3-(t-butyldimethylsilyloxy)estra-1,3,5(10),15-tetraen-17-one | 181866-29-5

• 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: 3-(t-butyldimethylsilyloxy)estra-1,3,5(10),15-tetraen-17-one
• 英文别名: 3-tert-butyldimethylsilyloxy-estra-1,3,5(10),15-tetraen-17-one；3-tert-butyldimethylsiloxy-estra-1,3,5(10),15-tetraen-17-one；(8R,9S,13S,14S)-3-[tert-butyl(dimethyl)silyl]oxy-13-methyl-7,8,9,11,12,14-hexahydro-6H-cyclopenta[a]phenanthren-17-one
• CAS: 181866-29-5
• 化学式: C₂₄H₃₄O₂Si
• 分子量: 382.618
• InChiKey: SVEZEYWTMLXNPJ-YOEKFXIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.27
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(t-butyldimethylsilyloxy)estra-1,3,5(10),15-tetraen-17-one 在 palladium on activated charcoal 甲醇 、 正丁基锂 、 氢气 、 对甲苯磺酸 、 二异丙胺 作用下， 以 甲醇 为溶剂， -78.0~25.0 ℃ 、101.33 kPa 条件下， 反应 62.0h， 生成 Trifluoro-methanesulfonic acid (8R,9S,13S,14S)-3-(tert-butyl-dimethyl-silanyloxy)-14-hydroxy-13-methyl-7,8,9,11,12,13,14,15-octahydro-6H-cyclopenta[a]phenanthren-17-yl ester
  参考文献：
  名称：

  5-(Trimethylstannyl)-2H-pyran-2-one and 3-(Trimethylstannyl)-2H-pyran-2-one:  New 2H-Pyran-2-one Synthons

  摘要：

  5-(Trimethylstannyl)-2H-pyran-2-one (11) and 3-(trimethylstannyl)-2H-pyran-2-one (30), readily prepared from the corresponding bromo-2H-pyran-2-ones, undergo Pd(0)-catalyzed coupling reactions with a variety of enol triflates to give 5- and 3- substituted 2H-pyran-2-ones, respectively, This reaction is applicable to the enol triflates of 14 beta-hydroxy-17-ketosteroids, and therefore may prove useful in convergent syntheses of lucibufagins and bufadienolides.

  DOI：

  10.1021/jo951394t
• 作为产物：
  描述：

  3-(O-tert-butyl(dimethyl)silyl)estrone 在 咪唑 、 copper(ll) bromide 作用下， 以 甲醇 为溶剂， 反应 8.0h， 生成 3-(t-butyldimethylsilyloxy)estra-1,3,5(10),15-tetraen-17-one
  参考文献：
  名称：

  [EN] PROCESS FOR THE PRODUCTION OF ESTETROL INTERMEDIATES
  [FR] PROCÉDÉ POUR LA PRODUCTION D'INTERMÉDIAIRES D'ESTÉTROL

  摘要：

  本发明涉及一种制备式(I)化合物的方法，包括以下步骤：a) 将式(II)化合物与硅化或酰化试剂反应，生成式(III)化合物，其中P1是从R2-Si-R3R4或R1CO-中选择的保护基，R1是从C1-6烷基或C3-6环烷基中选择的基团，每个基团可选地被一个或多个独立选择的氟或C1-4烷基取代；R2、R3和R4分别是从C1-6烷基或苯基中选择的基团，每个基团可选地被一个或多个独立选择的氟或C1-4烷基取代；b) 卤代或亚砜化式(III)化合物，生成式(IV)化合物；其中X是卤素，或-O-SO-R5，R5是从C6-10芳基或杂环芳基中选择的基团，每个基团可选地被一个或多个独立选择的氯或C1-4烷基取代；c) 去卤或去亚砜化式(IV)化合物，生成式(V)化合物；d) 将式(V)化合物与还原剂反应，生成式(I)化合物。

  公开号：

  WO2012164095A1

文献信息

• [EN] PROCESS FOR THE PRODUCTION OF ESTETROL INTERMEDIATES<br/>[FR] PROCÉDÉ POUR LA PRODUCTION D'INTERMÉDIAIRES D'ESTÉTROL
  申请人：ESTETRA S A

  公开号：WO2012164096A1

  公开（公告）日：2012-12-06

  The present invention relates to a process for the preparation of a compound of formula (I) said process comprising the steps of : a) reacting a compound of formula (II), with an acylating or a silylating agent to produce a compound of formula (III), wherein P1 and P2 are each independently a protecting group selected from R2-Si-R3R4, or R1CO-, wherein R1 is a group selected from C1-6alkyl or C3-6cycloalkyl, each group being optionally substituted by one or more substituents independently selected from fluoro or C1-4alkyl; R2, R3 and R4 are each independently a group selected from C1-6alkyl or phenyl, each group being optionally substituted by one or more substituents independently selected from fluoro or C1-4alkyl; b) reacting the compound of formula (III) in the presence of palladium acetate or a derivative thereof to produce compound of formula (IV); and c) reacting the compound of formula (IV) with a reducing agent to produce compound of formula (I).

