<(5aS,9aR)-11,14b-Dihydroxy-(5ar,6ac,14bc)-1,3,5a,6,6a,8,9,14b-octahydro-5,7-methano-oxepino<3,4-a>pyrrolo<2,3-d>carbazol-1c-yl> essigsaeure-14b-lactone | 169898-93-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: <(5aS,9aR)-11,14b-Dihydroxy-(5ar,6ac,14bc)-1,3,5a,6,6a,8,9,14b-octahydro-5,7-methano-oxepino<3,4-a>pyrrolo<2,3-d>carbazol-1c-yl> essigsaeure-14b-lactone
• 英文别名: 2,13-dihydroxy-8,9-didehydro-9,10-seco-12βH-strychnidin-10-oic acid-13-lactone；2,13-Dihydroxy-8,9-didehydro-9,10-seco-12βH-strychnidin-10-saeure-13-lacton；2,13-Dihydroxy-8,9-didehydro-9,10-seco-strychnidin-10-saeure-13-lacton
• CAS: 169898-93-5
• 化学式: C₂₁H₂₀N₂O₄
• 分子量: 364.401
• InChiKey: ROPQXKSOKXCCOE-JMUDTHNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.83
• 重原子数：
  27.0
• 可旋转键数：
  0.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  71.36
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  <(5aS,9aR)-11,14b-Dihydroxy-(5ar,6ac,14bc)-1,3,5a,6,6a,8,9,14b-octahydro-5,7-methano-oxepino<3,4-a>pyrrolo<2,3-d>carbazol-1c-yl> essigsaeure-14b-lactone 在 盐酸 、 铂 作用下， 生成 2,13-dihydroxy-7,8-didehydro-7,16;9,10-diseco-12βH-strychnidin-10-oic acid-13-lactone
  参考文献：
  名称：

  Teuber; Fahrbach, Chemische Berichte, 1958, vol. 91, p. 713,733, 735, 738, 739

  摘要：

  DOI：
• 作为产物：
  描述：

  Strychninic acid 在 potassium nitrososulfonate 作用下， 生成 <(5aS,9aR)-11,14b-Dihydroxy-(5ar,6ac,14bc)-1,3,5a,6,6a,8,9,14b-octahydro-5,7-methano-oxepino<3,4-a>pyrrolo<2,3-d>carbazol-1c-yl> essigsaeure-14b-lactone
  参考文献：
  名称：

  Teuber; Fahrbach, Chemische Berichte, 1958, vol. 91, p. 713,733, 735, 738, 739

  摘要：

  DOI：

文献信息

• Ein �bergang aus der Strychnin- in die Heteroyohimban-Reihe der Indolalkaloide durch oxidative Umlagerung von Isostrychnins�ure
  作者：Hans-Joachim Teuber、Olav Lahnstein

  DOI：10.1002/prac.19953370199

  日期：——

  By peroxyacid oxidation of isostrychnic acid there are formed, together with the amine oxide of base 2, three isomeric lactone bases, C21H20N2O4, which are formulated as 3-5. Reduction of the isatogen 5 leads to ring opening on both sides of the indole nitrogen (6, 7), and hydrochloric acid introduces a chloro atom in p-position to the nitrogen (9). - Both tautomeric forms of 2 can be fixated by reduction to 8 and 10, respectively. - The lactone ring of 2 is hydrolyzed by hot dilute hydrochloric acid, followed by rearrangement to the heteroyohimbane type indoloquinolizidine 12. Compound 12, featuring as keto-enol and amino acid, can be reduced and cyclised with mineral acid to the lactone 14 (two diasteroisomers) serving for X-ray structural analysis. Treatment of 12 with acetic anhydride-afforded the lactone 20 by rearrangement of the double bonds. Further hydrogenation products of 12 are described (15, 16, 18) and their spectra, including mass and CD spectra, are discussed. Biochemical implications are referred, too.