3-(tetrahydropyran-2'-yloxy)-17β-(N-2-chloroethyl-N'-nitrosoureyl)-1,3,5(10)-estratrien-17α-carbonitrile | 81912-63-2

• 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
• 英文名称: 3-(tetrahydropyran-2'-yloxy)-17β-(N-2-chloroethyl-N'-nitrosoureyl)-1,3,5(10)-estratrien-17α-carbonitrile
• CAS: 81912-63-2
• 化学式: C₂₇H₃₅ClN₄O₄
• 分子量: 515.052
• InChiKey: PBRVJQPQWRCWFU-ASFDUXSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.64
• 重原子数：
  36.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  104.02
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3-(tetrahydropyran-2'-yloxy)-17β-(N-2-chloroethyl-N'-nitrosoureyl)-1,3,5(10)-estratrien-17α-carbonitrile 在 Amberlite IR 120 (H+ form) 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以85%的产率得到3-hydroxy-17β-(N-2-chloroethyl-N'-nitrosoureyl)-1,3,5(10)-estratrien-17α-carbonitrile
  参考文献：
  名称：

  New steroidal nitrosoureas

  摘要：

  Reformatsky reaction of 3beta, 21-diacyloxy-and 3beta-methoxy-21-acyloxy-5-pregnen-20-one with ethyl bromoacetate yields, through an intramolecular 1,2-acyl migration, 38, 20 XI-diacyloxy- and 3 beta-methoxy-20 XI-acyloxy-14alpha-card-5-enolide respectively. The 20 XI-acyloxy-14, alpha-card-5-enolides were converted into the respective 20 XI-hydroxy-14alpha-card-5-enolides and the 14 alpha card-5,20(22)-dienolides. Experimental support to the proposed intramolecular 1,2-acyl migration is provided by the use of labelled compounds.

  DOI：

  10.1016/0039-128x(82)90081-2
• 作为产物：
  描述：

  在 亚硝酰氯 作用下， 以 吡啶 、 氯仿 为溶剂， 生成 3-(tetrahydropyran-2'-yloxy)-17β-(N-2-chloroethyl-N'-nitrosoureyl)-1,3,5(10)-estratrien-17α-carbonitrile
  参考文献：
  名称：

  New steroidal nitrosoureas

  摘要：

  Reformatsky reaction of 3beta, 21-diacyloxy-and 3beta-methoxy-21-acyloxy-5-pregnen-20-one with ethyl bromoacetate yields, through an intramolecular 1,2-acyl migration, 38, 20 XI-diacyloxy- and 3 beta-methoxy-20 XI-acyloxy-14alpha-card-5-enolide respectively. The 20 XI-acyloxy-14, alpha-card-5-enolides were converted into the respective 20 XI-hydroxy-14alpha-card-5-enolides and the 14 alpha card-5,20(22)-dienolides. Experimental support to the proposed intramolecular 1,2-acyl migration is provided by the use of labelled compounds.

  DOI：

  10.1016/0039-128x(82)90081-2