17,21-dihydroxy-6α-fluoro-16β-methylpregna-1,4,9(11)-triene-3,20-dione 17,21-diacetate | 50630-16-5

• 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: 17,21-dihydroxy-6α-fluoro-16β-methylpregna-1,4,9(11)-triene-3,20-dione 17,21-diacetate
• 英文别名: 6α-fluoro-17α,21-dihydroxy-16β-methylpregna-1,4,9(11)-triene-3,20-dione 17,21-diacetate；6α-fluoro-16β-methyl-17α,21-diacetoxypregna-1,4,9(11)-triene-3,20-dione；6alpha-Fluoro-16beta-methyl-17alpha,21-diacetoxypregna-1,4,9(11)-triene-3,20-dione；[2-[(6S,8S,10R,13S,14S,16S,17R)-17-acetyloxy-6-fluoro-10,13,16-trimethyl-3-oxo-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate
• CAS: 50630-16-5
• 化学式: C₂₆H₃₁FO₆
• 分子量: 458.527
• InChiKey: JNTXVYUQFYREAY-QGKCFBNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  86.7
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  17,21-dihydroxy-6α-fluoro-16β-methylpregna-1,4,9(11)-triene-3,20-dione 17,21-diacetate 在 氯 、 potassium carbonate 、 过碘酸 作用下， 以 吡啶 、 甲醇 、 四氯化碳 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.75h， 生成
  参考文献：
  名称：

  Thiol esters from steroid 17.beta.-carboxylic acids: carboxylate activation and internal participation by 17.alpha.-acylates

  摘要：

  DOI：

  10.1021/jo00362a028
• 作为产物：
  描述：

  6α-fluoro-16β-methyl-17α,21-diacetoxypregna-4,9(11)-diene-3,20-dione 、 在 丙酮 、 alumina 作用下， 以 1,4-二氧六环 为溶剂， 反应 10.0h， 以to yield 6α-fluoro-16β-methyl-17α,21-diacetoxypregna-1,4,9(11)-triene-3,20-dione which的产率得到17,21-dihydroxy-6α-fluoro-16β-methylpregna-1,4,9(11)-triene-3,20-dione 17,21-diacetate
  参考文献：
  名称：

  4-Halo steroids

  摘要：

  某些4-氟或4-氯取代的孕酮-4-烯-3,20-二酮或孕酮-1,4-烯-3,20-二酮可用作局部抗炎类固醇。这些化合物在9α位取代为氢、氟、氯或溴；在6α位取代为氢、氟或氯；在11位取代为酮、β-羟基或β-氯（只有在存在9α-氯时才有后者）；在16α、17α位取代为异丙亚甲基二氧基或在17α位为羟基（或酯）时在16α位（或16β位）取代为甲基；在21位取代为2-6个碳的单氟、氯、溴、羟基或脂肪酰氧基或二氟、二氯、二羟基或二甲氧基。

  公开号：

  US04273770A1

文献信息

• 17.beta.-thiocarboxylic acid esters of
  申请人：Syntex (U.S.A.) Inc.

  公开号：US04261984A1

  公开（公告）日：1981-04-14

  Certain 3-oxoandrost-4-ene and 3-oxoandrosta-1,4-diene 17.beta.-thiocarboxylic acid esters substituted at the 4-position with a fluoro or chloro, optionally substituted at the 6- position with fluoro or chloro and at 16.beta. with methyl are useful as anti-inflammatory steroids. These compounds are optionally substituted at the 9.alpha. position with fluoro, chloro or bromo; substituted at the 11 with a keto, a beta-hydroxy or a beta-chloro (the latter only when there is a 9.alpha.-chloro); when there is a 17.alpha.-hydroxy (or an ester).

  在4-位置用氟或氯取代的某些3-氧代雄甾-4-烯和3-氧代雄甾-1,4-二烯17.beta.-硫代羧酸酯，可选择在6-位置用氟或氯取代，在16.beta.位置用甲基取代，可用作抗炎类固醇。这些化合物可选择在9.alpha.位置用氟、氯或溴取代；在11位置用酮、β-羟基或β-氯代替（只有在有9.alpha.-氯时才有后者）；当有17.alpha.-羟基（或酯）时。
• 3-Oxo-4-halo-16.beta.-methylandrost-4-ene 17.beta.-carboxylic acids and
  申请人：Syntex (U.S.A.) Inc.

  公开号：US04278669A1

  公开（公告）日：1981-07-14

  Certain 3-oxoandrost-4-ene and 3-oxoandrosta-1,4-diene 17.beta.-carboxylic acids (and esters thereof) substituted at the 4-position with a fluoro or chloro, optionally substituted at the 6- position with fluoro or chloro and at 16.beta. with methyl are useful as anti-inflammatory steroids. These compounds are optionally substituted at the 9.alpha. position with fluoro, chloro or bromo; substituted at the 11 with a keto, a beta-hydroxy or a beta-chloro (the latter only when there is a 9.alpha.-chloro); when there is a 17.alpha.-hydroxy (or an ester).

