21-methoxyprogesterone | 20380-14-7

• 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: 21-methoxyprogesterone
• 英文别名: 21-methoxy-pregn-4-ene-3,20-dione；21-Methoxy-pregn-4-en-3,20-dion；21-Methoxy-pregnen-(4)-dion-(3.20)；21-Methoxy-pregnen-(4)-dion-(3,20)；(8S,9S,10R,13S,14S,17S)-17-(2-methoxyacetyl)-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• CAS: 20380-14-7
• 化学式: C₂₂H₃₂O₃
• 分子量: 344.494
• InChiKey: ANBNZGCOSNPFBV-XUCMERPOSA-N

物化性质

• 熔点：
  161-165 °C
• 沸点：
  489.4±45.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  21-methoxyprogesterone 在 甲醇 、 碘代三甲硅烷 、 silver(l) oxide 作用下， 以 氯仿 、 乙腈 为溶剂， 反应 52.0h， 生成 黄体酮
  参考文献：
  名称：

  Efficient C-21 deoxygenation of 21-alkoxy-20-keto corticoid steroids with trimethylsilyl iodide in the presence of methanol

  摘要：

  Reaction of 21-alkyl ethers 1, 4-6, 8, and 9 with a large excess of trimethylsilyl iodide (TMSI) produced the deoxygenated products 3 and 11 in low to moderate yields along with a small amount of 21-alcohols 2 and 10. The deoxygenation reaction in the presence of 1.5 molar equiv of MeOH gave the products in much higher yields than those without MeOH, except the reaction of the ethyl and n-propyl ethers 4 and 5. Treatment of 1 and 8 with trimethylsilyl chloride/NaI in the presence of MeOH gave similar results to those with TMSI. Compound 3 was also produced in high yields by reaction of 1 and 4 with HI under mild conditions. On the other hand, treatment of 17-alpha-ketol 7 with TMSI in the presence of MeOH yielded 17-alpha-beta-methyl D-homo steroid 15. The results along with deuterium-labeling experiments with MeOD and IR and H-1 NMR spectral analysis during the reaction with TMSI suggest that dealkylation of the 21-alkyl ethers precedes the deoxygenation, in which HI produced in situ by reaction of MeOH with TMSI would be involved.

  DOI：

  10.1021/jo00001a062
• 作为产物：
  描述：

  methyl-[3β-hydroxy-24,24-diphenyl-cholatrien-(5,20(22)ξ,23)-yl-(21)]-ether 在 环己酮 、 aluminum isopropoxide 、 甲苯 作用下， 生成 21-methoxyprogesterone
  参考文献：
  名称：

  关于类固醇。（第67部分）。胆汁酸侧链IX的简单分解。的转换的δ 5 -3β氧基-胆烯酸成-11-脱氧皮质酮酯和醚

  摘要：

  DOI：

  10.1002/hlca.19470300519

文献信息

• 1,3,6-DIOXAZOCAN-2-ONES AND ANTIMICROBIAL CATIONIC POLYCARBONATES THEREFROM
  申请人：Agency for Science, Technology and Research

  公开号：US20150264932A1

  公开（公告）日：2015-09-24

  Eight-membered ring cyclic carbonates comprising a ring nitrogen at position 6 (1,3,6-dioxazocan-2-ones) were prepared by reaction of precursor diols with active carbonates. The ring nitrogen is linked to a pendant group Y′ via a methylene linking group. The cyclic carbonates undergo organocatalyzed ring opening polymerization to form an initial polycarbonate comprising a backbone tertiary amine group. Quaternization of the initial polycarbonates forms cationic polycarbonates comprising a positive-charged backbone quaternary nitrogen. The cationic polycarbonates can be potent antimicrobial agents.

