11β-<4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>phenyl>-3,3-<1,2-ethanediylbis(oxy)>-estr-4-en-17-one | 156352-58-8

• 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-<4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>phenyl>-3,3-<1,2-ethanediylbis(oxy)>-estr-4-en-17-one
• 英文别名: 11β-[4-[[Dimethyl(1,1-dimethylethyl)silyl]oxy]phenyl]-3,3 [1,2-ethanediylbis(oxy)]estr-5-en-17-one；11β-[4-[[dimethyl-(1,1-dimethylethyl)silyl]oxy]phenyl]-3,3-[1,2-ethanediylbis(oxy)]oestr-5-en-17-one；(8R,9S,10R,11S,13S,14S)-11-[4-[tert-butyl(dimethyl)silyl]oxyphenyl]-13-methylspiro[1,2,4,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-3,2'-1,3-dioxolane]-17-one
• CAS: 156352-58-8
• 化学式: C₃₂H₄₆O₄Si
• 分子量: 522.8
• InChiKey: CWQUHLAZZUGXEL-DFKRMGCYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.65
• 重原子数：
  37
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  11β-<4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>phenyl>-3,3-<1,2-ethanediylbis(oxy)>-estr-4-en-17-one 在 lithium aluminium tetrahydride 、 3-硝基-2,2,2-三氟苯乙酮 、 双氧水 、 碳酸氢钠 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 121.0h， 生成 11β-<4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>phenyl>-3,3-<1,2-ethanediylbis(oxy)>-5α-estrane-5,17β-diol
  参考文献：
  名称：

  Synthesis and biological activity of 17-chloro-16(17) unsaturated D-homo antiprogestins

  摘要：

  An efficient approach to 17-chloro-16(17) unsaturated D-homo antiprogestins is described. The key steps of the synthesis are a ring-expansion via dichlorocarbene addition to a 17-silyl enol ether and a palladium catalyzed coupling of an 11 beta-(4-aryltriflate) with tributyl(1-ethoxyethenyl)stannane or diethyl(3-pyridinyl)borane. The new progestelone antagonists were tested for their biological activities and compared to those of known antiprogestins.

  DOI：

  10.1016/0039-128x(94)90024-8
• 作为产物：
  描述：

  3,3-<1,2-ethanediylbis(oxy)>-11β-(4-methoxyphenyl)estr-4-en-17-one 在 咪唑 、 mesna 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 11β-<4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>phenyl>-3,3-<1,2-ethanediylbis(oxy)>-estr-4-en-17-one
  参考文献：
  名称：

  Synthesis and biological activity of 17-chloro-16(17) unsaturated D-homo antiprogestins

  摘要：

  An efficient approach to 17-chloro-16(17) unsaturated D-homo antiprogestins is described. The key steps of the synthesis are a ring-expansion via dichlorocarbene addition to a 17-silyl enol ether and a palladium catalyzed coupling of an 11 beta-(4-aryltriflate) with tributyl(1-ethoxyethenyl)stannane or diethyl(3-pyridinyl)borane. The new progestelone antagonists were tested for their biological activities and compared to those of known antiprogestins.

  DOI：

  10.1016/0039-128x(94)90024-8

文献信息

• 14.beta.-H-, 14-and 15-En-11.beta.-aryl-4-oestrenes
  申请人：Schering Aktiengesellschaft

  公开号：US05426102A1

  公开（公告）日：1995-06-20

  Novel compounds of the general formula I ##STR1## and the pharmacologically tolerable addition salts thereof with acids are described, in which either Ia) R.sup.11 represents a hydrogen atom in the .beta.-configuration and each of R.sup.12 and R.sup.13 represents a hydrogen atom, or Ib) R.sup.11 represents a hydrogen atom in the .beta.-configuration and R.sup.12 and R.sup.13 together represent a second bond, or Ic) R.sup.11 and R.sup.12 together represent a second bond and R.sup.13 represents a hydrogen atom, or Id) R.sup.11 represents a hydrogen atom in the .alpha.-configuration and R.sup.12 and R.sup.13 together represent a second bond, and in Ia), Ib), Ic) or Id) X represents an oxygen atom, the hydroxyimino grouping >N.about.OH or two hydrogen atoms, R.sup.1 represents a hydrogen atom or a methyl group, R.sup.2 represents a hydroxy group, a C.sub.1 -C.sub.10 -alkoxy group or a C.sub.1 -C.sub.10 -acyloxy group, and R.sup.3 and R.sup.4 have the meanings customary for competitive progesterone antagonists specified in the description. The invention relates also to processes for the preparation of the novel compounds, to pharmaceutical compositions containing those compounds, to their use for the manufacture of medicaments, and to the novel intermediates required for the process. The novel compounds have a strong affinity for the gestagen receptor and exhibit pronounced antigestagenic and also antiglucocorticoid, antimineralocorticoid and antiandrogenic properties.

  描述了通式I ##STR1## 及其与酸的药理学可耐受的加合物盐，其中Ia）R.sup.11代表β-构型中的氢原子，R.sup.12和R.sup.13中的每一个代表氢原子，或Ib）R.sup.11代表β-构型中的氢原子，R.sup.12和R.sup.13共同代表第二键，或Ic）R.sup.11和R.sup.12共同代表第二键，R.sup.13代表氢原子，或Id）R.sup.11代表α-构型中的氢原子，R.sup.12和R.sup.13共同代表第二键，且在Ia）、Ib）、Ic）或Id）中X代表氧原子，羟基亚胺基团>N.about.OH或两个氢原子，R.sup.1代表氢原子或甲基基团，R.sup.2代表羟基、C.sub.1 -C.sub.10 -烷氧基或C.sub.1 -C.sub.10 -酰氧基，R.sup.3和R.sup.4具有描述中规定的竞争孕酮拮抗剂的习惯含义。本发明还涉及制备新化合物的方法、含有这些化合物的药物组合物、用于制造药品的用途，以及所需的新中间体的新化合物。这些新化合物对孕激素受体具有很强的亲和力，表现出明显的抗孕激素和抗糖皮质激素、抗矿皮质激素和抗雄激素特性。
• Synthesis and biological activity of 17-chloro-16(17) unsaturated D-homo antiprogestins
  作者：Wolfgang Schwede、Arwed Cleve、Günter Neff、Eckhard Ottow、Klaus Stöckemann、Rudolf Wiechert

  DOI：10.1016/0039-128x(94)90024-8

  日期：1994.3

  An efficient approach to 17-chloro-16(17) unsaturated D-homo antiprogestins is described. The key steps of the synthesis are a ring-expansion via dichlorocarbene addition to a 17-silyl enol ether and a palladium catalyzed coupling of an 11 beta-(4-aryltriflate) with tributyl(1-ethoxyethenyl)stannane or diethyl(3-pyridinyl)borane. The new progestelone antagonists were tested for their biological activities and compared to those of known antiprogestins.