(8R,9S,10R,13S,14S,17S)-10,13-二甲基-3-亚甲基-1,2,6,7,8,9,11,12,14,15,16,17-十二氢环戊烯并[a]菲-17-醇 | 21952-93-2

• 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
• 中文名称: (8R,9S,10R,13S,14S,17S)-10,13-二甲基-3-亚甲基-1,2,6,7,8,9,11,12,14,15,16,17-十二氢环戊烯并[a]菲-17-醇
• 英文名称: 17β-hydroxy-3-methyleneandrost-4-ene
• 英文别名: 3-methyleneandrost-4-en-17β-ol；3-methylen-androst-4-en-17β-ol；3-methylidene-17β-hydroxy-androst-4-ene；(8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3-methylene-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-ol；(8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3-methylidene-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-ol
• CAS: 21952-93-2
• 化学式: C₂₀H₃₀O
• 分子量: 286.458
• InChiKey: XBIDKWMHMCYHQY-RABCQHRBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (8R,9S,10R,13S,14S,17S)-10,13-二甲基-3-亚甲基-1,2,6,7,8,9,11,12,14,15,16,17-十二氢环戊烯并[a]菲-17-醇 在 sodium hydroxide 、 硼烷 、 双氧水 作用下， 生成 4α,17β-dihydroxy-3β-hydroxymethyl-5α-androstane
  参考文献：
  名称：

  Boynton, Juliette A.; Hanson, James R.; Liman, Mansur D., Journal of Chemical Research, Miniprint, 1998, # 7, p. 1616 - 1631

  摘要：

  DOI：
• 作为产物：
  描述：

  睾酮 、 甲基三苯基溴化膦 在 potassium tert-butylate 作用下， 以 四氢呋喃 、 二甲基亚砜 、 mineral oil 为溶剂， 以797 mg的产率得到(8R,9S,10R,13S,14S,17S)-10,13-二甲基-3-亚甲基-1,2,6,7,8,9,11,12,14,15,16,17-十二氢环戊烯并[a]菲-17-醇
  参考文献：
  名称：

  非质子反应条件下的二硫代烯丙基阳离子 (3 + 2) 环加成：快速获得螺稠合环戊烷支架

  摘要：

  我们报告了一种实现全碳 (3 + 2) 环加成的通用方法，该方法可以从一系列烯烃中合成环戊烯。所需的二硫代烯丙基阳离子试剂可以在新开发的温和方案中从 2-烯丙氧基吡啶前体开始生成，从而避免使用强布朗斯台德酸。这种新方法显着扩大了底物范围，现在还包括酸敏感烯烃，从而能够从简单且容易获得的起始材料制备以前无法获得的螺稠合支架类型。

  DOI：

  10.1039/d3ob01273e

文献信息

• [EN] ESTROGEN RECEPTOR MODULATORS<br/>[FR] MODULATEURS DES RÉCEPTEURS DES ESTROGÈNES
  申请人：MERCK & CO INC

  公开号：WO2006012333A1

  公开（公告）日：2006-02-02

  The present invention relates to compounds and derivatives thereof, their synthesis, and their use as estrogen receptor modulators. The compounds of the instant invention are ligands for estrogen receptors and as such may be useful for treatment or prevention of a variety of conditions related to estrogen functioning including: bone loss, bone fractures, osteoporosis, metastatic bone disease, Paget’s disease, periodontal disease, cartilage degeneration, endometriosis, uterine fibroid disease, hot flashes, increased levels of LDL cholesterol, cardiovascular disease, impairment of cognitive functioning, cerebral degenerative disorders, restenosis, gynecomastia, vascular smooth muscle cell proliferation, obesity, incontinence, inflammation, inflammatory bowel disease, sexual dysfunction, hypertension, retinal degeneration and cancer, in particular of the breast, uterus and prostate.

  本发明涉及化合物及其衍生物，它们的合成以及它们作为雌激素受体调节剂的用途。本发明的化合物是雌激素受体的配体，因此可能对治疗或预防与雌激素功能相关的各种疾病具有用处，包括：骨质流失、骨折、骨质疏松症、转移性骨病、帕盖特病、牙周病、软骨退化、子宫内膜异位症、子宫肌瘤病、潮热、低密度脂蛋白胆固醇水平升高、心血管疾病、认知功能障碍、脑退行性疾病、再狭窄、男性乳腺发育、血管平滑肌细胞增殖、肥胖、失禁、炎症、炎症性肠病、性功能障碍、高血压、视网膜退行性疾病和癌症，特别是乳腺、子宫和前列腺癌。
• Estrogen Receptor Modulators
  申请人：Blizzard A. Timothy

  公开号：US20070203102A1

  公开（公告）日：2007-08-30

  The present invention relates to compounds and derivatives thereof, their synthesis, and their use as estrogen receptor modulators. The compounds of the instant invention are ligands for estrogen receptors and as such may be useful for treatment or prevention of a variety of conditions related to estrogen functioning including: bone loss, bone fractures, osteoporosis, metastatic bone disease, Paget's disease, periodontal disease, cartilage degeneration, endometriosis, uterine fibroid disease, hot flashes, increased levels of LDL cholesterol, cardiovascular disease, impairment of cognitive functioning, cerebral degenerative disorders, restenosis, gynecomastia, vascular smooth muscle cell proliferation, obesity, incontinence, inflammation, inflammatory bowel disease, sexual dysfunction, hypertension, retinal degeneration and cancer, in particular of the breast, uterus and prostate.

  本发明涉及化合物及其衍生物、它们的合成以及它们作为雌激素受体调节剂的用途。本发明的化合物是雌激素受体的配体，因此可能用于治疗或预防与雌激素功能相关的各种疾病，包括：骨质流失、骨折、骨质疏松症、转移性骨病、帕吉特病、牙周病、软骨退化、子宫内膜异位症、子宫肌瘤病、潮热、低密度脂蛋白胆固醇水平升高、心血管疾病、认知功能障碍、脑退行性疾病、再狭窄、男性乳房发育、血管平滑肌细胞增殖、肥胖、失禁、炎症、炎性肠病、性功能障碍、高血压、视网膜退化和癌症，特别是乳腺癌、子宫癌和前列腺癌。
• Androstene-3,5-dienes as ER-β selective SERMs
  作者：Timothy A. Blizzard、Candido Gude、Jerry D. Morgan、Wanda Chan、Elizabeth T. Birzin、Marina Mojena、Consuelo Tudela、Fang Chen、Kristin Knecht、Qin Su、Bryan Kraker、Ralph T. Mosley、Mark A. Holmes、Susan P. Rohrer、Milton L. Hammond

  DOI：10.1016/j.bmcl.2007.09.001

  日期：2007.11

  A series of androstene-3,5-diene derivatives were prepared. Despite lacking the C-3 hydroxyl previously believed necessary for ER activity, some of the analogs retained surprising affinity for ER-beta. For example, diene 4 retained excellent selectivity and potency as an ER-beta agonist and was more selective for ER-beta over the androgen receptor (AR). (C) 2007 Elsevier Ltd. All rights reserved.
• Synthesis of Steroidal Methylene Compounds by the Wittig Reaction¹
  作者：Franz Sondheimer、Raphael Mechoulam

  DOI：10.1021/ja01575a054

  日期：1957.9
• ESTROGEN RECEPTOR MODULATORS
  申请人：Merck & Co., Inc.

  公开号：EP1773862A1

  公开（公告）日：2007-04-18