3,3,17,17-(ethylenedioxy)-11β-hydroxymethyl-androst-5-ene | 885126-12-5

• 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: 3,3,17,17-(ethylenedioxy)-11β-hydroxymethyl-androst-5-ene
• CAS: 885126-12-5
• 化学式: C₂₄H₃₆O₅
• 分子量: 404.547
• InChiKey: CJZLTFJDCAPTBY-NWFSVNAMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  29
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,3,17,17-(ethylenedioxy)-11β-hydroxymethyl-androst-5-ene 在 三甲基氯硅烷 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 0.33h， 以100%的产率得到11β-hydroxymethyl-androst-4-ene-3,17-dione
  参考文献：
  名称：

  Synthesis of the 11β-hydroxymethyl-androst-4-en-3,17-dione

  摘要：

  The 11 beta-hydroxymethyl-androst-4-en-3,17-dione 5 was prepared within five synthetic steps starting from the commercially available adrenosterone with an overall yield of 24%. The 11-ketosteroid 1 was subjected to a Peterson methylenation. The subsequent hydroboration/oxidation sequence in position 11 was regio- and stereoselectively conducted using the borane-methyl sulfide complex at 0 degrees C. The target molecule was then obtained by deprotection using in situ generated TMSI. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.01.031
• 作为产物：
  描述：

  3,3,17,17-(ethylenedioxy)-11β-hydroxy-11α-(methyltrimethylsilyl)-androst-5-ene 在 硼烷四氢呋喃络合物 、 potassium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 9.0h， 生成 3,3,17,17-(ethylenedioxy)-11β-hydroxymethyl-androst-5-ene
  参考文献：
  名称：

  Synthesis of the 11β-hydroxymethyl-androst-4-en-3,17-dione

  摘要：

  The 11 beta-hydroxymethyl-androst-4-en-3,17-dione 5 was prepared within five synthetic steps starting from the commercially available adrenosterone with an overall yield of 24%. The 11-ketosteroid 1 was subjected to a Peterson methylenation. The subsequent hydroboration/oxidation sequence in position 11 was regio- and stereoselectively conducted using the borane-methyl sulfide complex at 0 degrees C. The target molecule was then obtained by deprotection using in situ generated TMSI. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.01.031

文献信息

• Synthesis of the 11β-hydroxymethyl-androst-4-en-3,17-dione
  作者：Elie Stéphan、Maude Brossat、Vincent Lecomte、Pierre-Antoine Bouit

  DOI：10.1016/j.tet.2006.01.031

  日期：2006.3

  The 11 beta-hydroxymethyl-androst-4-en-3,17-dione 5 was prepared within five synthetic steps starting from the commercially available adrenosterone with an overall yield of 24%. The 11-ketosteroid 1 was subjected to a Peterson methylenation. The subsequent hydroboration/oxidation sequence in position 11 was regio- and stereoselectively conducted using the borane-methyl sulfide complex at 0 degrees C. The target molecule was then obtained by deprotection using in situ generated TMSI. (c) 2006 Elsevier Ltd. All rights reserved.