Oest-4-en-3-on | 4811-77-2

• 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: Oest-4-en-3-on
• 英文别名: Oestr-4-en-3-on；3-Oxo-19nor-androsten-(4)；Δ⁴-Oestren-3-on；19-Nor-androsten-(4)-on-(3)；estr-4-en-3-one；(8R,9S,10R,13S,14S)-13-methyl-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-one
• CAS: 4811-77-2
• 化学式: C₁₈H₂₆O
• 分子量: 258.404
• InChiKey: JFEPJTGMGDGPHJ-PNKHAZJDSA-N

物化性质

• 熔点：
  202-205 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  389.8±9.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  Oest-4-en-3-on 以78%的产率得到
  参考文献：
  名称：

  PIASCO, A.;NASRAOUI, N.

  摘要：

  DOI：
• 作为产物：
  描述：

  3-甲氧基雌甾-1(10),2,4-三烯 在 2-甲基-2-丁醇 、 lithium 作用下， 生成 Oest-4-en-3-on
  参考文献：
  名称：

  Cherkasov,A.N. et al., Journal of Organic Chemistry USSR (English Translation), 1971, vol. 7, p. 955 - 961

  摘要：

  DOI：

文献信息

• [EN] NEW MONO-AND BISMETHYLENE-STEROID DERIVATIVES AND PROCESS FOR THEIR SYNTHESIS<br/>[FR] NOUVEAUX DERIVES DE MONO-ET BISMETHYLENE-STEROIDE ET PROCEDE DE SYNTHESE DE CEUX-CI
  申请人：RICHTER GEDEON VEGYESZET

  公开号：WO2004101594A1

  公开（公告）日：2004-11-25

  The invention relates to new mono- and bismethylene-steroid derivatives of general formula (I) - wherein Z represents two hydrogen atoms or an oxo group; X and Y independently of each other represent either two hydrogen atoms of a CH2= group, with the restriction that at least one of them is CH2= group and if the meaning of Z is oxo group Y represents two hydrogen atoms, R represents a C1-C4 alkyl group, as well as the pharmaceutical compositions containing the above compounds as active ingredients, and the processes for the synthesis of active ingredients and pharmaceutical compositions. The invention also relates to the methods of treatments with these compounds, which means administering to a mammal to be treated with progestogen - including human - effective amount/amounts of the active ingredients of the present invention as such or as medicament. The mono- and bismethylene-steroid derivatives of the general formula (I) have progestogen effect. They can be used as active ingredients of contraceptive medicaments as such or in combination with an estrogen component. Furthermore, they can be used in the treatment of endometriosis and in the substitution therapy of estrogen as gestagen agent beside the estrogen component. The mono- and bismethylene-steroid derivatives of the general formula (I) of the present invention can be synthesized by reacting a compound of the general formula (II), - wherein the meaning of Z, X and Y is as described for the compounds of formula (I) - with an acid anhydride of the general formula (R-CO)2O or with an acid chloride of the general formula R-CO-Cl - wherein R represents a C1-C4 alkyl group - in the presence of a strong acid.

  该发明涉及一般式(I)的新单甲基和双甲基烷基类固醇衍生物，其中Z代表两个氢原子或一个氧代基；X和Y彼此独立地表示两个氢原子或一个CH2=基团，限制条件是它们中至少有一个是CH2=基团，如果Z的含义是氧代基，则Y代表两个氢原子，R代表C1-C4烷基类团，以及包含上述化合物作为活性成分的药物组合物，以及用于合成活性成分和药物组合物的过程。该发明还涉及使用这些化合物进行治疗的方法，即向待治疗的哺乳动物（包括人类）施用本发明的活性成分的有效量/量，作为药物。一般式(I)的单甲基和双甲基烷基类固醇衍生物具有孕激素效应。它们可以作为避孕药物的活性成分单独使用或与雌激素成分结合使用。此外，它们可以用于治疗子宫内膜异位症，并在雌激素的替代疗法中作为孕激素剂，除了雌激素成分。本发明的一般式(I)的单甲基和双甲基烷基类固醇衍生物可以通过将一般式(II)的化合物与一般式(R-CO)2O的酸酐或一般式R-CO-Cl的酸氯反应而合成，其中Z、X和Y的含义如一般式(I)的化合物所述，R代表C1-C4烷基类团，在强酸存在下进行。
• Microbiological hydroxylation of steroids. Part IV. The pattern of dihydroxylation of mono-oxygenated 5α-androstanes with cultures of the fungus Calonectria decora
  作者：A. M. Bell、P. C. Cherry、I. M. Clark、W. A. Denny、Ewart R. H. Jones、G. D. Meakins、P. D. Woodgate

