3,3,17,17-(ethylenedioxy)-11-methylidene-androst-5-ene | 691851-05-5

• 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)-11-methylidene-androst-5-ene
• 英文别名: 11-methylidene-3,3:17,17-bis(ethylenedioxy)androst-5-ene
• CAS: 691851-05-5
• 化学式: C₂₄H₃₄O₄
• 分子量: 386.532
• InChiKey: JDRXJCFODRVGKX-YFNVTMOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  28
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,3,17,17-(ethylenedioxy)-11-methylidene-androst-5-ene 在 三甲基氯硅烷 、 硼烷四氢呋喃络合物 、 sodium iodide 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 7.33h， 生成 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-bis-ethanediyldioxy-11α-methyl-androst-5-en-11β-ol 在 正丁基锂 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 4.58h， 生成 3,3,17,17-(ethylenedioxy)-11-methylidene-androst-5-ene
  参考文献：
  名称：

  多种受阻草酸酯用于立体选择性制备新型11修饰的Androst-5-ene衍生物

  摘要：

  使用高度受阻的11β-羟基雄烯基-5-烯的草酸酯衍生物可生产11α和11β改性的雄烯基5-烯衍生物3a，b以及环外和内环脱水化合物4a - c和5b - c。1a - c。通过在自由基条件下通过分子内5-exo环化由相应的草酸酯作为前体，首次以良好的非对映选择性生产11-四氢呋喃衍生物6。

  DOI：

  10.1021/jo0401016

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.
• Versatile Use of Hindered Oxalates for the Stereoselective Preparation of Novel 11-Modified Androst-5-ene Derivatives
  作者：Vincent Lecomte、Elie Stéphan、Marie-Noelle Rager、Gérard Jaouen

  DOI：10.1021/jo0401016

  日期：2004.4.1

  The 11α- and 11β-modified androst-5-ene derivatives 3a,b as well as the exo- and endocyclic dehydrated compounds 4a−c and 5b−c were produced using the oxalate derivatives of the highly hindered 11β-hydroxyandrost-5-enes 1a−c. The 11-tetrahydrofuran derivative 6 was produced for the first time with good diastereoselectivity by an intramolecular 5-exo cyclization under radical conditions from the corresponding

  使用高度受阻的11β-羟基雄烯基-5-烯的草酸酯衍生物可生产11α和11β改性的雄烯基5-烯衍生物3a，b以及环外和内环脱水化合物4a - c和5b - c。1a - c。通过在自由基条件下通过分子内5-exo环化由相应的草酸酯作为前体，首次以良好的非对映选择性生产11-四氢呋喃衍生物6。