[(1'S,2'R,5'S,11'R,12'S,16'S)-2',16'-dimethylspiro[1,3-dioxolane-2,15'-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadecane]-5'-yl] acetate | 115350-45-3

• 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: [(1'S,2'R,5'S,11'R,12'S,16'S)-2',16'-dimethylspiro[1,3-dioxolane-2,15'-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadecane]-5'-yl] acetate
• CAS: 115350-45-3；115350-46-4
• 化学式: C₂₃H₃₄O₅
• 分子量: 390.52
• InChiKey: PGUJPWFAGXPGHW-OYKMYEKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.84
• 重原子数：
  28.0
• 可旋转键数：
  1.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  57.29
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  [(1'S,2'R,5'S,11'R,12'S,16'S)-2',16'-dimethylspiro[1,3-dioxolane-2,15'-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadecane]-5'-yl] acetate 在 吡啶 、 chromium(VI) oxide 、 氢氧化钾 、 氯化亚砜 作用下， 以 甲醇 、 丁酮 为溶剂， 生成 3-羟基雄甾-4-烯-6,17-二酮
  参考文献：
  名称：

  Synthesis of Cytotoxic 6E-Hydroximino-4-ene Steroids:  Structure/Activity Studies

  摘要：

  In an effort to determine the pharmaceutical utility and the structural requirements for activity against various tumor cell lines, several 6E-hydroximino-4-ene steroids with different side chains and degrees of unsaturation on ring A were synthesized in our laboratory. Evaluation of the synthesized compounds for cytotoxicity against P-388, A-549, HT-29, and MEL-28 tumor cells revealed that some important structural features are required for activity. The presence of a cholesterol-type side chain, which appears to play a major role in determining the biological activity, the existence of a ketone functionality at C-3, and an elevated degree of oxidation on ring A all result in higher bioactivity than other structural motifs.

  DOI：

  10.1021/jm010867n
• 作为产物：
  描述：

  去氢表雄酮 在 吡啶 、 己二酸 、 间氯过氧苯甲酸 作用下， 以 氯仿 、 苯 为溶剂， 反应 28.0h， 生成 [(1'S,2'R,5'S,11'R,12'S,16'S)-2',16'-dimethylspiro[1,3-dioxolane-2,15'-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadecane]-5'-yl] acetate
  参考文献：
  名称：

  Synthesis of Cytotoxic 6E-Hydroximino-4-ene Steroids:  Structure/Activity Studies

  摘要：

  In an effort to determine the pharmaceutical utility and the structural requirements for activity against various tumor cell lines, several 6E-hydroximino-4-ene steroids with different side chains and degrees of unsaturation on ring A were synthesized in our laboratory. Evaluation of the synthesized compounds for cytotoxicity against P-388, A-549, HT-29, and MEL-28 tumor cells revealed that some important structural features are required for activity. The presence of a cholesterol-type side chain, which appears to play a major role in determining the biological activity, the existence of a ketone functionality at C-3, and an elevated degree of oxidation on ring A all result in higher bioactivity than other structural motifs.

  DOI：

  10.1021/jm010867n

文献信息

• Synthesis of unsaturated carbonyl compounds via a chromium-mediated allylic oxidation by 70% tert.butylhydroperoxide
  作者：Jacques Muzart

  DOI：10.1016/s0040-4039(00)96591-2

  日期：1987.1

  Alkenes were converted into α,β-unsaturated carbonyl compounds using excess of tert.butylhydroperoxide and catalytic amounts of chromiumVI oxide at room temperature. Fair yields and conversions were obtained from Δ5-steroids while allylic oxidation of acyclic alkenes was less efficient. Epoxidation of the double bond, sometimes observed, remained a minor reaction pathway.

  烯烃转化成使用过量tert.butylhydroperoxide和催化量的铬的α，β不饱和羰基化合物VI在室温下的氧化。公平的产率和转化率从Δ得到5而无环烯烃的烯丙基氧化是效率较低-steroids。有时观察到双键的环氧化仍然是次要的反应途径。
• MUZART, JACQUES, TETRAHEDRON LETT., 28,(1987) N 40, 4665-4668
  作者：MUZART, JACQUES

  DOI：——

  日期：——