3'-methylspiro[androsta-1,4-dien-3,2'(3'H)benzothiazol]-9(11),16-dien-17-nitrile

• 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'-methylspiro[androsta-1,4-dien-3,2'(3'H)benzothiazol]-9(11),16-dien-17-nitrile
• 英文别名: (8'S,10'S,13'S,14'S)-3,10',13'-trimethylspiro[1,3-benzothiazole-2,3'-6,7,8,12,14,15-hexahydrocyclopenta[a]phenanthrene]-17'-carbonitrile
• 化学式: C₂₇H₂₈N₂S
• 分子量: 412.599
• InChiKey: ASWADCMRQNIIRX-AUQHFYNSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  30
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3'-methylspiro[androsta-1,4-dien-3,2'(3'H)benzothiazol]-9(11),16-dien-17-nitrile 、 乙烯基乙醚 在 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以88%的产率得到17-cyanoandrosta-1,4,9(11),16-tetraen-3-one
  参考文献：
  名称：

  A concise effective deprotection of spiro 3-cyclic thiaza ketal of steroidal 1,4-dien-3-one

  摘要：

  An effective deprotective method of spiro 3-cyclic thiaza ketal of steroidal 1,4-dien-3-ones using alkyl vinyl ether in the presence of protic acid followed by the treatment of aqueous alkali was described. This novel protocol could be fulfilled under mild condition with high yield. The mechanism mediated by a carbonium ion formed in situ was clarified by the capture of the cleaved fragment. (c) 2006 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2006.10.008
• 作为产物：
  描述：

  17-cyanoandrosta-1,4,9(11),16-tetraen-3-one 、 2-(甲基氨基)苯硫酚 在 三氟化硼乙醚 作用下， 以 氯仿 为溶剂， 反应 7.0h， 以57%的产率得到3'-methylspiro[androsta-1,4-dien-3,2'(3'H)benzothiazol]-9(11),16-dien-17-nitrile
  参考文献：
  名称：

  A concise effective deprotection of spiro 3-cyclic thiaza ketal of steroidal 1,4-dien-3-one

  摘要：

  An effective deprotective method of spiro 3-cyclic thiaza ketal of steroidal 1,4-dien-3-ones using alkyl vinyl ether in the presence of protic acid followed by the treatment of aqueous alkali was described. This novel protocol could be fulfilled under mild condition with high yield. The mechanism mediated by a carbonium ion formed in situ was clarified by the capture of the cleaved fragment. (c) 2006 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2006.10.008

文献信息

• A concise effective deprotection of spiro 3-cyclic thiaza ketal of steroidal 1,4-dien-3-one
  作者：Bei Na Zhang、Ying Chen、Qian Zhang、Peng Xia

  DOI：10.1016/j.steroids.2006.10.008

  日期：2007.1

  An effective deprotective method of spiro 3-cyclic thiaza ketal of steroidal 1,4-dien-3-ones using alkyl vinyl ether in the presence of protic acid followed by the treatment of aqueous alkali was described. This novel protocol could be fulfilled under mild condition with high yield. The mechanism mediated by a carbonium ion formed in situ was clarified by the capture of the cleaved fragment. (c) 2006 Elsevier Inc. All rights reserved.