(11β)-11-(Hydroxy)-9-fluoro-17-(methylthio)androsta-1,4,16-trien-3-one | 68159-86-4

• 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: (11β)-11-(Hydroxy)-9-fluoro-17-(methylthio)androsta-1,4,16-trien-3-one
• 英文别名: 9-fluoro-11β-hydroxy-17-(methylthio)androsta-1,4,16-trien-3-one；9-fluoro-11β-hydroxy-17-(methylthio)androsta-1,4,16-triene-3-one；9-Fluoro-11beta-hydroxy-17-(methylthio)androsta-1,4,16-trien-3-one；(8S,9R,10S,11S,13S,14S)-9-fluoro-11-hydroxy-10,13-dimethyl-17-methylsulfanyl-7,8,11,12,14,15-hexahydro-6H-cyclopenta[a]phenanthren-3-one
• CAS: 68159-86-4
• 化学式: C₂₀H₂₅FO₂S
• 分子量: 348.482
• InChiKey: PHJLTOYISIJECX-GJCUDGATSA-N

物化性质

• 沸点：
  498.7±45.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (11β)-11-(Hydroxy)-9-fluoro-17-(methylthio)androsta-1,4,16-trien-3-one 在 sodium acetate 、 乙酸酐 、 间氯过氧苯甲酸 作用下， 以 hexane chloroform 、 氯仿 为溶剂， 生成 17-[[(Acetyloxy)methyl]thio]-9-fluoro-11β-hydroxyandrosta-1,4,16-trien-3-one
  参考文献：
  名称：

  17-Alkylthio (and arylthio)

  摘要：

  具有以下结构式的类固醇化合物可以用作抗炎剂：##STR1## 其中X为--S--，##STR2## R.sub.1为烷基、芳基或酰氧基烷基；R.sub.2基团为卤素；R.sub.3为氢或卤素；R.sub.4为羰基、β-羟甲基亚甲基或β-酰氧甲基亚甲基；R.sub.5为氢或氟。

  公开号：

  US04094840A1
• 作为产物：
  描述：

  (11β)-9-Fluoro-11-hydroxy-17,17-bis(methylthio)androsta-1,4-dien-3-one 在 ice 作用下， 以 邻二乙苯 为溶剂， 生成 (11β)-11-(Hydroxy)-9-fluoro-17-(methylthio)androsta-1,4,16-trien-3-one
  参考文献：
  名称：

  17-Alkylthio (and arylthio)

  摘要：

  具有以下化学式的类固醇可以用作抗炎剂：##STR1## 其中X为--S--, ##STR2## R.sub.1为烷基，芳基或酰氧基烷基; R.sub.2基团为卤素; R.sub.3为氢或卤素; R.sub.4为羰基，.beta.-羟甲基或.beta.-酰氧甲基; R.sub.5为氢或氟。

  公开号：

  US04094840A1

文献信息

• 17-(Substituted thio)androst-4-ene[16,17,-b]-[1,4]benzodioxin-3-ones
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04265815A1

  公开（公告）日：1981-05-05

  Steroids having the formula ##STR1## are useful intermediates for the preparation of novel antiinflammatory agents having the formula ##STR2## In the above formulas, X is S, ##STR3## R.sub.1 is alkyl, aryl, arylalkyl or acyloxyalkyl; R.sub.2 is fluoro, chloro, bromo or iodo (all R.sub.2 groups are the same); R.sub.3 is hydrogen, fluoro, chloro, bromo or iodo; R.sub.4 is carbonyl, or .beta.-hydroxymethylene; R.sub.5 is hydrogen, methyl or fluorine; and R.sub.6 is chloro, bromo, alkoxy, aryloxy, alkylthio, or arylthio.

  具有以下结构式的类固醇是制备具有以下结构式的新型抗炎药物的有用中间体：在上述结构式中，X为S，R.sub.1为烷基、芳基、芳基烷基或酰氧烷基；R.sub.2为氟、氯、溴或碘（所有R.sub.2基团相同）；R.sub.3为氢、氟、氯、溴或碘；R.sub.4为羰基或β-羟甲基；R.sub.5为氢、甲基或氟；R.sub.6为氯、溴、烷氧基、芳氧基、烷硫氧基或芳硫氧基。
• Selective thioketalization process, process for preparing thioenol ethers from thioketals, and process for the preparation of thioketals
  申请人：E.R. SQUIBB & SONS, INC.

  公开号：EP0524813A1

  公开（公告）日：1993-01-27

  A selective thioketalization process for the preparation of a thioketal from a dione where one, but not the other, keto group of the dione is α,β-unsaturated, and where selective thioketalization occurs at the keto group of the dione which is not α,β-unsaturated, comprising the step of contacting the dione with a thiol, in the presence of a protic acid catalyst which is a complex of a Lewis acid and a protic source, wherein the temperature of the reaction medium is maintained below about 25°C during the reaction. Preferably, further, (i) the acid catalyst is employed in excess and/or (ii) the thiol is employed in excess. The inventive process may be employed, for example, in the preparation of a 3-keto,17-thioketalandrostene from the corresponding 3,17-diketoandrostene. A process for the preparation of thioenolethers from thioketals, especially 3-keto,17-thioenoletherandrostenes from 3-keto,17-thioketalandrostenes, wherein the thioketal is contacted with a protic acid catalyst. A process for the preparation of thioketals, especially mixed thioketals such as mixed 3-keto,17-thioketalandrostenes, from thioenolethers, comprising the step of contacting a thioenolether with a thiol in the presence of a protic acid catalyst.

