10,13-dimethyl-7,8,9,11,12,14,15,17-octahydro-6H-cyclopenta[a]phenanthrene-3,16-dione

• 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: 10,13-dimethyl-7,8,9,11,12,14,15,17-octahydro-6H-cyclopenta[a]phenanthrene-3,16-dione
• 英文别名: 1,4-androstadien-3,16-dione；Androsta-1,4-diene-3,16-dione；(8S,9S,10R,13R,14S)-10,13-dimethyl-7,8,9,11,12,14,15,17-octahydro-6H-cyclopenta[a]phenanthrene-3,16-dione
• 化学式: C₁₉H₂₄O₂
• 分子量: 284.398
• InChiKey: XPMIPSZDLCIVST-SPOLIRPYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  10,13-dimethyl-7,8,9,11,12,14,15,17-octahydro-6H-cyclopenta[a]phenanthrene-3,16-dione 在 氢溴酸 作用下， 生成 1-Hydroxy-4-methyl-oestra-1,3,5(10)-trien-16-on
  参考文献：
  名称：

  Bile Acids and Steroids. XXXV. Some A-Ring Aromatic Steroids having Oxygen Functions at C-16 and Their Pharmacological Activities. (1)

  摘要：

  为了实现降低胆固醇和雌激素作用的理想分离，合成了一些 A 环芳香族 16 酮类固醇。所有这些化合物都缺乏雌激素作用，它们的脂质转移活性也很弱。

  DOI：

  10.1248/cpb.18.2018

文献信息

• The reformatsky reaction of 17-keto-steroids with ethyl α-bromopropionate
  作者：Iwasaki Mitsutaka

  DOI：10.1016/0039-128x(67)90025-6

  日期：1967.4

  Abstract The Reformatsky reaction of 17-keto-steroids with ethyl α-bromopropionate was investigated, and a new decarboxylation reaction of 23-nor-cholan-22-oic acids has been discovered, leading to pregn-17(20)-enes. Such a decarboxylation, however, could not be achieved with those acids prepared by the Reformatsky reactions of 3- and 16-keto-steroids and also of 17-keto-steroids and ethyl monobromoacetate

  摘要 研究了 17-酮类固醇与 α-溴丙酸乙酯的 Reformatsky 反应，并发现了一种新的 23-nor-cholan-22-oic 酸的脱羧反应，生成了 pregn-17(20)-enes。然而，使用通过 3- 和 16- 酮-类固醇以及 17- 酮-类固醇和单溴乙酸乙酯的 Reformatsky 反应制备的那些酸不能实现这种脱羧。
• Bile Acids and Steroids. XXXV. Some A-Ring Aromatic Steroids having Oxygen Functions at C-16 and Their Pharmacological Activities. (1)
  作者：KATSUO SASAKI、TOMOKO IMAI、HITOSHI MINATO、KENICHI TAKEDA

  DOI：10.1248/cpb.18.2018

  日期：——

  In order to achieve the desired separation of cholesterol-lowering and estrogenic effect, some A-ring aromatic 16-keto steroids were synthesised. All of these compounds lacked estrogenic effect and their lipid-shifting activities were also weak.

  为了实现降低胆固醇和雌激素作用的理想分离，合成了一些 A 环芳香族 16 酮类固醇。所有这些化合物都缺乏雌激素作用，它们的脂质转移活性也很弱。