19-nor-Δ^1(10),5-cholestadien-3β-ol | 115375-50-3

• 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(10),5-cholestadien-3β-ol
• 英文别名: 19-Norcholesta-1(10),5-dien-3β-ol；3β-Hydroxycholesta-1(10),5-diene；(3S,8S,9S,13R,14S,17R)-13-methyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-ol
• CAS: 115375-50-3
• 化学式: C₂₆H₄₂O
• 分子量: 370.619
• InChiKey: VSWMOCXQIVUXBQ-XWLGQTROSA-N

物化性质

• 熔点：
  69.5-71.5 °C(Solvent: Methanol)
• 沸点：
  498.4±14.0 °C(predicted)
• 密度：
  1.00±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.92
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  19-nor-Δ^1(10),5-cholestadien-3β-ol 生成 (8R,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
  参考文献：
  名称：

  SUGINOME, HIROSHI;SENBOKU, HISANORI;YAMADA, SHINJI, J. CHEM. SOC. PERKIN TRANS. PT 1,(1990) N, C. 2199-2205

  摘要：

  DOI：
• 作为产物：
  描述：

  3β-acetoxycholest-5-en-19-ol 在 lead(IV) acetate 、 盐酸 、 氢氧化钾 、 copper diacetate 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 10.0h， 生成 19-nor-Δ^1(10),5-cholestadien-3β-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

• 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：——
• SUGINOME, HIROSHI;SENBOKU, HISANORI;YAMADA, SHINJI, J. CHEM. SOC. PERKIN TRANS. PT 1,(1990) N, C. 2199-2205
  作者：SUGINOME, HIROSHI、SENBOKU, HISANORI、YAMADA, SHINJI

  DOI：——

  日期：——
• 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：——
• SENGUPTA, PASUPATI;SEN, MANJU;SARKAR, ARUP;DAS, SAKTIPADA, INDIAN J. CHEM., 26,(1987) N 7, 611-615
  作者：SENGUPTA, PASUPATI、SEN, MANJU、SARKAR, ARUP、DAS, SAKTIPADA

  DOI：——

  日期：——