  在4位取代有氟或氯，6位和16.beta.取代有甲基的某些3-氧代雄甾-4-烯和3-氧代雄甾-1,4-二烯-17.beta.-羧酸（及其酯）可用作抗炎类固醇。这些化合物在9.alpha.位置可选地取代有氟、氯或溴；在11位取代有酮基、β-羟基或β-氯基（只有在有9.alpha.-氯基时才有后者）；当存在17.alpha.-羟基（或酯）时。
• 17-Beta-thiocarboxylic acid esters of 4-halo-3-oxoandrost-4-enes, their pharmaceutical use and processes for their preparation
  申请人：SYNTEX (U.S.A.) INC.

  公开号：EP0004773A2

  公开（公告）日：1979-10-17

  17β-Thiocarboxylic acid esters of 4-halo-3-oxoandrost-4- enes of the formula: wherein X' is fluoro, chloro or bromo; X2 is fluoro, chloro or hydrogen; X3 is fluoro, chloro, bromo or hydrogen; X4 is =C=O or or may also be when X3 is chloro; R is alkyl or 1 to 6 carbon atoms or phenyl or benzyl optionally substituted with one substituent on the phenyl ring chosen from the group consisting of alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms and halo; R1 is hydrogen or alkanoyl of 2 to 6 carbon atoms when R2 is hydrogen, a-methyl or β-methyl, or OR' and R2 together are isopropylidenedioxy; and the solid and broken lines between C-1 and C-2 represent a double or a single bond; are useful as anti-inflammatory agents. They can be prepared by treating the corresponding 17β-carboxylic acid with a suitable base salt of RSH. The 17β-hydroxy compounds can be esterified to produce the 17β-alkanoyloxy compound. The double bond at the 4,5 position can be produced by contacting the corresponding Δ5 compound with a base.

  17β-Thiocarboxylic acid esters of 4-halo-3-oxoandrost-4- enes of the formula： 其中 X' 是氟、氯或溴； X2 是氟、氯或氢 X3 是氟、氯、溴或氢； X4 是 =C=O 或 或也可以是 当 X3 为氯时； R 是 1 至 6 个碳原子的烷基或苯基或苄基，可选择被苯基环上的一个取代基取代，该取代基可从 1 至 4 个碳原子的烷基、1 至 4 个碳原子的烷氧基和卤素组成的组中选择； 当 R2 为氢、a-甲基或 β-甲基时，R1 为氢或 2 至 6 个碳原子的烷酰基，或 OR' 和 R2 合在一起为异亚丙基二氧基；以及 C-1 和 C-2 之间的实线和断线代表双键或单键； 可用作抗炎剂。它们可以通过将相应的 17β- 羧酸与合适的 RSH 碱盐进行处理来制备。17β-hydroxy 化合物经酯化后可生成 17β-alkanoyloxy 化合物。4,5 位的双键可通过将相应的 Δ5 化合物与碱接触而生成。
• 16-methylene-steroids and their preparation
  申请人：THE UPJOHN COMPANY

  公开号：EP0104054A2

  公开（公告）日：1984-03-28

  16-Methylene-17-keto-steroids are transformed to the corresponding 16-methylene-17a-hydroxyprogesterones which are intermediates useful in the production of betamethasone, diflorasone diacetate and melengesterol acetate. 17a-Hydroxy-6, 16-dimethylene-pregn-4-ene-3, 20-dione is simultaneously isomerized and acylated to 17a-hydroxy-6-methyl-16-methylenepregna-4, 6-diene-3, 20-dione 17-acetate.

  16-亚甲基-17-酮类类固醇可转化为相应的 16-亚甲基-17a-羟基黄体酮，这些黄体酮是生产倍他米松、双醋酸地氟松和醋酸美伦孕酮的中间体。17a-羟基-6，16-二亚甲基孕甾-4-烯-3，20-二酮同时异构化和酰化为 17a-羟基-6-甲基-16-亚甲基孕甾-4，6-二烯-3，20-二酮 17-乙酸酯。
• 17-Alpha ethynyl steroids
  申请人：THE UPJOHN COMPANY

  公开号：EP0402963A2

  公开（公告）日：1990-12-19

  A 17α-ethynyl steroid selected from the group consisting of 17α-­ethynyl-3,17β-dihydroxy-16β-methylandrosta-3,5-diene 3-methyl ether, 17α-ethynyl-3,17β-dihydroxy-16β-methylandrost-5-ene 3-THP ether, 17α-­ethynyl-3,17β-dihydroxy-16β-methylandrosta-3,5,9(11)-triene 3-methyl ether, 17α-ethynyl-17β-hydroxy-16β-methylandrost-4-en-3-one, 17α-­ethynyl-17β-hydroxy-16β-methylandrosta-4,9(11)-dien-3-one, and 17α-­ethynyl-17β-hydroxy-16β-methylandrosta-1,4,9(11)-trien-3-one.

  一种 17α-乙炔类固醇，选自以下组别：17α-乙炔基-3,17β-二羟基-16β-甲基雄甾-3,5-二烯 3-甲醚、17α-乙炔基-3,17β-二羟基-16β-甲基雄甾-5-烯 3-THP醚、17α-乙炔基-3,17β-二羟基-16β-甲基雄甾-3、5,9(11)-triene 3-methyl ether, 17α-ethynyl-17β-hydroxy-16β-methylandrost-4-en-3-one, 17α-­ethynyl-17β-hydroxy-16β-methylandrosta-4,9(11)-dien-3-one, and 17α-­ethynyl-17β-hydroxy-16β-methylandrosta-1,4,9(11)-trien-3-one.