19-norcholest-5-ene-3β,10β-diol 3-monoacetate | 129921-73-9

• 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-norcholest-5-ene-3β,10β-diol 3-monoacetate
• 英文别名: 3β-acetoxy-19-oxacholest-5-ene；[(3S,8S,9S,10S,13R,14S,17R)-10-hydroxy-13-methyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 129921-73-9
• 化学式: C₂₈H₄₆O₃
• 分子量: 430.671
• InChiKey: SXTSKLAZAUJHBO-HHMDLNJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  19-norcholest-5-ene-3β,10β-diol 3-monoacetate 在 potassium carbonate 、 对甲苯磺酸 作用下， 以 1,4-二氧六环 、 甲醇 、 氯仿 、 水 为溶剂， 反应 0.25h， 生成 19-nor-Δ^1(10),5-cholestadien-3β-ol
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1021/jo00097a056
• 作为产物：
  描述：

  3β-acetoxycholest-5-en-19-ol 在 thallium(I) nitrate 作用下， 以 乙二醇二甲醚 为溶剂， 反应 81.0h， 生成 19-norcholest-5-ene-3β,10β-diol 3-monoacetate
  参考文献：
  名称：

  al（III）介导的不饱和醇环化的结构要求。产生19-降糖甾体的新型片段化反应

  摘要：

  不饱和醇（1）容易通过by（III）环化为羟基四氢呋喃（3），而已发现其同系物（4）作为新颖的，立体电子控制的裂解产物（7）；讨论了串联亲电环化/溶剂分解的范围；（7）的结构已经通过X射线晶体学确定。

  DOI：

  10.1039/c39900001026

文献信息

• Structural requirements for the thallium(<scp>III</scp>)-mediated cyclisation of unsaturated alcohols. A novel fragmentation reaction producing 19-norsteroids
  作者：Pavel KočOvský、Vratislav Langer、Adolf Gogoll

  DOI：10.1039/c39900001026

  日期：——

  The unsaturated alcohol (1) is readily cyclised to the hydroxytetrahydrofuran (3) by means of thallium(III), whereas its congener (4) has been found to give (7) as the product of a novel, stereoelectronically controlled, fragmentation; the scope of the tandem electrophilic cyclisation/solvolysis is discussed; the structure of (7) has been determined by X-ray crystallography.

  不饱和醇（1）容易通过by（III）环化为羟基四氢呋喃（3），而已发现其同系物（4）作为新颖的，立体电子控制的裂解产物（7）；讨论了串联亲电环化/溶剂分解的范围；（7）的结构已经通过X射线晶体学确定。
• Aminoalkyl steroids
  申请人：G. D. Searle & Co.

  公开号：US04495102A1

  公开（公告）日：1985-01-22

  Compounds of Formula I and II are useful as potent antiarrythmic agents without significant effect on cardiac output and blood pressure.

  公式I和II的化合物是有用的强效抗心律失常剂，不会对心输出量和血压产生显著影响。
• KOCOVSKY, PAVEL;POUR, MILAN, J. ORG. CHEM., 55,(1990) N1, C. 5580-5589
  作者：KOCOVSKY, PAVEL、POUR, MILAN

  DOI：——

  日期：——
• US4495102A
  申请人：——

  公开号：US4495102A

  公开（公告）日：1985-01-22
• 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.