2-脱氢-3-甲氧基替勃龙 | 15506-05-5

• 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
• 中文名称: 2-脱氢-3-甲氧基替勃龙
• 英文名称: 3-Methoxy-7α-methyl-17α-aethinyl-17β-hydroxy-Δ^2,5(10)-19-norandrastadien
• 英文别名: (7R,8R,9S,13S,14S,17R)-17-ethynyl-3-methoxy-7,13-dimethyl-4,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-ol
• CAS: 15506-05-5
• 化学式: C₂₂H₃₀O₂
• 分子量: 326.479
• InChiKey: ONIHVXGVUPKWSJ-PWDNGAOSSA-N

物化性质

• 沸点：
  456.5±45.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)
• 溶解度：
  溶于二氯甲烷、乙酸乙酯

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  2-脱氢-3-甲氧基替勃龙 在 草酸 作用下， 以 甲醇 为溶剂， 生成 替勃龙
  参考文献：
  名称：

  合成von7α -Methyl-3-oxo- Δ4,9,11 -19-norandrostatrienen。ÜberSteroide，211岁。Mitteilung †

  摘要：

  通过用过酸，氧化铝和三氟化硼进行后续处理，可将3-oxo- Δ5 （10），9（11） -19-类固醇轻松转化为3-oxo- Δ4,9,11 -19-类固醇描述。

  DOI：

  10.1002/hlca.19670500602
• 作为产物：
  描述：

  (7alpha,17beta)-3-甲氧基-7-甲基-雌甾-1,3,5(10)-三烯-17-醇 在 氨 、 sodium 、 环己酮 、 aluminum isopropoxide 、 乙二胺 、 叔丁醇 作用下， 以 四氢呋喃 、 二甲基亚砜 、 甲苯 为溶剂， 生成 2-脱氢-3-甲氧基替勃龙
  参考文献：
  名称：

  合成von7α -Methyl-3-oxo- Δ4,9,11 -19-norandrostatrienen。ÜberSteroide，211岁。Mitteilung †

  摘要：

  通过用过酸，氧化铝和三氟化硼进行后续处理，可将3-oxo- Δ5 （10），9（11） -19-类固醇轻松转化为3-oxo- Δ4,9,11 -19-类固醇描述。

  DOI：

  10.1002/hlca.19670500602

文献信息

• [EN] PROCESS FOR THE PRODUCTION OF TIBOLONE<br/>[FR] PROCEDE DE PRODUCTION DE TIBOLONE
  申请人：RESOLUTION CHEMICALS LTD

  公开号：WO2004078774A1

  公开（公告）日：2004-09-16

  Disclosed is a process for the synthesis of 17β-hydroxy-7α-methyl- 19-nor-17α-pregn-5(10)-ene-20-yne-3-one (tibolone, 11) and intermediates useful for the synthesis thereof: (11).

  揭示了一种合成17β-羟基-7α-甲基-19-去甲-17α-孕烷-5(10)-烯-20-炔-3-酮（替布龙，11）及其合成有用的中间体的过程：（11）。
• Process and intermediates to prepare17beta-hydroxy-7alpha-methyl-19-nor-17alpha-pregn -5(10)-en-20-yn-3-one
  申请人：Martynow Jacek

  公开号：US20060111332A1

  公开（公告）日：2006-05-25

  The present invention is a process for the preparation of 17β-hydroxy-7α-methyl-19-nor-17α-pregn-5(10)-en-20-yn-3-one (17α-ethynyl-17β-hydroxy-7α-methyl-5(10)-estren-3-one, tibolone) of formula 1, which comprises hydrolysis of 17α-ethynyl-17β-hydroxy-7α-methyl-5(10)-estrene 3,3 -cyclic ketals of formula 2, where groups R 1 , R 2 , R 3 and R 4 are hydrogen atoms or alkyl groups, or R 1 and R 3 , taken together with the carbon atoms within the dioxolane ring to which they are attached, form an alicyclic ring fused to the dioxolane ring, with R 2 and R 4 being hydrogen atoms, or R 1 and R 3 together with the carbon atoms to which they are attached form an aromatic ring fused to the dioxolane ring, where R 2 and R 4 , taken together, form a chemical bond within said aromatic ring. In addition, the present invention includes an intermediate, compound of formula 2 and two processes to prepare 17α-ethynyl-17β-hydroxy-7α-methyl-5(10)-estrene 3,3 -cyclic ketals of formula 2: (a) by contacting 17α-ethynyl-17β-hydroxy-7α-methyl-4-estren-3-one with vicinal diols in the presence of a protic acid, and (b) by contacting 7α-methyl-5(10)-estrene-17-one 3,3-cyclic ketals of formula 4, where R 1 -R 4 are defined as above, with metal acetylides, in inert solvents.

