(17α)-3-methoxyestra-1,3,5(10),15-tetraen-17-ol | 59126-64-6

• 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)-3-methoxyestra-1,3,5(10),15-tetraen-17-ol
• 英文别名: 3-methoxy-1,3,5(10),15-estratetraen-17α-ol；3-methoxy-17α-hydroxyestra-1,3,5(10),15-tetraene；3-Methoxy-1,3,5(10),15-estratetraen-17alpha-ol；(8R,9S,13S,14S,17R)-3-methoxy-13-methyl-6,7,8,9,11,12,14,17-octahydrocyclopenta[a]phenanthren-17-ol
• CAS: 59126-64-6
• 化学式: C₁₉H₂₄O₂
• 分子量: 284.398
• InChiKey: KAECVEVIXKMEOP-FQBWVUSXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (17α)-3-methoxyestra-1,3,5(10),15-tetraen-17-ol 在 锌铜偶 、 三丁基膦 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 乙醚 为溶剂， 反应 34.0h， 生成 (15β,16β)-15,16-dihydro-3-methoxy-17-(phenylseleno)-3'H-cycloprop<15,16>estra-1,3,5(10),15-tetraene
  参考文献：
  名称：

  自由基开环的合成应用：环丙基甲基自由基的使用

  摘要：

  环状烯丙基醇的环丙烷化，然后进行自由基脱氧，通过环丙基甲基系统的周边开环，导致烷基取代的环烯烃（方案1）；烷基本身可以被取代（在环丙烷化阶段），可以使用烯丙基醇的合成等价物，整个过程以可预测的立体化学和区域化学发生。

  DOI：

  10.1039/c39890000332
• 作为产物：
  描述：

  3-methoxy-estra-1,3,5(10),15-tetraen-17-one 生成 (17α)-3-methoxyestra-1,3,5(10),15-tetraen-17-ol
  参考文献：
  名称：

  自由基开环的合成应用：环丙基甲基自由基的使用

  摘要：

  环状烯丙基醇的环丙烷化，然后进行自由基脱氧，通过环丙基甲基系统的周边开环，导致烷基取代的环烯烃（方案1）；烷基本身可以被取代（在环丙烷化阶段），可以使用烯丙基醇的合成等价物，整个过程以可预测的立体化学和区域化学发生。

  DOI：

  10.1039/c39890000332

文献信息

• 19-NOR-STEROID DERIVATIVES WITH A 15ALPHA, 16ALPHA-METHYLENE GROUP AND A SATURATED 17, 17-SPIRO-LACTONE RING, USE THEREOF, AND MEDICAMENTS CONTAINING SAID DERIVATIVES
  申请人：Klar Ulrich

  公开号：US20100311702A1

  公开（公告）日：2010-12-09

  The 15α,16α-methylene-17-hydroxy-19-nor-17-pregna-4-en-3-one-21-carboxylic acid γ-lactone derivatives of the present invention possess progestational efficacy. They have the general chemical formula I, in which Z is selected from the group comprising an oxygen atom, two hydrogen atoms, NOR and NNHSO 2 R, where R is hydrogen, C 1 -C 10 -alkyl, aryl or C 7 -C 20 -aralkyl, R 4 is hydrogen or halogen, and moreover either: R 6a , R 6b together form methylene or 1,2-ethanediyl or R 6a is hydrogen and R 6b is selected from the group comprising hydrogen, C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl or C 2 -C 10 -alkynyl, and R 7 is selected from the group comprising hydrogen, C 1 -C 10 -alkyl, C 3 -C 6 -cycloalkyl, C 2 -C 10 -alkenyl or C 2 -C 10 -alkynyl, or: R 6a is hydrogen and R 6b and R 7 , together, denote a bond, an oxygen or form methylene, R 18 represents hydrogen or C 1 -C 3 -alkyl and in addition include their solvates, hydrates, stereoisomers and salts.

