13α-isocyanato-3-methoxy-16,17-seco-17-nor-estra-1,3,5(10)-triene-16-nitrile | 625821-25-2

• 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: 13α-isocyanato-3-methoxy-16,17-seco-17-nor-estra-1,3,5(10)-triene-16-nitrile
• 英文别名: 2-[(1S,2S,4aS,10aR)-2-isocyanato-7-methoxy-2-methyl-3,4,4a,9,10,10a-hexahydro-1H-phenanthren-1-yl]acetonitrile
• CAS: 625821-25-2
• 化学式: C₁₉H₂₂N₂O₂
• 分子量: 310.396
• InChiKey: XPQMMJRGLXFVIO-YRXWBPOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  62.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  13α-isocyanato-3-methoxy-16,17-seco-17-nor-estra-1,3,5(10)-triene-16-nitrile 在 氢溴酸 、 sodium hydroxide 作用下， 以93%的产率得到13α-amino-3-methoxy-16,17-seco-17-nor-estra-1,3,5(10)-triene-16-nitrile
  参考文献：
  名称：

  Synthesis of 16,17-seco-steroids with iminomethyl-2-pyridine and aminomethylene-2-pyridine structures as chiral ligands for copper ions and molecular oxygen activation

  摘要：

  Starting from 16-oximino-3-methoxy-estra-1,3,5(10)-trien-17-one, the 16,17-seco-13alpha-carbaldehyde with a 16-nitrile function and its corresponding carboxylic acid have been synthesized via a Beckmann fragmentation. The corresponding 13alpha-amine is available by Curtius degradation of the carboxylic acid. Condensation of the carboxaldehyde with 2(aminomethyl)pyridine and the primary amine with pyridine-2-carboxaldehyde gave the corresponding iminomethyl-2-pyridine and the aminomethylene-2-pyridine compounds. Copper-mediated ligand hydroxylations with molecular oxygen were not successful. Reasons for this are discussed. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00539-1
• 作为产物：
  描述：

  3-methoxyestra-1,3,5(10)-triene-16,17-dione 16-oxime 在 吡啶 、 chromium(VI) oxide 、 sodium tetrahydroborate 、 硫酸 、 二苯基膦叠氮化物 、 三乙胺 、 对甲苯磺酰氯 作用下， 以 甲醇 、 丙酮 、 甲苯 为溶剂， 反应 3.83h， 生成 13α-isocyanato-3-methoxy-16,17-seco-17-nor-estra-1,3,5(10)-triene-16-nitrile
  参考文献：
  名称：

  Synthesis of 16,17-seco-steroids with iminomethyl-2-pyridine and aminomethylene-2-pyridine structures as chiral ligands for copper ions and molecular oxygen activation

  摘要：

  Starting from 16-oximino-3-methoxy-estra-1,3,5(10)-trien-17-one, the 16,17-seco-13alpha-carbaldehyde with a 16-nitrile function and its corresponding carboxylic acid have been synthesized via a Beckmann fragmentation. The corresponding 13alpha-amine is available by Curtius degradation of the carboxylic acid. Condensation of the carboxaldehyde with 2(aminomethyl)pyridine and the primary amine with pyridine-2-carboxaldehyde gave the corresponding iminomethyl-2-pyridine and the aminomethylene-2-pyridine compounds. Copper-mediated ligand hydroxylations with molecular oxygen were not successful. Reasons for this are discussed. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00539-1

文献信息

• Synthesis of 16,17-seco-steroids with iminomethyl-2-pyridine and aminomethylene-2-pyridine structures as chiral ligands for copper ions and molecular oxygen activation
  作者：Angéla Magyar、Bruno Schönecker、János Wölfling、Gyula Schneider、Wolfgang Günther、Helmar Görls

  DOI：10.1016/s0957-4166(03)00539-1

  日期：2003.9

  Starting from 16-oximino-3-methoxy-estra-1,3,5(10)-trien-17-one, the 16,17-seco-13alpha-carbaldehyde with a 16-nitrile function and its corresponding carboxylic acid have been synthesized via a Beckmann fragmentation. The corresponding 13alpha-amine is available by Curtius degradation of the carboxylic acid. Condensation of the carboxaldehyde with 2(aminomethyl)pyridine and the primary amine with pyridine-2-carboxaldehyde gave the corresponding iminomethyl-2-pyridine and the aminomethylene-2-pyridine compounds. Copper-mediated ligand hydroxylations with molecular oxygen were not successful. Reasons for this are discussed. (C) 2003 Elsevier Ltd. All rights reserved.