3β-acetoxy-5-solanidene | 4216-84-6

• 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: 3β-acetoxy-5-solanidene
• 英文别名: 3β-Acetoxysolanidin；Solanidin-acetat；3β-acetoxy-solanid-5-ene；3β-Acetoxy-solanid-5-en；Acetylsolanidine；[(1S,2S,7S,10R,11S,14S,15R,16S,17R,20S,23S)-10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.02,11.05,10.015,23.017,22]tetracos-4-en-7-yl] acetate
• CAS: 4216-84-6
• 化学式: C₂₉H₄₅NO₂
• 分子量: 439.682
• InChiKey: ACTKMOYQUXATDV-XAKLIMFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  32
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3β-acetoxy-5-solanidene 在 chromium(VI) oxide 、 溶剂黄146 作用下， 生成 3β-acetoxy-solanid-5-en-7-one
  参考文献：
  名称：

  Die Darstellung von 7-Dehydro-solanidin (VII. Mitteilung) Mit 7 Abbildungen

  摘要：

  DOI：

  10.1002/ardp.19522850102
• 作为产物：
  描述：

  3β-hydroxy-18,28-cyclo-solanid-5-enium; iodide 在 吡啶 、 乙醇 、 sodium 作用下， 生成 3β-acetoxy-5-solanidene
  参考文献：
  名称：

  The Veratrine Alkaloids. XXXVII. The Structure of Isorubijervine. Conversion to Solanidine

  摘要：

  DOI：

  10.1021/ja01114a014

文献信息

• Improved Methods for Obtaining Immonium Perchlorates and Enamines of Solanidine Type Steroidal Alkaloids
  作者：Katarina M. Penov Gaši、Dušica Rackov Čolic、Otto N. Arcson、Zvonimir O. Sakač、Evgenija A. Djurendić、Marija N. Sakač、Ljubica Medic-Mijačevic、Dušan A. Miljković

  DOI：10.1135/cccc19961655

  日期：——

  Oxidation of solanidine and some of its derivatives with mercury(II) acetate in acetone afforded corresponding N-22 immonium perchlorates or 22(23)-enamines. It has been found that the effect of solvents on regioselectivity e.g. formation N-22 and N-16 immonium salts, was remarkable. The isomerisation of 22(23)-enamines into corresponding 20(22)-enamines, potentialy important intermediates in planned chemical degradation of solanidine to steroidal hormones, was performed in 0.1% acetic acid in ether, or in dichloromethane (chloroform).

  在丙酮中，用醋酸汞氧化茄碱和其一些衍生物，得到相应的N-22免疫过氯酸盐或22(23)-烯胺。发现溶剂对区域选择性，如形成N-22和N-16免疫盐的影响是显着的。22(23)-烯胺异构化为相应的20(22)-烯胺，可能是计划化学降解茄碱为类固醇激素的重要中间体，在0.1%乙酸醚或二氯甲烷（氯仿）中进行。
• Products and Mechanisms in the Anodic Oxidation of Solanidine-Type Steroidal Alkaloids
  作者：E. Gunic、I. Tabakovic、K. M. Gasi、D. Miljkovic、I. Juranic

  DOI：10.1021/jo00085a011

  日期：1994.3

  Anodic oxidation of DELTA4-solaniden-3-one, 2,3beta-acetoxysolanidin, 5, and 3beta-acetoxy-5alpha-chlorosolanidin, 6, were performed in CH3CN-CH2Cl2 (1:1)-tetraethylammonium perchlorate electrolyte solution at platinum using controlled potentials. As a result of two-electron oxidation the corresponding N-22 immonium salts (2a, 5a, and 6a) and N-16 immonium salts (2b, 5b, and 6b) were isolated in good yield (75-82%) with a ratio of a/b products of approximately 1.1. The effect of solution conditions on regioselectivity, e.g., formation of 2a and 2b, has been shown to be remarkable. The oxidation of 2 in acetone solution gave 2a in 95 % yield, whereas the oxidation in methylene chloride solution gave 2b in 95% yield. On the basis of the electroanalytical and preparative results as well as molecular orbital calculations with model compounds the mechanism and regioselectivity of the reaction have been deduced.
• Schoepf; Herrmann, Chemische Berichte, 1933, vol. 66, p. 298,302
  作者：Schoepf、Herrmann

  DOI：——

  日期：——
• Clemo et al., Journal of the Chemical Society, 1936, p. 1299
  作者：Clemo et al.

  DOI：——

  日期：——
• Soltys, Chemische Berichte, 1933, vol. 66, p. 762,765
  作者：Soltys

  DOI：——

  日期：——