3β,17β,19-trihydroxyandrost-5-ene | 3404-23-7

• 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: 3β,17β,19-trihydroxyandrost-5-ene
• 英文别名: 5-androstene-3β,17β,19-triol；Androst-5-ene-3beta,17beta,19-triol；(3S,8R,9S,10S,13S,14S,17S)-10-(hydroxymethyl)-13-methyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol
• CAS: 3404-23-7
• 化学式: C₁₉H₃₀O₃
• 分子量: 306.445
• InChiKey: KPTQFNUKAKVGSS-ACJJDMNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3β,17β,19-trihydroxyandrost-5-ene 在 aluminum isopropoxide 作用下， 以 环己酮 、 甲苯 为溶剂， 生成 19-羟基雄甾-4-烯-3,17-二酮
  参考文献：
  名称：

  C-19 Functional Steroids. V.¹ Synthesis of Estrogen Biosynthesis Intermediates²

  摘要：

  DOI：

  10.1021/jo01041a034
• 作为产物：
  描述：

  3beta-乙酰氧基-19-羟基雄甾-5-烯-17-酮 在 lithium aluminium tetrahydride 作用下， 生成 3β,17β,19-trihydroxyandrost-5-ene
  参考文献：
  名称：

  Steroids CCXXX. Conversion of 6β,19-oxides and lactones into 19-nor steroids

  摘要：

  DOI：

  10.1016/s0039-128x(63)80110-5

文献信息

• The preparation and dienone–phenol rearrangement of androsta-2,5-diene-4,17-dione
  作者：James R. Hanson、David Raines、Steve G. Knights

  DOI：10.1039/p19800001311

  日期：——

  The preparation of androsta-2,5-diene-4,17-dione from dehydroisoandrosterone is described. Its dienone–phenol rearrangement, in the presence of hydrobromic acid and glacial acetic acid, affords 1-methyl-4-hydroxyestra-1,3,5(10)-trin-17-one.

  描述了由脱氢异雄甾酮制备雄甾烯-2,5-二烯-4,17-二酮。在氢溴酸和冰醋酸的存在下，其二烯酮-苯酚重排，可得到1-甲基-4-羟基-1,3,5（10）-trin-17-one。
• [EN] ESTROGEN RECEPTOR MODULATORS<br/>[FR] MODULATEURS DES RECEPTEURS ESTROGENIQUES
  申请人：MERCK & CO INC

  公开号：WO2005051972A1

  公开（公告）日：2005-06-09

  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：骨质疏松、骨折、骨转移病、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、视网膜退行性疾病和癌症，尤其是乳腺、子宫和前列腺癌。
• Steroid Series. XVI. The Preparation of 3α, 5α-Cyclo-6β, 19-oxidosteroids and its Conversion to 19-Oxygenated Steroid Derivatives
  作者：Katsumi Tanabe、Rinji Takasaki、Kiyoshi Sakai、Ryozo Hayashi、Yasuhiro Morisawa、Teruo Hashimoto

  DOI：10.1248/cpb.15.15

  日期：——

  3α, 5α-Cyclo-6β, 19-oxidosteroid (II) was synthesized by the lead tetraacetate oxidation of 3α, 5α-cyclo-6β-hydroxysteroid (I) in benzene. The acid-catalysed solvolysis of the oxide (II) afforded 3α, 5α-cyclo-19-hydroxy-6β-substituted steroid (XVI) and/or Δ5-19-hydroxy-3β-substituted steroid (XVII), depending upon the reaction conditions employed. Oxidation of the oxide (II) with Jones reagent gave 3α, 5α-cyclo-6β, 19-dioxosteroid (XIX) with two equivalent molar oxidant, and 3α, 5α-cyclo-6-oxosteroid-19-oic acid (XX) with the excess reagent.

  3α, 5α-环-6β, 19-氧化类固醇(II)是通过四乙酸铅在苯中氧化3α, 5α-环-6β-羟基类固醇(I)合成的。氧化物(II)的酸催化溶剂解提供3α，5α-环-19-羟基-6β-取代的类固醇(XVI)和/或Δ5-19-羟基-3β-取代的类固醇(XVII)，取决于反应采用的条件。用琼斯试剂氧化氧化物(II)，得到3α，5α-环-6β，19-二氧类固醇(XIX)和两个当量摩尔氧化剂，以及3α，5α-环-6-氧类固醇-19-油酸(XX)多余的试剂。
• 19-Oxygenated-androst-5-enes for the enhancement of libido
  申请人：Richardson-Merrell Inc.

  公开号：US04139617A1

  公开（公告）日：1979-02-13

  The present invention concerns derivatives of 19-oxygenated-androst-5-enes which are useful in the enhancement of libido and related psychic attitudes.

  本发明涉及19-氧化睾酮-5-烯的衍生物，其可用于增强性欲和相关的心理态度。
• The hydroxylation of Δ5-androstenes by Cephalosporium aphidicola
  作者：Caroline M Bensasson、James R Hanson、A.Christy Hunter

  DOI：10.1016/s0031-9422(98)00312-4

  日期：1998.12

  Whereas the major hydroxylation product of 3 beta-hydroxy-5 alpha-androstan-17-one by Cephalosporium aphidicola is the 11 alpha-alcohol, the presence of a Delta(5)-double bond in the substrate leads to nonstereospecific allylic hydroxylation at C-7. Hydroxylation at C-11 became a minor transformation and there was no detectable hydroxylation at C-14. (C) 1998 Elsevier Science Ltd. All rights reserved.