17β-Acetoxy-3-methoxy-oestrapentaen-(1,3,5,(10),8,14) | 6825-34-9

• 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: 17β-Acetoxy-3-methoxy-oestrapentaen-(1,3,5,(10),8,14)
• 英文别名: [(13S,17S)-3-methoxy-13-methyl-6,7,11,12,16,17-hexahydrocyclopenta[a]phenanthren-17-yl] acetate
• CAS: 6825-34-9
• 化学式: C₂₁H₂₄O₃
• 分子量: 324.42
• InChiKey: SQVFNNNOBSYIMJ-SFTDATJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  17β-Acetoxy-3-methoxy-oestrapentaen-(1,3,5,(10),8,14) 在 氢气 、 镍 作用下， 以 苯 为溶剂， 45.0~90.0 ℃ 、17.65 MPa 条件下， 以85%的产率得到(+/-)-3-methoxy-8α-estra-1,3,5(10)-trien-17β-ol acetate
  参考文献：
  名称：

  Catalytic hydrogenation on Raney nickel of estra-1,3,5(10),8,14-pentaenes with sterically accessible double bonds

  摘要：

  The catalytic hydrogenation of estra-1,3,5(10),8,14-pentaenes with sterically accessible double bonds in the presence of Raney nickel in 2-propanol at elevated pressure and at heating to 110-120 degrees C resulted in prevailing formation of estrogens 8 alpha-analogs alongside a considerable quantity of estra-5,7,9-trienes. Although the hydrogenation at 45-60 degrees C provided a higher yield of estrogens 8 alpha-analogs, the synthesis of steroids of this group gave better results at hydrogenation in a high purity benzene.

  DOI：

  10.1134/s1070428008050060

文献信息

• Process for the selective reduction of a 14, 17-dioxo-8,4-seco-steroid
  申请人：AKZO N.V.

  公开号：EP0069424A1

  公开（公告）日：1983-01-12

  There is provided a process for the selective reduction of 8,14-seco-1,3,5(10),9(11)-oestratetraene-14,17-diones resulting in the corresponding 14,17-ketols with a higher enantioselectivity than obtainable hitherto and a high diastereoselectivity (trans/cis- or cis/trans-ratio) by using a chiral reducing agent consisting of a complex alkali metal aluminiumhydride having the formula M Al(OR1)m(OR2)nH4-m-n, in which M represents an alkali metal; OR is derived from the chiral alcohol (+)-(2S,3R)-4-dimethylamino-3-methyl-1,2-diphenyl-2-butanol or the enantiomer thereof with the (-)-(2R,3S)-configuration; OR2 is derived from an achiral organic hydroxy compound having 1-10 C-atoms; m = 1-3; n = 0-2; and m + n ≤ 3.

  提供了一种选择性还原 8,14-seco-1,3,5(10),9(11)-雌甾-14,17-四烯-14,17-二酮的工艺，该工艺通过使用一种手性还原剂得到相应的 14,17-酮，该还原剂的对映体选择性比迄今为止所能得到的要高，并且具有很高的非对映选择性（反式/顺式或顺式/反式比），该手性还原剂由具有以下式子的复合碱金属铝酸酐组成 M Al(OR1)m(OR2)nH4-m-n，其中 M 代表碱金属； OR 源自手性醇 (+)-(2S,3R)-4-dimethylamino-3-methyl-1,2-diphenyl-2-butanol 或其具有 (-)-(2R,3S)-configuration 的对映体； OR2 来自具有 1-10 个 C 原子的非手性有机羟基化合物； m = 1-3；n = 0-2；且 m + n ≤ 3。
• Dispironaphthalenones and spironaphthalenones as novel dehydrogenation reagents
  作者：Tirumalai R. Kasturi、Jitendra A. Sattigeri

  DOI：10.1016/s0040-4020(01)88233-8

  日期：1992.1

  Dehydrogenation of a number of dihydroaromatic substrates has been carried out using either dispironaphthalenone 1 or spironaphthalenones 2 & 3 as dehydrogenating agents. The reaction is over in refluxing mesitylene in 1-2 hr and the yields of the aromatised products are fairly good (65-70%).
• Catalytic hydrogenation on Raney nickel of estra-1,3,5(10),8,14-pentaenes with sterically accessible double bonds
  作者：S. N. Morozkina、S. V. Nikolaev、S. I. Selivanov、D. B. Ushakov、A. G. Shavva

  DOI：10.1134/s1070428008050060

  日期：2008.5

  The catalytic hydrogenation of estra-1,3,5(10),8,14-pentaenes with sterically accessible double bonds in the presence of Raney nickel in 2-propanol at elevated pressure and at heating to 110-120 degrees C resulted in prevailing formation of estrogens 8 alpha-analogs alongside a considerable quantity of estra-5,7,9-trienes. Although the hydrogenation at 45-60 degrees C provided a higher yield of estrogens 8 alpha-analogs, the synthesis of steroids of this group gave better results at hydrogenation in a high purity benzene.