6-oxa-8α-estrone methyl ether | 1151687-43-2

• 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: 6-oxa-8α-estrone methyl ether
• 英文别名: 3-methoxy-6-oxa-8α-estra-1,3,5(10)-trien-17-one；(3aS,3bS,9bS,11aS)-7-methoxy-11a-methyl-2,3,3a,3b,4,9b,10,11-octahydroindeno[4,5-c]chromen-1-one
• CAS: 1151687-43-2
• 化学式: C₁₈H₂₂O₃
• 分子量: 286.371
• InChiKey: OBCOZGXLCBVXSS-FHIHXZLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 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：

  6-oxa-8α-estrone methyl ether 在 sodium tetrahydroborate 、 三氟化硼乙醚 、 sodium hydride 作用下， 以 四氢呋喃 、 二甲基亚砜 、 mineral oil 为溶剂， 反应 0.67h， 生成
  参考文献：
  名称：

  New analogs of steroid estrogens

  摘要：

  Aiming at the investigation of the mechanism of functioning of steroid estrogens a series of compounds with unnatural rings junction was synthesized. All investigated compounds exhibit a reduced uterotropic activity. It was established applying the NMR spectroscopy that 7 alpha-methyl-3-methoxy-D-homo-6-oxa-8 alpha,14 beta-estra-1,3,5(10)-trien-17a-one existed in solution in two conformations distinguished by the structure of the rings B, C, and D simultaneously. The reaction of 17-methylidene-3-methoxy-6-oxa-8 alpha-estra-1,3,5(10)-triene with hydrobromic acid in acetic acid promotes a rearrangement with the migration of a methyl group into the position 17 resulting in the formation of 17,17-dimethyl-6-oxa-8 alpha-gona-1,3,5(10),13(14)-tetraene derivatives.

  DOI：

  10.1134/s1070428011080203
• 作为产物：
  描述：

  (S)-7-methoxy-11a-methyl-4,10,11,11a-tetrahydroindeno[4,5-c]chromen-1(2H)-one 在 palladium 10% on activated carbon 氢气 作用下， 以 四氢呋喃 为溶剂， 以64%的产率得到6-oxa-8α-estrone methyl ether
  参考文献：
  名称：

  [EN] PREPARATION OF 6-OXA-8ALPHA-STEROID ESTROGEN ANALOGUES - A NEW GROUP OF UNNATURAL ESTROGENS AND THEIR USE IN MEDICINE
  [FR] PRÉPARATION D'ANALOGUES DE L'OETROGÈNE 6-OXA-8?-STÉROÏDE - UN NOUVEAU GROUPE D'OETROGÈNES NON NATURELS ET LEUR UTILISATION EN MÉDECINE

  摘要：

  公开号：

  WO2009059806A3

文献信息

• Selivanov; Tsogoeva; Shavva, Russian Journal of Organic Chemistry, <hi>1998</hi>, vol. 34, # 9, p. 1292 - 1296
  作者：Selivanov、Tsogoeva、Shavva

  DOI：——

  日期：——
• PREPARATION OF 6-OXA-8ALPHA-STEROID ESTROGEN ANALOGUES - A NEW GROUP OF UNNATURAL ESTROGENS AND THEIR USE IN MEDICINE
  申请人：Pison Ulrich

  公开号：US20110160296A1

  公开（公告）日：2011-06-30

  The invention is related to the area of new 6-Oxa-8α-steroid estrogen analogues and the synthesis of these new biological active steroid estrogen analogues, namely, to the preparation of 6-oxa-8α-steroid estrogens and their use as estrogen receptor modulators. These new estrogen analogues are ligands for estrogen receptors and as such may be useful for the treatment and prevention of a variety of conditions related to estrogen functioning. These conditions include bone and cartilage disorders, increased levels of LDL cholesterol, cardiovascular diseases, impairment of cognitive function, cerebral degeneration disorders, endometriosis and other types of inflammation, the metabolic syndrome, and cancer, in particular of the breast, uterus and prostate.