19-nor-Δ^1,3,5(10)-cholestatrien-3-ol | 5918-28-5

• 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: 19-nor-Δ^1,3,5(10)-cholestatrien-3-ol
• 英文别名: 19-Norcholesta-1,3,5(10)-trien-3-ol；19-norcholesta-1,3,5(10)trien-3-ol；19-nor-cholesta-1,3,5(10)-trien-3-ol；3-Hydroxy-19-norcholesta-1,3,5(10)-triene；(8S,9S,13R,14S,17R)-13-methyl-17-[(2R)-6-methylheptan-2-yl]-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-ol
• CAS: 5918-28-5
• 化学式: C₂₆H₄₀O
• 分子量: 368.603
• InChiKey: HIGFJBWLJMUGFT-XTNBKHNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.77
• 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：

  19-nor-Δ^1,3,5(10)-cholestatrien-3-ol 在 乙酸酐 作用下， 以 吡啶 、 水 为溶剂， 生成 3-Acetoxy-19-nor-Δ^1,3,5(10)-cholestatrien
  参考文献：
  名称：

  Process for the preparation of 11-.beta.-nitro-oxysteroids

  摘要：

  制备含有芳香环A的9-α-羟基-11-β-硝基氧化甾体的过程，其中在硝酸根离子存在下，芳香环A-环含有的9,11-未取代类固醇或相应的9,11-去氢类固醇被氧化为偶氮离子。

  公开号：

  US03980681A1
• 作为产物：
  描述：

  3β-acetoxycholest-5-en-19-ol 在 lead(IV) acetate 、 盐酸 、 氢氧化钾 、 sodium hydroxide 、 jones' reagent 、 copper diacetate 作用下， 以 甲醇 、 乙醇 、 丙酮 、 甲苯 为溶剂， 反应 11.25h， 生成 19-nor-Δ^1,3,5(10)-cholestatrien-3-ol
  参考文献：
  名称：

  Sengupta, Pasupati; Sen, Manju; Sarkar, Arup, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 611 - 615

  摘要：

  DOI：

文献信息

• Aromatic steroids. Part III. Chromium trioxide oxidation of some 19-norcholesta-1,3,5(10)-trienes
  作者：R. C. Cambie、Valerie F. Carlisle、T. D. R. Manning

  DOI：10.1039/j39690001240

  日期：——

  Chromium trioxide oxidation of ring-A-substituted 19-norcholesta-1,3,5(10)-trienes gives results similar to those obtained for analogous oestra-1,3,5(10)-trienes. 3-Methoxy-19-norcholesta-1,3,5(10)-triene yields the 9β-hydroxy-11-oxo-derivative as the major product but introduction of a methyl group in the C-1 position blocks oxidation in the C-11 position. Oxidation of compounds with substituents

  环A-取代的19-降胆甾烯-1,3,5（10）-三烯的三氧化铬氧化得到的结果类似于类似的oestra-1,3,5（10）-三烯所获得的结果。3-Methoxy-19-norcholesta-1,3,5（10）-triene产生9β-hydroxy-11-oxo-derivatives作为主要产物，但在C-1位置引入甲基会阻止C中的氧化-11位。在C-3以外的位置带有取代基的化合物进行氧化，生成6-氧代衍生物作为主要产物。
• Stereoelectronically Controlled, Thallium(III)-Mediated C-19 Degradation of 19-Hydroxy Steroids. An Expedient Route to Estrone and its Congeners via 19-Nor-10.beta.-hydroxy Intermediates
  作者：Pavel Kocovsky、Richard S. Baines

  DOI：10.1021/jo00097a056

  日期：1994.9

  Estrone- (8b) has been synthesized in four steps from 3 beta-acetoxy-19-hydroxyandrost-5-en-17-one (2b), readily available from an industrial precursor. A key feature of the strategy is a stereoelectronically controlled, TI(III)-mediated degradation (2b --> 5b). Oppenauer oxidation of diol 6b, resulting from saponification of the acetate 5b, afforded the unsaturated 10 beta-hydroxy ketone 7b, acid treatment of which induced aromatization affording 8b. An alternative route including dehydration (5b --> 9b) followed by Oppenauer oxidation (10b --> 8b) gave comparable results. This strategy has first been developed with the aid of cholestane model compounds (2a --> 5a) and then successfully applied to the synthesis of analogues in the cholestane, androstane, and pregnane series to produce the corresponding 19-nor-10 beta-hydroxy derivatives 7a-d and A-aromatic steroids 8a-d.
• Suginome, Hiroshi; Senboku, Hisanori; Yamada, Shinji, Journal of the Chemical Society. Perkin transactions I, 1990, # 8, p. 2199 - 2205
  作者：Suginome, Hiroshi、Senboku, Hisanori、Yamada, Shinji

  DOI：——

  日期：——
• STEROIDS. X.¹ AROMATIZATION EXPERIMENTS IN THE CHOLESTEROL SERIES
  作者：J. ROMO、G. ROSENKRANZ、CARL DJERASSI

  DOI：10.1021/jo01152a027

  日期：1950.11
• SUGINOME, HIROSHI;SENBOKU, HISANORI;YAMADA, SHINJI, TETRAHEDRON LETT., 29,(1988) N 1, 79-80
  作者：SUGINOME, HIROSHI、SENBOKU, HISANORI、YAMADA, SHINJI

  DOI：——

  日期：——