  DOI：10.1039/p19720002081

  日期：——

  concerned with the relation between the pattern of the dihydroxylation by Calonectria decora of mono-oxygenated 5α-androstane derivatives (mainly ketones), and the position of the oxygen function in the substrate. Terminal ring ketones (3, 4, 16, and 17) are converted, in useful yields, into one or two dihydroxy-ketones. (Ring B and C ketones are much less satisfactory as substrates.) The structures of most

  该工作涉及单加氧的5α-雄烷衍生物（主要是酮）的Calonectria decora的二羟基化的图案与底物中的氧官能团的位置之间的关系。将末端环酮（3、4、16和17）以有用的产率转化为一个或两个二羟基酮。（环丁酮和丙环酮作为底物要令人满意的多。）大多数产品的结构是通过光谱研究得出的。必要时通过化学相关性对这种方法进行补充
• 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。
• 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：US20100317632A1

  公开（公告）日：2010-12-16

  The invention relates to 17-(1′-propenyl)-17-3′-oxidoestra-4-en-3-one derivatives with the general chemical formula I, where the residues Z, R 4 , R 6a , R 6b , R 7 , R 15 , R 16a , R 16b and R 18 have the meanings stated in Claim 1, and their solvates, hydrates and salts, including all stereoisomers of these compounds. 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, and in particular application in the aforementioned indications. 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17-(1'-丙烯基)-17-3'-氧化酯基-4-烯-3-酮衍生物，其中残基Z，R4，R6a，R6b，R7，R15，R16a，R16b和R18具有权利要求1中所述的含义，以及它们的溶剂合物，水合物和盐，包括这些化合物的所有立体异构体。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期症状的药物产品，以及含有所述衍生物的药物产品，并特别适用于上述适应症。根据本发明的衍生物具有孕激素作用，并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。
• [EN] 15ß-SUBSTITUTED STEROIDS HAVING SELECTIVE ESTROGENIC ACTIVITY<br/>[FR] STEROIDES SUBSTITUES EN 15? AYANT UNE ACTIVITE OESTROGENIQUE SELECTIVE
  申请人：AKZO NOBEL NV

  公开号：WO2006027347A1

  公开（公告）日：2006-03-16

  The invention provides 15β-substituted steroidal compounds having selective estrogen receptor activity according to Formula (I) wherein, R1 is H, C1-5 alkyl, C1-12 acyl, di-(C1-5 alkyl)aminocarbonyl, (C1-5alkyl)oxycarbonyl or sulfamoyl, R2 is H, C1-3alkyl, C2-3alkenyl or C2-3alkynyl, each of which may be optionally substituted with a halogen, R3 is C1-2alkyl, ethenyl or ethynyl, each of which may be optionally substituted with a halogen, and R4 is H or C1-12 acyl.

  该发明提供了具有选择性雌激素受体活性的15β-取代类固醇化合物，其化学式为（I），其中，R1为H，C1-5烷基，C1-12酰基，二（C1-5烷基）氨基甲酰基，（C1-5烷基）氧甲酰基或磺胺基，R2为H，C1-3烷基，C2-3烯基或C2-3炔基，每个基可能选择性地被卤素取代，R3为C1-2烷基，乙烯基或乙炔基，每个基可能选择性地被卤素取代，R4为H或C1-12酰基。