  一种选择性硫醚化过程，用于从二酮制备硫醚，其中二酮的一个但不是另一个酮基是α，β-不饱和的，选择性硫醚化发生在不是α，β-不饱和的酮基上，包括将二酮与硫醇接触，在存在Lewis酸和质子源的复合物的质子酸催化剂的情况下，反应介质的温度在反应过程中保持在大约25°C以下。最好，进一步，(i) 过量使用酸催化剂和/或 (ii) 过量使用硫醇。该创新过程可以用于从相应的3,17-二酮雄烯制备3-酮，17-硫醚雄烯。一种从硫醚制备硫烯醚的过程，特别是从3-酮，17-硫醚雄烯制备3-酮，17-硫烯醚雄烯的过程，其中硫醚与质子酸催化剂接触。一种从硫烯醚制备硫醚的过程，特别是从硫烯醚制备混合硫醚，例如混合的3-酮，17-硫醚雄烯，包括将硫烯醚与硫醇在质子酸催化剂的存在下接触的步骤。
• 13-Alkylthio (and arylthio)-11,17-epoxy-17-methyl-18-norandrostenes
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04133811A1

  公开（公告）日：1979-01-09

  Steroids having the formula ##STR1## wherein X is --S--, ##STR2## R.sub.1 is alkyl or aryl; R.sub.2 is hydrogen or halogen; and R.sub.3 is hydrogen, fluorine or methyl; can be used as antiinflammatory agents.

  具有以下式子的类固醇可以用作抗炎药物：##STR1## 其中X为--S--, ##STR2## R.sub.1为烷基或芳基；R.sub.2为氢或卤素；R.sub.3为氢、氟或甲基。
• 17-Alkylthio (and arylthio)-1',2',3',4'-tetrahydroandrosteno [16
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04091036A1

  公开（公告）日：1978-05-23

  pg,1 Steroids having the formula ##STR1## wherein X is ##STR2## R.sub.1 is alkyl, aryl or acyloxyalkyl; R.sub.2 and R.sub.3 are the same or different and are hydrogen, alkyl, alkoxy, carboalkoxy, formyl, ##STR3## hydroxy, halogen, phenyl or cyano, with the proviso that when R.sub.2 and R.sub.3 are different, one of R.sub.2 and R.sub.3 is hydrogen; R.sub.4 is carbonyl, .beta.-hydroxymethylene or .beta.-acyloxymethylene; R.sub.5 is hydrogen or halogen; and R.sub.6 is hydrogen or fluorine; can be used as antiinflammatory agents.

  具有以下式子的类固醇化合物可以用作抗炎药物：##STR1## 其中，X为##STR2## R.sub.1为烷基、芳基或酰氧基烷基；R.sub.2和R.sub.3相同或不同，可以是氢、烷基、烷氧基、羧烷氧基、甲酰基、##STR3## 羟基、卤素、苯基或氰基，但R.sub.2和R.sub.3不同时，其中一个为氢；R.sub.4为羰基、β-羟甲基或β-酰氧甲基；R.sub.5为氢或卤素；R.sub.6为氢或氟。
• Intermediates useful in the preparation of 17,17-bis(substituted
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04435326A1

  公开（公告）日：1984-03-06

  Androstenes having the formula ##STR1## wherein R.sub.1 hydrogen and R.sub.2 is alkyl, cycloalkyl, aryl, arylalkyl, alkylthioalkyl, alkoxyalkyl, alkanoyloxyalkyl, aroyloxyalkyl, alkoxycarobnylalkyl, carboxyalkyl, or arylalkyl, or R.sub.1 is alkanoyl or aroyl and R.sub.2 is alkyl; R.sub.3 is hydrogen, hydroxy, alkoxy, aryloxy, oxo, methylene, alkylthio, arylthio, alkanoyl, alkanoyloxy, or halogen; R.sub.4 is carbonyl, .beta.-hydroxymethylene or .beta.-acetyloxymethylene; R.sub.5 is hydrogen or halogen; and R.sub.6 is hydrogen, methyl, hydroxy, alkanoyl or halogen are useful intermediates for the preparation of steroids having antiinflammatory activity.

  AndroSTenes具有以下结构式##STR1## 其中R.sub.1为氢，R.sub.2为烷基、环烷基、芳基、芳基烷基、烷基硫醇烷基、烷氧基烷基、烷酰氧基烷基、芳酰氧基烷基、烷氧羰基烷基、羧基烷基或芳基烷基，或者R.sub.1为烷酰基或芳酰基，R.sub.2为烷基；R.sub.3为氢、羟基、烷氧基、芳氧基、氧代、亚甲基、烷硫基、芳硫基、烷酰基、烷酰氧基或卤素；R.sub.4为羰基、β-羟甲基或β-乙酰氧甲基；R.sub.5为氢或卤素；R.sub.6为氢、甲基、羟基、烷酰基或卤素。这些化合物是制备具有抗炎活性的类固醇的有用中间体。