  本发明的15α,16α-亚甲基-17-羟基-19-去-17-孕烷-4-烯-3-酮-21-羧酸γ-内酯衍生物具有孕酮效应。它们具有通用化学式I，其中Z选自包括氧原子、两个氢原子、NOR和NNHSO2R的群，其中R为氢、C1-C10-烷基、芳基或C7-C20-芳基烷基，R4为氢或卤素，而且还有以下情况之一：R6a，R6b共同形成亚甲基或1,2-乙二基或R6a为氢且R6b选自包括氢、C1-C10-烷基、C2-C10-烯基或C2-C10-炔基的群，R7选自包括氢、C1-C10-烷基、C3-C6-环烷基、C2-C10-烯基或C2-C10-炔基的群，或：R6a为氢且R6b和R7共同表示键合、氧或亚甲基，R18代表氢或C1-C3-烷基，另外还包括它们的溶剂化合物、水合物、立体异构体和盐。
• 15,16-Methylene-17-hydroxy-19-nor-21-carboxylic acid-steroid Y-lactone derivative, use thereof and medicinal products containing the derivative
  申请人：Klar Ulrich

  公开号：US20110015162A1

  公开（公告）日：2011-01-20

  The invention relates to 15,16-methylene-17-hydroxy-19-nor-21-carboxylic acid-steroid γ-lactone derivatives with the general chemical formula I, and R 4 , R 6a , R 6b , R 7 and Z have the meanings stated in claim 1 , and their solvates, hydrates, stereoisomers and salts. The invention further relates to the use of these derivatives for the production of a medicinal product for oral contraception and for the treatment of pre-, peri- and postmenopausal complaints and medicinal products that contain said derivatives. The derivatives according to the invention have a progestational and in preferred cases additionally an antimineralocorticoid and neutral to slightly androgenic action.

  该发明涉及具有通用化学式I的15,16-亚甲基-17-羟基-19-去-21-羧酸类固醇γ-内酯衍生物，其中R4、R6a、R6b、R7和Z的含义如权利要求1所述，并且它们的溶剂化合物、水合物、立体异构体和盐。该发明还涉及利用这些衍生物生产用于口服避孕和治疗围绝经前、围绝经期和绝经后症状的药物产品，以及含有该衍生物的药物产品。根据该发明的衍生物具有孕激素作用，在优选情况下还具有抗矿物皮质激素和中性至轻微雄激素作用。
• 15, 16-METHYLENE-17-(1'-PROPENYL)-17,3'-OXIDOESTRA-4-EN-3-ONE DERIVATIVE , USE THEREOF, AND MEDICAMENT CONTAINING SAID DERIVATIVE
  申请人：Klar Ulrich

  公开号：US20110003779A1

  公开（公告）日：2011-01-06

  The invention relates to 15,16-methylene-17-(1′-propenyl)-17-3′-oxidoestra-4-en-3-one derivatives with the general chemical formula I, where the Z, R 4 , R 6a , R 6b , R 7 and R 18 have the meanings stated in claim 1 , and solvates, hydrates and salts thereof, including all crystal modifications and all stereoisomers of these compounds. The invention also relates to the use of these derivatives for the production of a drug for oral contraception and for the treatment of pre-, peri- and postmenopausal problems and drugs which contain such derivatives, in particular use in the aforesaid indications. The derivatives according to the invention have a progestational and in preferable cases also an antimineralcorticoid and neutral to slight androgenic activity.

  该发明涉及具有一般化学式I的15,16-亚甲基-17-(1'-丙烯基)-17-3'-氧化雌甾-4-烯-3-酮衍生物，其中Z、R4、R6a、R6b、R7和R18具有权利要求1中所述的含义，以及其溶剂化物、水合物和盐，包括这些化合物的所有晶体结构和所有立体异构体。该发明还涉及利用这些衍生物生产口服避孕药和用于治疗围绝经期问题的药物，以及含有这种衍生物的药物，特别是用于上述适应症中。根据本发明的衍生物具有孕激素作用，在优选情况下还具有抗矿皮质激素和中性至轻微雄激素活性。
• 17.alpha.-HYDROXY-1,3,5(10),15-ESTRATETRAENES AND PROCESS FOR THEIR
  申请人：Schering Aktiengesellschaft

