[(3R,8R,9S,10R,13S,14S)-10,13-dimethyl-5'-methylidene-2'-oxospiro[1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-17,4'-1,3-dioxolane]-3-yl] acetate | 1138342-45-6

• 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: [(3R,8R,9S,10R,13S,14S)-10,13-dimethyl-5'-methylidene-2'-oxospiro[1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-17,4'-1,3-dioxolane]-3-yl] acetate
• CAS: 1138342-45-6
• 化学式: C₂₄H₃₂O₅
• 分子量: 400.515
• InChiKey: OYABJLANBLWMGO-YKTYGZJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  Acetic acid (3R,8R,9S,10R,13S,14S,17R)-17-tert-butoxycarbonyloxy-17-ethynyl-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 在 三苯基膦双(三氟甲磺酰亚胺)金 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以90%的产率得到[(3R,8R,9S,10R,13S,14S)-10,13-dimethyl-5'-methylidene-2'-oxospiro[1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-17,4'-1,3-dioxolane]-3-yl] acetate
  参考文献：
  名称：

  Gold-catalyzed rearrangement of propargylic tert-butyl carbonates

  摘要：

  Diversely substituted 4-alkylidene-1,3-dioxolan-2-ones are efficiently synthesized by a gold(I)-catalyzed rearrangement of propargylic tert-butyl carbonates. The substrates are readily accessible and the transformation, which is performed under mild reaction conditions using a low loading of catalyst, allows the synthesis of cyclic carbonates, which would be less efficiently obtained using traditional methods. This procedure has also been applied to the stereoselective synthesis of (E)- or (Z)-4-halomethylene-1,3-dioxolan-2-ones, which Proved to be suitable substrates for palladium-catalyzed cross-coupling reactions. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.11.108