17α-ethynyl-17β-trifluoroacetoxy-androst-4-en-3-one | 85639-42-5

• 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: 17α-ethynyl-17β-trifluoroacetoxy-androst-4-en-3-one
• 英文别名: (17α)-17-<(trifluoroacetyl)oxy>pregn-4-en-20-yn-3-one；17β-hydroxy-17α-pregn-4-en-20-yn-3-one trifluoroacetate；17α-ethynyl-17β-trifluoroacetoxy-4-androsten-3-one；(17α)-17-[(trifluoroacetyl)oxy]pregn-4-en-20-yn-3-one；[(8R,9S,10R,13S,14S,17R)-17-ethynyl-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-yl] 2,2,2-trifluoroacetate
• CAS: 85639-42-5
• 化学式: C₂₃H₂₇F₃O₃
• 分子量: 408.461
• InChiKey: JOFSVUNVTFNVBL-LHZXLZLDSA-N

物化性质

• 熔点：
  149-150 °C(Solv: cyclohexane (110-82-7))
• 沸点：
  450.5±45.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  17α-ethynyl-17β-trifluoroacetoxy-androst-4-en-3-one 在 N-溴代丁二酰亚胺(NBS) 、 silver nitrate 作用下， 以 丙酮 为溶剂， 反应 20.5h， 生成 21-Brom-17-(formyloxy)-4-pregnen-3,20-dion
  参考文献：
  名称：

  17α-（卤乙炔基）-17β-（硝基氧基）雄烯类化合物的皮质类化合物侧链的结构

  摘要：

  在室温下，将17α-（溴乙炔基）和17α-（氯乙炔基）-17β-（硝基氧基）-雄烯衍生物2c – f转化为甲酸/ N-甲基-2-吡咯化物中的21-卤素-17α- 。（甲酰氧基）-20-酮戊三醇3a-d um，通过17α-羟基化合物3a-h从中获得21-乙酰氧基-17α-羟基-20-酮3i和3j。-尽管与2c类似物17α-（溴乙炔基）-17β苯甲酸酯2k和2l不与银盐反应，但可以是17α-（溴乙炔基）-17β-三卤乙酸酯2m和2n在高温下进入21-溴17α-（甲酰氧基）-20-酮3a。副反应的产物2c3a和2M，N3A是Δ 13类固醇4。

  DOI：

  10.1002/jlac.198719870347
• 作为产物：
  描述：

  炔孕酮 生成 17α-ethynyl-17β-trifluoroacetoxy-androst-4-en-3-one
  参考文献：
  名称：

  CHRISTIANSEN, ROBERT G.;BELL, MALCOLM R.;DAMBRA, THOMAS E.;MALLAMO, JOHN +, J. MED. CHEM., 33,(1990) N, C. 2094-2100

  摘要：

  DOI：

文献信息

• Process for the preparation of 17-haloethynyl steroids, and novel
  申请人：Schering Aktiengesellschaft

  公开号：US04567002A1

  公开（公告）日：1986-01-28

  17-haloethynyl steroids of the partial formula ##STR1## wherein R.sub.1 is hydrogen or methyl, R.sub.2 is alkyl of 1-4 carbon atoms, acyl of 1-7 carbon atoms, trimethylsilyl, 2-tetrahydropyranyl, or nitrate, X is bromine or iodine, and V is methylene, ethylene, vinylene, ethylidene, vinylidene or cyclopropylene, can be prepared by treating an ethynyl steroid of the partial formula ##STR2## wherein R.sub.1, R.sub.2, and V are as defined above, in an inert solvent with a brominating agent or an iodinating agent in the presence of a silver salt. Certain new compounds are also provided.

  部分结构式为##STR1##的17-卤乙炔基类固醇，其中R.sub.1为氢或甲基，R.sub.2为1-4个碳原子的烷基，1-7个碳原子的酰基，三甲基硅基，2-四氢吡喃基或硝酸酯基，X为溴或碘，V为亚甲基，乙烯基，乙烯基，乙基亚甲基，乙烯亚甲基或环丙基，可以通过在惰性溶剂中用溴化剂或碘化剂处理部分结构式为##STR2##的乙炔基类固醇来制备，其中R.sub.1，R.sub.2和V如上定义，在存在银盐的情况下。还提供了某些新化合物。
• Steroids 49. Investigations on the dehydration of 17α-ethynl-17β- hydroxysteroids
  作者：Irén Vincze、Magdalena L″okös、Tamás Bakos、Anna Dancsi、Marianna Mák

  DOI：10.1016/0039-128x(93)90022-f

  日期：1993.5

  The acidic dehydration of 17alpha-ethynyl-17beta-hydroxysteroids (1-3) was investigated. On reaction with thionyl chloride, phosphorus oxychloride, and formic acid, the desired dehydration was accompanied by chlorination, Wagner-Meerwein rearrangement, and D-homoaromatic rearrangement. The structure of the product from the transformation of 17beta-hydroxypregn-20-yne derivative (3) on reaction with formic acid was misjudged. It was regarded as a pregn-16-en-20-yne (10) instead of the actually rearranged D-homoaromatic compound (11). As a consequence, physical data corresponding to this latter structure have been cited in the literature as those of pregn-16-en-20-yne derivative (10). This confusion prompted us to prepare compounds of both types (4, 9, 10, and 11), the characterization of which is here described.
• Antiandrogenic steroidal sulfonylpyrazoles
  作者：Robert G. Christiansen、Malcolm R. Bell、Thomas E. D'Ambra、John P. Mallamo、John L. Herrmann、James H. Ackerman、Chester J. Opalka、Rudolph K. Kullnig、Richard C. Winneker

  DOI：10.1021/jm00170a008

  日期：1990.8

  The steroidal sulfonylpyrazole 1 bound to the rat ventral prostate androgen receptor in vitro; it inhibited testosterone propionate induced increases in ventral prostate weight in vivo in the castrated, immature male rat with an ED50 of 15 mg/kg po. Compound 1 lacked androgenic activity in vivo in contrast to the parent steroidal pyrazole 5, which was both androgenic and antiandrogenic. The 2'- and 5'-methylsulfonyl isomers 6 and 6a did not bind to the androgen receptor. Introduction of an alkylsulfonyl at the N-1'-position has served, therefore, to isolate the intrinsic antiandrogenic properties of the steroidal heterocycle free of apparent hormone agonist properties. Structure-activity relationship studies revealed that a methylsulfonyl group at N-1' together with a C-17 alpha-substituent were the optimal combination for in vitro androgen receptor binding, in vivo antiandrogenic potency, and a lack of androgenic activity.
• HOFMEISTER, H.;LAURENT, H.;ANNEN, K.;WIECHERT, R.
  作者：HOFMEISTER, H.、LAURENT, H.、ANNEN, K.、WIECHERT, R.

  DOI：——

  日期：——
• ——
  作者：BOOR LAJOSNE、 TOTH J.、 HOLLY S.、 SZEN T.、 GABOR L.、 MAJOR OTTONE

  DOI：——

  日期：——