-缩酮化级联被认为是构建螺环的关键反应。
• Steroidal glycosides for treating hypercholesterolemia
  申请人：Pfizer Inc.

  公开号：US05629295A1

  公开（公告）日：1997-05-13

  The application discloses steroidal glycoside compounds, especially spirostanyl glycosides, which have a glycosyl group O-linked to the C-3 hydroxy radical of the steroid and where the moieties at the C-10 and C-11 positions of the steroid are the same or different and are selected from the group consisiting of methylene, hydroxy and carbonyl. These steroid glycosides are useful as hypocholesterolemic agents and anti-atherosclerosis agents.

  本申请公开了类固醇糖苷化合物，特别是螺环甾体糖苷化合物，其具有糖基O-连接到类固醇的C-3羟基基团，其中类固醇的C-10和C-11位置的基团相同或不同，并且被选择自甲基，羟基和羰基的组成的群体。这些类固醇糖苷化合物可用作降低胆固醇和抗动脉粥样硬化剂。
• MODULATORS OF RETINOID-RELATED ORPHAN RECEPTOR GAMMA
  申请人：Orphagen Pharmaceuticals

  公开号：US20130150333A1

  公开（公告）日：2013-06-13

  Methods for modulating (inhibiting or stimulating) retinoid-related orphan receptor γ (RORγ) activity. This modulation has numerous effects, including inhibition of T H -17 cell function and/or T H -17 cell activity, and inhibition of re-stimulation of T H -17 cells, which are beneficial to treatment of inflammation and autoimmune disorders. Stimulation of RORγ results in stimulation of T H -17 cell function and/or activity which is beneficial for immune-enhancing compositions (e.g., vaccines).

  调节（抑制或刺激）视黄醇相关孤儿受体γ（RORγ）活性的方法。这种调节具有许多效果，包括抑制TH-17细胞功能和/或TH-17细胞活性，以及抑制TH-17细胞再激活，这对治疗炎症和自身免疫性疾病有益。刺激RORγ会导致TH-17细胞功能和/或活性的刺激，这对于免疫增强组合物（例如疫苗）有益。