(6S,16R,17R)-6-氟-11,17-二羟基-17-(2-羟基乙酰基)-10,13,16-三甲基-2,6,7,8,9,11,12,14,15,16-十氢-1H-环戊二烯并[a]菲-3-酮 | 387-59-7

• 中文名称: (6S,16R,17R)-6-氟-11,17-二羟基-17-(2-羟基乙酰基)-10,13,16-三甲基-2,6,7,8,9,11,12,14,15,16-十氢-1H-环戊二烯并[a]菲-3-酮
• 英文名称: 6α-fluoro-11β,17,21-trihydroxy-16α-methyl-pregn-4-ene-3,20-dione
• 英文别名: 6α-Fluor-11β,17,21-trihydroxy-16α-methyl-pregn-4-en-3,20-dion；6α-fluoro-16α-methyl-cortisol；6α-Fluoro-11β,17α,21-trihydroxy-16α-methylpregn-4-ene-3,20-dione；6alpha-Fluoro-11beta,17,21-trihydroxy-16alpha-methylpregn-4-ene-3,20-dione；(6S,8S,9S,10R,11S,13S,14S,16R,17R)-6-fluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
• CAS: 387-59-7
• 化学式: C₂₂H₃₁FO₅
• 分子量: 394.484
• InChiKey: JXOONFORBFAKIN-AFYJWTTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  94.8
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (6S,16R,17R)-6-氟-11,17-二羟基-17-(2-羟基乙酰基)-10,13,16-三甲基-2,6,7,8,9,11,12,14,15,16-十氢-1H-环戊二烯并[a]菲-3-酮 生成 21-acetoxy-6α-fluoro-11β,17-dihydroxy-16α-methyl-pregn-4-ene-3,20-dione
  参考文献：
  名称：

  Karady; Sletzinger, Chemistry and industry, 1959, p. 1159

  摘要：

  DOI：
• 作为产物：
  描述：

  (20Ξ)-3,3-ethanediyldioxy-6β-fluoro-16α-methyl-17,20;20,21-bis-methylenedioxy-5α-pregnane-5,11β-diol 在 甲酸 、 硫酸 、 sodium methylate 作用下， 生成 (6S,16R,17R)-6-氟-11,17-二羟基-17-(2-羟基乙酰基)-10,13,16-三甲基-2,6,7,8,9,11,12,14,15,16-十氢-1H-环戊二烯并[a]菲-3-酮
  参考文献：
  名称：

  Karady; Sletzinger, Chemistry and industry, 1959, p. 1159

  摘要：

  DOI：

文献信息

• 4-Halo steroids
  申请人：Syntex (U.S.A.) Inc.

  公开号：US04273770A1

  公开（公告）日：1981-06-16

  Certain pregn-4-ene-3,20-diones or pregn-1,4-diene-3,20-diones 4-substituted with a fluoro or chloro are useful as topical anti-inflammatory steroids. These compounds are substituted at 9.alpha. with hydrogen, fluoro, chloro or bromo; at 6.alpha. with hydrogen, fluoro or chloro; at the 11 position with a keto, a .beta.-hydroxy or a .beta.-chloro (the latter only when there is a 9.alpha.-chloro); at 16.alpha., 17.alpha.-positions with isopropylidenedioxy or at 16.alpha.- (or 16.beta.) with methyl when 17.alpha. is hydroxy (or an ester); and at the 21-position with mono-fluoro, chloro, bromo, hydroxy or alkanoyloxy of 2-6 carbons or difluoro, dichloro, dihydroxy or dimethoxy.

  某些带有氟或氯基的孕烯酮或孕烯二酮在局部抗炎类固醇中具有用途。这些化合物在9.alpha.位置被氢、氟、氯或溴取代；在6.alpha.位置被氢、氟或氯取代；在11位点被酮基、β-羟基或β-氯基（仅当存在9.alpha.-氯基时）取代；在16.alpha.、17.alpha.位置被异丙亚甲二氧基取代，或在16.alpha.（或16.beta.）位置被甲基取代，当17.alpha.为羟基（或酯）时；在21位点被2-6碳的单氟、氯、溴、羟基或烷酰氧基，或二氟、二氯、二羟基或二甲氧基取代。
• 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。
• 6α-FLUORO-16α-METHYL ANALOGS OF CORTICAL HORMONES
  作者：William P. Schneider、Frank H. Lincoln、George B. Spero、H. C. Murray、John L. Thompson

  DOI：10.1021/ja01521a088

  日期：1959.6
• Edwards et al., Proceedings of the Chemical Society, London, 1959, p. 87
  作者：Edwards et al.

  DOI：——

  日期：——
• US3956349A
  申请人：——

  公开号：US3956349A

  公开（公告）日：1976-05-11