petrosin A

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹嗪类
• 英文名称: petrosin A
• 英文别名: (1S,7S,9S,15R,21R,23R,29S,30R)-9,23-dimethyl-11,25-diazapentacyclo[19.7.1.17,11.025,29.015,30]triacontane-8,22-dione
• 化学式: C₃₀H₅₀N₂O₂
• 分子量: 470.739
• InChiKey: OCNVVYBTRKWBCO-WBSIONKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  34
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  petrosin A 在 sodium cyanoborohydride 作用下， 以 乙醇 为溶剂， 生成
  参考文献：
  名称：

  Aragupetrosine一个，一个新的血管舒张的大环喹从冲绳海绵生物碱SP

  摘要：

  从冲绳海洋海绵菌种中分离出一种新的血管舒张性喹诺唑烷生物碱，名为aragupetrosine A（7）。阐明了金刚烷胺A的绝对立体结构为7，其是石油蛋白（1）和金刚烷胺F（12）的杂种。

  DOI：

  10.1016/s0040-4039(00)99345-6
• 作为产物：
  描述：

  在 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 Petrosin 、 petrosin A 、 (+/-)-petrosin B
  参考文献：
  名称：

  Total Synthesis of Petrosin

  摘要：

  DOI：

  10.1021/ja00098a073

文献信息

• Total Synthesis of Petrosin, Petrosin A, and Petrosin B
  作者：Robert W. Scott、James Epperson、Clayton H. Heathcock

  DOI：10.1021/jo9801768

  日期：1998.7.1

  The petrosins are a family of marine alkaloids that includes the chiral, racemic isomer petrosin (1), the meso isomer petrosin A (2), and the chiral, scalemic isomer petrosin B (3). Monte Carlo molecular mechanics calculations indicated that petrosin (1) is the most stable isomer of the group, suggesting that it might be synthesized by a route that utilizes thermodynamic control for establishing the relative configurations of the eight stereocenters. The model synthesis summarized in Scheme 1 showed that intramolecular Mannich condensation is a viable route to the quinolizidone subunit of the petrosins and that this synthesis gives isomer 5, having the relative configuration found in petrosin and petrosin A, as the kinetic product. Equilibration studies with this isomer afforded an approximate equimolar mixture of 5 and diastereomer 6, having the relative configuration found in one of the two quinolizidone milts of petrosin B. On the basis of this model study, a "stereo-uncontrolled" synthesis of petrosin was carried out, as summarized in Schemes 3-5. The key step of this synthesis is a "double-barrelled" intramolecular Mannich condensation of a diamino keto dialdehyde. This transformation provides crystalline petrosin in 23% yield, along with about 37% of a mixture of petrosin diastereomers. Although simple acid- and Lewis acid-mediated equilibrations of this mixture of diastereomers were not successful, the derived mixture of bis-butylimines undergoes equilibration upon treatment with protic acid to give a mixture that is greatly enriched in petrosin, relative to the other isomers. Crystallization of this equilibration mixture provided another 10% of petrosin, bringing the overall yield of petrosin to 33%. In the course of the equilibration studies, pure samples of petrosin A (2), petrosin B (3), and petrosin B' (7) were isolated and characterized.
• Total Synthesis of Petrosin
  作者：Robert W. Scott、James R. Epperson、Clayton H. Heathcock

  DOI：10.1021/ja00098a073

  日期：1994.9
• Aragupetrosine a, a new vasodilative macrocyclic quinolizidine alkaloid from an Okinawan marine sponge sp
  作者：Motomasa Kobayashi、Kazuyoshi Kawazoe、Isao Kitagawa

  DOI：10.1016/s0040-4039(00)99345-6

  日期：1989.1

  A new vasodilative quinolizidine alkaloid named aragupetrosine A (7) was isolated from an Okinawan marine sponge sp. The absolute stereostructure of aragupetrosine A was elucidated to be 7 which was a hybrid of petrosin (1) and araguspongine F (12).

  从冲绳海洋海绵菌种中分离出一种新的血管舒张性喹诺唑烷生物碱，名为aragupetrosine A（7）。阐明了金刚烷胺A的绝对立体结构为7，其是石油蛋白（1）和金刚烷胺F（12）的杂种。