(1R,2S,5R,6R,9R,13S)-5-methyl-6-[(2R)-6-methylheptan-2-yl]pentacyclo[11.8.0.02,10.05,9.015,20]henicosa-10,15,17,19-tetraene-14,21-dione | 188577-75-5

• 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: (1R,2S,5R,6R,9R,13S)-5-methyl-6-[(2R)-6-methylheptan-2-yl]pentacyclo[11.8.0.02,10.05,9.015,20]henicosa-10,15,17,19-tetraene-14,21-dione
• CAS: 188577-75-5
• 化学式: C₃₀H₄₀O₂
• 分子量: 432.646
• InChiKey: AINNUQXYFFUYOS-YDZBWXALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2S,5R,6R,9R,13S)-5-methyl-6-[(2R)-6-methylheptan-2-yl]pentacyclo[11.8.0.02,10.05,9.015,20]henicosa-10,15,17,19-tetraene-14,21-dione 在 氧气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以90%的产率得到(5R,6R,9R)-5-methyl-6-[(2R)-6-methylheptan-2-yl]pentacyclo[11.8.0.02,10.05,9.015,20]henicosa-1(13),2(10),11,15,17,19-hexaene-14,21-dione
  参考文献：
  名称：

  Synthesis and cytotoxic activity of steroid-anthraquinone hybrids

  摘要：

  Synthesis of cytotoxic steroidal derivatives containing a quinone moiety is described. The synthetic strategy is based on an unsual A + CD --> ABCD Diels-Alder approach which generates 9 beta-H cholestane analogs. The adducts formed are efficiently aromatized in basic media to give steroid-anthaquinones hybrids showing interesting cytotoxic activity on four tumor cell lines. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00693-5
• 作为产物：
  描述：

  维生素 D3 在 lead(IV) acetate 、 potassium permanganate 、 四(三苯基膦)钯 、 sodium hexamethyldisilazane 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 3.0h， 生成 (1R,2S,5R,6R,9R,13S)-5-methyl-6-[(2R)-6-methylheptan-2-yl]pentacyclo[11.8.0.02,10.05,9.015,20]henicosa-10,15,17,19-tetraene-14,21-dione
  参考文献：
  名称：

  Synthesis and cytotoxic activity of steroid-anthraquinone hybrids

  摘要：

  Synthesis of cytotoxic steroidal derivatives containing a quinone moiety is described. The synthetic strategy is based on an unsual A + CD --> ABCD Diels-Alder approach which generates 9 beta-H cholestane analogs. The adducts formed are efficiently aromatized in basic media to give steroid-anthaquinones hybrids showing interesting cytotoxic activity on four tumor cell lines. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00693-5

文献信息

• Synthesis of unusual cholestane analogs by Diels-Alder reaction (A+CD → ABCD)
  作者：Francesco De Riccardis、Irene Izzo、Consiglia Tedesco、Guido Sodano

  DOI：10.1016/s0040-4039(97)00270-0

  日期：1997.3

  Unprecedented cholestane analogs have been synthesized by Diels-Alder reactions between a diene generated in high yields from vitamin D-3 and appropriate dienophiles. This strategy is useful for the scarcely utilized A+CD --> ABCD approach to the tetracyclic steroid nucleus. (C) 1997 Published by Elsevier Science Ltd.
• Synthesis and cytotoxic activity of steroid-anthraquinone hybrids
  作者：Francesco De Riccardis、Irene Izzo、Marcello Di Filippo、Guido Sodano、Fulvio D'Acquisto、Rosa Carnuccio

  DOI：10.1016/s0040-4020(97)00693-5

  日期：1997.8

  Synthesis of cytotoxic steroidal derivatives containing a quinone moiety is described. The synthetic strategy is based on an unsual A + CD --> ABCD Diels-Alder approach which generates 9 beta-H cholestane analogs. The adducts formed are efficiently aromatized in basic media to give steroid-anthaquinones hybrids showing interesting cytotoxic activity on four tumor cell lines. (C) 1997 Elsevier Science Ltd.