(3aR,5aS,7S,8bR)-8-Butyl-7-methyl-3,3a,4,5,5a,6,7,8b-octahydro-1H-cyclopenta[de]quinazolin-2-ylideneamine; compound with nitric acid | 202646-37-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并嘧啶类
• 英文名称: (3aR,5aS,7S,8bR)-8-Butyl-7-methyl-3,3a,4,5,5a,6,7,8b-octahydro-1H-cyclopenta[de]quinazolin-2-ylideneamine; compound with nitric acid
• 英文别名: (1S,4R,10S,12R)-9-butyl-10-methyl-5,7-diazatricyclo[6.3.1.04,12]dodeca-5,8-dien-6-amine;nitric acid
• CAS: 202646-37-5
• 化学式: C₁₅H₂₅N₃*HNO₃
• 分子量: 310.396
• InChiKey: UVZNDTFFVRXAFI-QOYNJTQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.65
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  111.28
• 氢给体数：
  4.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (3S,5S)-2-[(E)-but-2-enyl]-5-[2-(1,3-dioxolan-2-yl)ethyl]-3-methylcyclohexan-1-one 在 palladium on activated charcoal 盐酸 、 氢气 、 硝酸 作用下， 以 四氢呋喃 为溶剂， 反应 27.0h， 生成 (3aR,5aS,7S,8bR)-8-Butyl-7-methyl-3,3a,4,5,5a,6,7,8b-octahydro-1H-cyclopenta[de]quinazolin-2-ylideneamine; compound with nitric acid
  参考文献：
  名称：

  （+）-木瓜蛋白酶的全合成

  摘要：

  描述了（+）-木瓜蛋白酶的首次合成。

  DOI：

  10.1016/s0040-4039(00)97726-8

文献信息

• Chiral [η6-Arene-Cr(CO)3] Complexes as Synthetic Building Blocks: A Short Enantioselective Total Synthesis of (+)-Ptilocaulin
  作者：Kurt Schellhaas、Hans-Günther Schmalz、Jan W. Bats

  DOI：10.1002/(sici)1521-3765(199801)4:1<57::aid-chem57>3.0.co;2-h

  日期：1998.1

  An enantioselective total synthesis of the marine natural product (+)-ptilocaulin is described. The synthesis starts from [anisole-Cr(CO)(3)], which is converted to [2-trimethylsilylanisole - Cr(Co)(3)] (greater than or equal to 99 % ee) by enantioselective deprotonation/silyLation and recrystallization. After attachment of a 2-butenyl side-chain, nucleophile addition (2-lithio-1,3-dithiane) followed by treatment with chloratrimethylsilane and hydrolysis leads to (5S,6S)-6-((E)-but-2-enyl)-5-[1,3]-dithian-2-yl-2-trimethylsilylcyclohex-2-enone with complete chirality transfer. This compound, which was characterized by X-ray crystallography, is transformed into (5 xi,6S,7aS)-5-butpl-6-methyl-1,2,5,6,7,7a-hexahydro-inden-4-one, a ptilocaulin precursor known from the literature, by a 4-step sequence consisting of diastereoselective 1,4-addition, ultrasound-assisted desulfurization/hydrogenation (Raney Ni) and aldol cyclization. The target molecule was prepared in both racemic and optically active form. The X-ray crystal structure of rac-ptilocaulin nitrate shows flat ribbons of homochiral units (parallel double chains) connected by an interesting pattern of hydrogen bonds between the guanidinium and the nitrate ions. A different mode of hydrogen bonding resulting in the formation of helical monochains was found in the solid-state structure of (+)-ptilocaulin co-crystallized with about 29 % of its C-3a epimer.
• ASAOKA, MORIO;SAKURAI, MASAHITO;TAKEI, HISASHI, TETRAHEDRON LETT., 31,(1990) N3, C. 4759-4760
  作者：ASAOKA, MORIO、SAKURAI, MASAHITO、TAKEI, HISASHI

  DOI：——

  日期：——