  本发明涉及一种制备17β-羟基-7α-甲基-19-去氢-17α-孕-5（10）-烯-20-炔-3-酮（17α-乙炔基-17β-羟基-7α-甲基-5（10）-雌甾-3-酮，替泼酮）的方法，其包括对式2的17α-乙炔基-17β-羟基-7α-甲基-5（10）-雌甾-3,3-环糊精酮进行水解，其中基团R1、R2、R3和R4是氢原子或烷基，或者R1和R3与它们所附着的二氧兰环内的碳原子一起形成螺环并与二氧兰环融合，其中R2和R4是氢原子，或者R1和R3与它们所附着的碳原子一起形成与二氧兰环融合的芳香环，其中R2和R4一起在该芳香环内形成化学键。此外，本发明还包括一个中间体，化合物的式子为2，并且还包括两种制备式2的17α-乙炔基-17β-羟基-7α-甲基-5（10）-雌甾-3,3-环糊精酮的方法：（a）通过在质子酸存在下与邻二醇接触17α-乙炔基-17β-羟基-7α-甲基-4-雌甾-3-酮，和（b）通过在惰性溶剂中与金属乙炔基化合物接触式4的7α-甲基-5（10）-雌甾-17-酮3,3-环糊精酮，其中R1-R4的定义如上。
• PROCESS AND INTERMEDIATES TO PREPARE 17.BETA.-HYDROXY-7.ALFA.-METHYL-19-NOR-17.ALFA.-PREGN-5(10)-EN-20-YN-3-ONE
  申请人：INSTYTUT FARMACEUTYCZNY

  公开号：EP1556407A2

  公开（公告）日：2005-07-27
• [EN] PROCESS AND INTERMEDIATES TO PREPARE l7ß-hydroxy-7alpha-methyl-19-nor-17alpha-pregn-5(10)-en-20-yn-3-one<br/>[FR] PROCEDE ET INTERMEDIAIRES POUR LA PREPARATION DE L7ss-HYDROXY-7 DOLLAR G(A)-METHYL-19-NOR-1720040415
  申请人：PRZED FARMACEUTYCZNE ANPHARM S

  公开号：WO2004031204A2

  公开（公告）日：2004-04-15

  The present invention is a process for the preparation of l7ß-hydroxy-7α-methyl-19-nor-17α-pregn-5(10)-en-20-yn-3-one (17α-ethynyl-l7ß-hydroxy-7α-methyl-5(10)-estren-3-one, tibolone) of formula 1, which comprises hydrolysis of 17α-ethynyl-l7ß-hydroxy-7α-methyl-5(10)-estrene 3,3-cyclic ketals of formula 2, where groups R1, R2, R3 and R4 are hydrogen atoms or alkyl groups, or R1 and R3, taken together with the carbon atoms within the dioxolane ring to which they are attached, form an alicyclic ring fused to the dioxolane ring, with R2 and R4 being hydrogen atoms, or R1 and R3 together with the carbon atoms to which they are attached form an aromatic ring fused to the dioxolane ring, where R2 and R4, taken together, form a chemical bond within said aromatic ring. In addition, the present invention includes an intermediate, compound of formula 2 and two processes to prepare 17α-ethynyl-17(3-hydroxy-7α-methyl-5(10)-estrene 3,3-cyclic ketals of formula 2: (a) by contacting 17α-ethynyl-l7ßhydroxy-7α-methyl-4-estren-3-one with vicinal diols in the presence of a protic acid, and (b) by contacting 7α-methyl-5(10)-estrene-17-one 3,3-cyclic ketals of formula 4, where R1-R4 are defined as above, with metal acetylides, in inert solvents.
• Synthese von 7?-Methyl-3-oxo-?4,9,11-19-norandrostatrienen. �ber Steroide, 211. Mitteilung
  作者：P. Wieland、G. Anner

  DOI：10.1002/hlca.19670500602

  日期：——

  The easy conversion of 3-oxo-Δ5(10),9(11)-19-norsteroids into 3-oxo-Δ4,9,11-19-norsteroids by subsequent treatment with a peracid, aluminium oxide, and boron trifluoride is described.

  通过用过酸，氧化铝和三氟化硼进行后续处理，可将3-oxo- Δ5 （10），9（11） -19-类固醇轻松转化为3-oxo- Δ4,9,11 -19-类固醇描述。