(-)-norfluorocurarine hydrochloride | 17682-63-2

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 马钱子生物碱
• 英文名称: (-)-norfluorocurarine hydrochloride
• 英文别名: (3aS,5S,11bR,E)-12-ethylidene-1,2,3a,4,5,7-hexahydro-3,5-ethanopyrrolo[2,3-d]carbazole-6-carbaldehyde hydrochloride；(1R,11S,12E,17S)-12-ethylidene-8,14-diazapentacyclo[9.5.2.01,9.02,7.014,17]octadeca-2,4,6,9-tetraene-10-carbaldehyde;hydrochloride
• CAS: 17682-63-2
• 化学式: C₁₉H₂₀N₂O*ClH
• 分子量: 328.842
• InChiKey: YNWGTNNDSWZYCO-BJBGRGONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.28
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (-)-norfluorocurarine hydrochloride 在 盐酸 、 hydroxylamine sulfate 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 反应 0.33h， 生成 16-cyanonorfluorocurarine hydrochloride
  参考文献：
  名称：

  Syntheses based on norfluorocurarine. 4. Reactions with hydroxylamine

  摘要：

  Transformation products of the alkaloid (–)-norfluorocurarine with hydroxylamine were studied. The oxime of norfluorocurarine was obtained and converted by treatment with EtOH into 2-hydroxy-16-cyano-2,16dihydronorfluorocurarine. The structures of 2-hydroxy-16-cyano-2,16-dihydronorfluorocurarine and 16-cyanonorfluorocurarine hydrochloride were established by XSA and NMR spectroscopy. The absolute structure of 2-hydroxy-16-cyano-2,16-dihydronorfluorocurarine was established and enabled the configurations of the asymmetric centers to be determined as 2R, 3S, 7R, 15S, and 16R.

  DOI：

  10.1007/s10600-012-0165-9

文献信息

• Syntheses based on norfluorocurarine. 6. Reaction with phenylhydrazine
  作者：B. Tashkhodzhaev、M. M. Mirzaeva、P. Kh. Yuldashev

  DOI：10.1007/s10600-012-0328-8

  日期：2012.9

  The indole alkaloid norfluorocurarine was reacted with phenylhydrazine. An x-ray crystal structure analysis found that the phenylhydrazine was bonded through its N atoms to C2 and C17 and that the N1–C2 bond of the indole core was cleaved to form an NH2 group and a water molecule was released.

  吲哚生物碱诺氟脲与苯肼发生了反应。X 射线晶体结构分析发现，苯肼通过其 N 原子与 C2 和 C17 结合，吲哚核心的 N1-C2 键被裂解，形成一个 NH2 基团，并释放出一个水分子。
• Syntheses based on norfluorocurarine. 4. Reactions with hydroxylamine
  作者：M. M. Mirzaeva、B. Tashkhodzhaev、M. G. Levkovich、A. G. Eshimbetov、P. Kh. Yuldashev、N. D. Abdullaev

  DOI：10.1007/s10600-012-0165-9

  日期：2012.3

  Transformation products of the alkaloid (–)-norfluorocurarine with hydroxylamine were studied. The oxime of norfluorocurarine was obtained and converted by treatment with EtOH into 2-hydroxy-16-cyano-2,16dihydronorfluorocurarine. The structures of 2-hydroxy-16-cyano-2,16-dihydronorfluorocurarine and 16-cyanonorfluorocurarine hydrochloride were established by XSA and NMR spectroscopy. The absolute structure of 2-hydroxy-16-cyano-2,16-dihydronorfluorocurarine was established and enabled the configurations of the asymmetric centers to be determined as 2R, 3S, 7R, 15S, and 16R.