  本发明涉及一种制备化合物的方法，其化学式为(I)，所述方法包括以下步骤：a)将化合物的化学式为(II)与酰化剂或硅化剂反应，生成化合物的化学式为(III)，其中P1和P2分别独立地为选自R2-Si-R3R4或R1CO-的保护基，其中R1是选自C1-6烷基或C3-6环烷基的基团，每个基团可选择性地被一个或多个氟或C1-4烷基取代；R2、R3和R4分别独立地为选自C1-6烷基或苯基的基团，每个基团可选择性地被一个或多个氟或C1-4烷基取代；b)在钯醋酸或其衍生物存在下，将化合物的化学式为(III)反应，生成化合物的化学式为(IV)；c)将化合物的化学式为(IV)与还原剂反应，生成化合物的化学式为(I)。
• [EN] 15β-SUBSTITUTED ESTRONE DERIVATIVES AS SELECTIVE INHIBITORS OF 17β-HYDROXYSTEOID-DEHYDROGENASES, METHOD OF PREPARATION AND USE THEREOF<br/>[FR] DÉRIVÉS D'ŒSTRONE SUBSTITUÉS EN 15Β EN TANT QU'INHIBITEURS SÉLECTIFS DE 17Β-HYDROXYSTÉROÏDES DÉSHYDROGÉNASES, LEUR PROCÉDÉ DE PRÉPARATION ET LEUR UTILISATION
  申请人：USTAV ORGANICKE CHEMIE A BIOCHEMIE AV CR V V I

  公开号：WO2017211330A1

  公开（公告）日：2017-12-14

  15β-substituted derivatives of estrone of general formula I wherein R1, R2, R3, R4, R5 are independently selected from the group consisting of: C1-C4 alkyl, C1-C4 alkoxy, C1-C4 halogenalkyl, halogen, COOR6 wherein R6 is C1-C4 alkyl; H, OH; optionally, R3, R4 and R5 are each formed by a hydrogen atom, while R1 and R2 together form an aryl group, preferably naphthyl; wherein the aromatic ring in position C-15 can be mono-, di-, tri-, tetra- and penta- substituted with substituents R1-R5. Compounds of the invention may be used for diagnosis and possibly also for the treatment of estrogen-dependent diseases.

  通式I的15β-取代雌酮衍生物，其中R1、R2、R3、R4、R5分别独立地选择自以下组：C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基、卤素、COOR6，其中R6是C1-C4烷基；H、OH；可选地，R3、R4和R5各自由氢原子形成，而R1和R2共同形成芳基，优选萘基；其中位置C-15的芳环可以是单取代、双取代、三取代、四取代和五取代，取代基为R1-R5。该发明的化合物可用于诊断和可能治疗雌激素依赖性疾病。
• [EN] PROCESSES FOR THE PREPARATION OF ESTETROL AND INTERMEDIATES THEREOF<br/>[FR] PROCÉDÉS POUR PRÉPARER DE L'ESTÉTROL ET SES INTERMÉDIAIRES
  申请人：[en]NEWCHEM S.P.A.

  公开号：WO2023001866A1

  公开（公告）日：2023-01-26

  A process for the preparation of a compound of formula (IIa) is described where A is a silyl protecting group, in high diastereoisomeric purity and in crystalline form, comprising the crystallization of a mixture of the compound of formula (IIa) and its isomer of formula (IIb), where A is a silyl protecting group, from an ethereal solvent. The invention also provides a process for preparing Estetrol of formula (I) in high diastereoisomeric purity, comprising the use of the compound of formula (IIa), in a crystalline form, as a starting material.
• [EN] PROCESS FOR THE PRODUCTION OF ESTETROL INTERMEDIATES<br/>[FR] PROCÉDÉ DE PRODUCTION D'INTERMÉDIAIRES D'ESTÉTROL
  申请人：[en]MITHRA R&D SA

  公开号：WO2023209017A1

  公开（公告）日：2023-11-02

  The present invention relates to a process for the preparation of a compound of formula (I), a stereoisomer, a salt, a hydrate or a solvate thereof, comprising the step of desulfinylation of a compound of formula (II) to produce compound of formula (I); wherein: R1and R2are as defined in the claims, wherein said desulfinylation step is performed by continuous flow process.
• WO2023/21026
  申请人：——

  公开号：——

  公开（公告）日：——