  公开号：US04016269A1

  公开（公告）日：1977-04-05

  Novel estrogenic 17.alpha.-hydroxy-1,3,5(10),15-estratetraenes of the formula ##STR1## wherein R.sub.1 is H, lower alkyl or lower acyl, R.sub.2 is lower alkyl and R.sub.3 is H, lower alkyl, lower acyl or tetrahydropyranyloxy, are produced by (a) reacting a 16.alpha.,17.alpha.-epoxy-estratriene with lithium halide or HCl in glacial acetic acid; converting the resulting halohydrin into a 16-halo-17-tetrahydropyranyl ether; and splitting off hydrogen halide from therefrom; or (b) reacting the 16.alpha.,17.alpha.-epoxy-estratriene with diphenylselenide and alkali metal borohydride; oxidizing the thus-produced 17.alpha.-hydroxy-16.beta.-phenylselenide to the corresponding phenylselenide oxide; and forming the .DELTA..sup.15 double bond by heating with removal of phenyl--Se--OH.

  该专利描述了一种新的雌激素17.alpha.-羟基-1,3,5（10），15-麦角甾四烯的制备方法。其中，R.sub.1为氢、低碳基或低酰基，R.sub.2为低碳基，R.sub.3为氢、低碳基、低酰基或四氢吡喃氧基。制备方法包括：（a）将16.alpha.，17.alpha.-环氧-麦角甾三烯与溴化锂或HCl在冰乙酸中反应，将生成的卤代醇转化为16-卤代-17-四氢吡喃基醚，并从中分离氢卤酸；或（b）将16.alpha.，17.alpha.-环氧-麦角甾三烯与二苯基硒和碱性金属硼氢化物反应，将产生的17.alpha.-羟基-16.beta.-苯基硒化物氧化为相应的苯基硒氧化物，并通过加热去除苯基--Se--OH形成.DELTA..sup.15双键。
• 19-NOR-STEROID DERIVATIVES WITH A 15a,16a-METHYLENE GROUP AND A SATURATED 17,17-SPIROLACTONE RING, USE THEREOF, AND MEDICAMENTS CONTAINING SAID DERIVATIVES
  申请人：BAYER INTELLECTUAL PROPERTY GmbH

  公开号：US20130123219A1

  公开（公告）日：2013-05-16

  The 15α,16α-methylene-17-hydroxy-19-nor-17-pregna-4-en-3-one-21-carboxylic acid γ-lactone derivatives of the present invention possess progestational efficacy. They have the general chemical formula I, in which Z is selected from the group comprising an oxygen atom, two hydrogen atoms, NOR and NNHSO 2 R, where R is hydrogen, C 1 -C 10 -alkyl, aryl or C 7 -C 20 -aralkyl, R 4 is hydrogen or halogen, and moreover either: R 6a , R 6b together form methylene or 1,2-ethanediyl or R 6a is hydrogen and R 6b is selected from the group comprising hydrogen, C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl or C 2 -C 10 -alkynyl, and R 7 is selected from the group comprising hydrogen, C 1 -C 10 -alkyl, C 3 -C 6 -cycloalkyl, C 2 -C 10 -alkenyl or C 2 -C 10 -alkynyl, or: R 6a is hydrogen and R 6b and R 7 , together, denote a bond, an oxygen or form methylene, R 18 represents hydrogen or C 1 -C 3 -alkyl and in addition include their solvates, hydrates, stereoisomers and salts.

  本发明的15α，16α-亚甲基-17-羟基-19-去氢-17-孕烷-4-烯-3-酮-21-羧酸γ-内酯衍生物具有孕激素功效。它们具有一般化学式I，其中Z选自包括氧原子、两个氢原子、NOR和NNHSO2R的群，其中R为氢、C1-C10烷基、芳基或C7-C20-芳基烷基，R4为氢或卤素，而且要么：R6a，R6b一起形成亚甲基或1,2-乙二基或R6a为氢，R6b选自包括氢、C1-C10烷基、C2-C10烯基或C2-C10炔基，R7选自包括氢、C1-C10烷基、C3-C6环烷基、C2-C10烯基或C2-C10炔基，或者：R6a为氢，R6b和R7一起表示键，氧或形成亚甲基，R18表示氢或C1-C3烷基，并且还包括它们的溶剂化合物、水合物、立体异构体和盐。