| 182262-22-2

• 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
• CAS: 182262-22-2
• 化学式: C₃₆H₅₆O₅S
• 分子量: 600.904
• InChiKey: JOTLMHPLNPNKRB-WZXBEDRISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.22
• 重原子数：
  42.0
• 可旋转键数：
  8.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  72.83
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  在 碘苯二乙酸 、 碘 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 0.33h， 生成 methyl 2-[(3R,3aR,5aS,6S,7S,9aR,9bS)-6-[[(3S,5R)-5-(benzenesulfonylmethyl)dioxolan-3-yl]methyl]-3a,6-dimethyl-3-[(2R)-6-methylheptan-2-yl]-2,3,4,5,5a,7,8,9,9a,9b-decahydro-1H-cyclopenta[a]naphthalen-7-yl]acetate
  参考文献：
  名称：

  Stereospecific Synthesis of 1,2-Dioxolanes by Alkoxy Radical β-Fragmentation of Steroidal Cyclic Peroxyhemiacetals

  摘要：

  A new one-pot synthesis of 3,5-substituted 1,2-dioxolanes from six-membered cyclic peroxyhemiacetal derivatives of hexahydrobenzo[c][1,2]dioxin-8a-ol is described. A number of steroidal peroxyhemiacetals, (2S,2'S,3R)-(11), (2S,2'R,3R/S)-(13), (2R,2'R,3R/S)-2-(2'-hydroperoxypropyl-3'-phenylsulfonyl)-5 alpha-cholestan-3-one 2',3-peroxyhemiacetal (17), and (2S,5R)-2-hydroperoxy-3-phenylsulfonyl-4-nor-3,4-secocholestan-5-one 2,5-peroxyhemiacetal (24), have been prepared in order to test the scope and diastereoselectivity of the present methodology. These substrates were irradiated with visible light in the presence of (diacetoxyiodo)benzene and iodine to generate the corresponding alkoxy radical, which undergoes regioselective beta-fission yielding a carbon radical, that further reacts in a stereoselective manner with an iodine atom to give a 10-membered peroxylactone. This iodide intermediate is intramolecularly substituted by the peroxide anion generated by intermolecular nucleophilic attack of a hydroxide or methoxide anion to-the acyl carbon with concomitant carbon-oxygen bond cleavage. This operationally simple reaction permitted us to synthesize methyl (2S,2'S)-(33), (2S,2'R)-(34), (2R,2'R)-1-[5'-[(phenylsulfonyl)methyl]-[1',2']dioxolan-3'yl]-2-nor-2,3-secocholestan-3-oate (36) and methyl (1'R,1'''R,3'aS,3 " R,4'S,5'S,5 " S, 7'aR)-3-[5'-[5 "-(phenylsulfonyl)methyl]-3 "-methyl[1 ",2 "]dioxolan-3 "-yl]-1'-(1''',5'''-dimethylhexyl)-7'a-methyloctahydroinden-4'-yl]propanoate (37) in good yields.

  DOI：

  10.1021/jo980319q
• 作为产物：
  描述：

  在 间氯过氧苯甲酸 作用下， 生成
  参考文献：
  名称：

  过氧半缩醛的断裂。1,2-二氧戊环的立体选择性合成

  摘要：

  描述了一种在温和条件下通过将易得的过氧半缩醛中的烷氧基进行β-片段化来合成1,2-二氧戊环的新有效方法。自由基反应以非对映选择性的方式进行，提供了唯一的1,2-二氧戊环。

  DOI：

  10.1016/0040-4039(96)01360-3