  含有八元环的环状碳酸酯，其中在位置6处有一个环状氮原子（1,3,6-二氧杂环己烷-2-酮），通过前体二醇与活性碳酸酯的反应制备。环状氮原子通过一个亚甲基连接基团与一个挂链基团Y'相连。这些环状碳酸酯经有机催化的环开聚合反应形成初始聚碳酸酯，其中包含一个主链三级胺基团。对初始聚碳酸酯进行季铵化形成带有正电荷主链季铵氮的阳离子聚碳酸酯。这些阳离子聚碳酸酯可以是有效的抗菌剂。
• VITAMIN FUNCTIONALIZED GEL-FORMING BLOCK COPOLYMERS FOR BIOMEDICAL APPLICATIONS
  申请人：INTERNATIONAL BUSINESS MACHINES CORPORATION

  公开号：US20180117162A1

  公开（公告）日：2018-05-03

  Gel-forming block copolymers were prepared comprising i) a central hydrophilic block consisting essentially of a divalent poly(ethylene oxide) chain and ii) two peripheral monocarbonate or polycarbonate hydrophobic blocks linked to the central block by linking groups bearing one or more hydrogen bond forming *—N(H)—* groups. The hydrophobic blocks comprise one or more vitamin-bearing subunits. The gel-forming block copolymers can be used to prepare various biodegradable and/or biocompatible hydrogel and organogel drug compositions, in particular antimicrobial and/or anti-tumor drug compositions. The hydrogel compositions have utility in depot injections for drug delivery. The hydrogen bonding *—N(H)—* group(s) provide longer in vivo lifetime of the hydrogel before degradation and a more prolonged and controlled release rate of a hydrophobic drug compared to similar hydrogels prepared from poly(ethylene glycol).

  制备了包含以下组成部分的凝胶形成嵌段共聚物：i）主要由二价聚乙二醇链组成的中心亲水性块和ii）通过带有一个或多个氢键形成*—N(H)—*基团连接到中心块的两个外周单碳酸酯或多碳酸酯疏水性块。疏水性块包含一个或多个含维生素的亚单位。这些凝胶形成嵌段共聚物可用于制备各种可生物降解和/或生物相容的水凝胶和有机凝胶药物组合物，特别是抗微生物和/或抗肿瘤药物组合物。水凝胶组合物在药物输送的库存注射中具有实用性。与由聚乙二醇制备的类似水凝胶相比，氢键*—N(H)—*基团提供了凝胶在体内降解之前更长的生命周期，以及与水凝胶相比更延长和控制释放速率的疏水性药物。
• Über Steroide und Sexualhormone. 166. Mitteilung. Über Äther der Ketole vom Typus des Desoxy-corticosterons
  作者：H. Heusser、Ch. R. Engel、Pl. A. Plattner

  DOI：10.1002/hlca.19490320734

  日期：1949.12.1

  Bei der Einwirkung von Natriumphenolat in Aceton auf 21-Brom-20-keto-Steroide entstehen unter Erhaltung des Gerüstes Phenyläther der Ketole vom Typus des Desoxy-corticosterons. Die entsprechenden Methyläther sind aus 21-Diazo-20-keto-Verbindungen durch deren Reaktion mit Methanol-Kupferoxyd leicht zugänglich.

  北埃塞顿地区的北德尔·埃因维肯·冯·萘酚酚酯，通常在脱氧-皮质酮类植物中被捕到。甲基丙烯酸甲酯21-Diazo-20-keto-Verbindungen durch deren Reakation mit甲醇-Kupferoxyd leichtzugänglich。
• CYCLIC CARBONATE MONOMERS AND RING OPENED POLYCARBONATES THEREFROM
  申请人：International Business Machines Corporation

  公开号：US20160009860A1

  公开（公告）日：2016-01-14

  Eight-membered ring cyclic carbonates having an oxygen or an acylated nitrogen at position 6 were prepared by reaction of precursor diols with ethyl chloroformate. The cyclic carbonates undergo organocatalyzed ring opening polymerization. In one instance, the initial polymer formed comprises a carbonate repeat unit having a Boc-protected nitrogen in the polymer backbone. Deprotecting the nitrogen with acid forms a cationic carbonate repeat unit having a positive charged secondary ammonium nitrogen in the polymer backbone.

  通过前体二醇与乙酰氯甲酸酯反应制备了在6位具有氧或酰化氮的八元环环状碳酸酯。这些环状碳酸酯经过有机催化的开环聚合。在一个实例中，初始聚合物由具有Boc保护氮的碳酸酯重复单元组成。用酸去保护氮会形成带有正电荷的次级铵氮的阳离子碳酸酯重复单元在聚合物骨架中。
• A synthesis of 3.beta.-hydroxy-5.beta.,14.alpha.-bufa-20,22-dienolide from deoxycorticosterone
  作者：Philip E. Bauer、Keith S. Kyler、David S. Watt

  DOI：10.1021/jo00149a007

  日期：1983.1