1-(hydroxymethyl)-2-hydroxy-1-(5,12-dimethyl-9-methylene-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindol-8-yl)propane | 126790-63-4

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: 1-(hydroxymethyl)-2-hydroxy-1-(5,12-dimethyl-9-methylene-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindol-8-yl)propane
• 英文别名: 2-[(1S,12S,14S)-3,16-dimethyl-13-methylidene-3,16-diazatetracyclo[10.3.1.02,10.04,9]hexadeca-2(10),4,6,8-tetraen-14-yl]butane-1,3-diol
• CAS: 126790-63-4
• 化学式: C₂₁H₂₈N₂O₂
• 分子量: 340.466
• InChiKey: WAUWHQHNCYYEPB-WMYJNMORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.64
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  48.63
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-(hydroxymethyl)-2-hydroxy-1-(5,12-dimethyl-9-methylene-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindol-8-yl)propane 在 吡啶 、 sodium hydroxide 、 重铬酸吡啶 、 9-borabicyclo[3.3.1]nonane dimer 、 四丁基氟化铵 、 双氧水 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 生成 (+)-macroline
  参考文献：
  名称：

  合成大分子/ sarpagine生物碱的通用方法。（+）-大麦碱的总合成

  摘要：

  由四环酮5合成了（+）-甲基1和更稳定的当量2。合成中的关键步骤涉及立体选择性Claisen重排，然后对所得烯烃14进行硼氢化氧化，以在C-15和C-16处设置正确的立体化学。

  DOI：

  10.1016/0040-4039(93)88069-u
• 作为产物：
  描述：

  (6S,10S)-(-)-5,12-dimethyl-9-<<(3-oxo-1-(E)-butenyl)oxy>methyl>-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctindole 在 sodium tetrahydroborate 作用下， 以 乙醚 、 苯 为溶剂， 生成 1-(hydroxymethyl)-2-hydroxy-1-(5,12-dimethyl-9-methylene-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindol-8-yl)propane
  参考文献：
  名称：

  General approach to the synthesis of macroline-related alkaloids. Stereospecific total synthesis of (-)-alstonerine

  摘要：

  DOI：

  10.1021/ja00166a084

文献信息

• General approach for the synthesis of macroline/sarpagine related indole alkaloids via the asymmetric Pictet-Spengler reaction: The enantiospecific synthesis of (−)-anhydromacrosalhine-methine
  作者：Tong Gan、James M. Cook

  DOI：10.1016/0040-4039(96)01009-x

  日期：1996.7

  An enantiospecific total synthesis of (−)-anhydromacrosalhine-methine 3a has been accomplished from D-(+)-tryptophan via the asymmetric Pictet-Spengler reaction. A partial synthesis of 3a from the natural product (+)-ajmaline has also been completed.

  通过不对称的Pictet-Spengler反应，由D-（+）-色氨酸完成了对映体的（-）-脱水甲基甲硫氨酸-次甲基3a的全合成。还已经完成了从天然产物（+）-ajmaline的3a部分合成。
• Enantiospecific Synthesis of (-)-Alstonerine and (+)-Macroline as Well as a Partial Synthesis of (+)-Villalstonine
  作者：Yingzhi Bi、Lin-Hua Zhang、Linda K. Hamaker、James M. Cook

  DOI：10.1021/ja00099a021

  日期：1994.10

  The enantiospecific synthesis of (-)-alstonerine (5) and (+)-macroline (8), as well as a partial synthesis of the Alstonia bisindole alkaloid villalstonine (2) has been completed. In addition, a more stable macroline equivalent 9 was prepared. The stereochemistry at C(15) and C(16) in 5 and 8 has been successfully installed by a stereoselective Claisen rearrangement followed by stereospecific hydroboration-oxidation of the exocyclic methylene function at C-16. The E ring in alstonerine 5 was constructed by a regioselective cyclization followed by a novel Swern oxidation under modified conditions [(COCl)(2)/DMSO/CH2Cl2, -78 degrees C to -10 degrees C/1.5 h; Et(3)N], whereas the C(20)-C(21) enone system in macroline (8) was generated via a convenient one pot process from the beta-diol 45. Condensation of either synthetic (+)-macroline (8) or the macroline equivalent 9 with natural pleiocarpamine 7 in 0.2 N HCl furnished the antiamoebic, antimalarial bisindole alkaloid villalstonine 2. This constitutes the first partial synthesis of any of the Alstonia bisindoles from a synthetically derived indole moiety.
• ZHANG, L. H.;COOK, J. M., J. AMER. CHEM. SOC., 112,(1990) N0, C. 4088-4090
  作者：ZHANG, L. H.、COOK, J. M.

  DOI：——

  日期：——