(3aα,6aβ,9aα)-decahydropyrido<2,1,6-de>quinolizine-2-(1H)-one | 72473-11-1

• 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: (3aα,6aβ,9aα)-decahydropyrido<2,1,6-de>quinolizine-2-(1H)-one
• 英文别名: 13-azatricyclo[7.3.1.0<5,13>]tridecan-3-one
• CAS: 72473-11-1
• 化学式: C₁₂H₁₉NO
• 分子量: 193.289
• InChiKey: GBACHHZJYQACTQ-RTCCRHLQSA-N

物化性质

• 熔点：
  80-81 °C
• 沸点：
  316.4±17.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.12
• 重原子数：
  14.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (3aα,6aβ,9aα)-decahydropyrido<2,1,6-de>quinolizine-2-(1H)-one 在 palladium on activated charcoal 正丁基锂 、 氢气 、 对甲苯磺酸 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 、 xylene 为溶剂， 25.0 ℃ 、303.98 kPa 条件下， 反应 17.25h， 生成 coccinelline
  参考文献：
  名称：

  Stereo- and regioselective total synthesis of the hydropyrido[2,1,6-de]quinolizine ladybug defensive alkaloids

  摘要：

  DOI：

  10.1021/jo00186a029
• 作为产物：
  描述：

  (2R)-2-[(2S,6S)-2-[3-(1,3-dioxolan-2-yl)propyl]-6-(2-methoxyprop-2-enyl)piperidin-1-yl]-2-phenylethanol 在 palladium on activated charcoal 盐酸 、 甲酸 、 camphor-10-sulfonic acid 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 3.5h， 生成 (3aα,6aβ,9aα)-decahydropyrido<2,1,6-de>quinolizine-2-(1H)-one
  参考文献：
  名称：

  A new stereoselective synthesis of ladybug defense alkaloid precoccinelline

  摘要：

  We have accomplished a new stereoselective synthesis of precoccinelline 1 in six steps from the chiral synthon 6 with a overall yield of 31 %. The main feature of this synthesis is the asymmetric synthesis of the trans 2,6-keto-acetal piperidine 14 which assures a stereospecific cyclisation in the construction of key intermediate ketone 4.

  DOI：

  10.1016/s0040-4020(01)81112-1

文献信息

• A new route to trans-2,6-disubstituted piperidine-related alkaloids using a novel C2-symmetric 2,6-diallylpiperidine carboxylic acid methyl ester
  作者：Hiroki Takahata、Yukako Saito、Motohiro Ichinose

  DOI：10.1039/b601489e

  日期：——

  carboxylic acid methyl ester 1 was prepared by the double asymmetric allylboration of glutaldehyde followed by an aminocyclization and carbamation. On the basis of desymmetrization of 1 using iodocarbamation, one allyl group of 1 was protected and monofunctionalizations of the resulting oxazolidinone 11 were performed. The reaction of the N-methoxycarbonyl piperidine 25 employing decarbamation reagent

  通过戊二醛的双不对称烯丙基硼化，然后进行氨基环化和氨基甲酸酯化反应，制备了新型的C2对称的2，6-二烯丙基哌啶羧酸甲酯1。在使用碘代氨基甲酸酯化1的脱对称性的基础上，保护1的一个烯丙基，并对所得的恶唑烷酮11进行单官能化。N-甲氧基羰基哌啶25的反应采用脱氨基化试剂（n-PrSLi或TMSI）作为关键步骤，得到恶唑烷二酮26或17，包括分子内环的形成，在几步中将其转化为（-）-哌啶（2）和（-）-2-表-哌啶（3）。另外，描述了从11开始的（+）-表-二氢吡啶（4），（2R，6R）-反式-肾上腺素A（5）和前古西林碱（6）的方便的合成。
• A Novel <i>C</i>₂-Symmetric 2,6-Diallylpiperidine Carboxylic Acid Methyl Ester as a Promising Chiral Building Block for Piperidine-Related Alkaloids
  作者：Hiroki Takahata、Hidekazu Ouchi、Motohiro Ichinose、Hideo Nemoto

  DOI：10.1021/ol0265620

  日期：2002.10.1

  1-carboxylic acid methyl ester (5) was examined via the double asymmetric allylboration of glutaraldehyde followed by aminocyclization and carbamation as a promising chiral building block for piperidine-related alkaloids, which were synthesized by the desymmetrization of 5 using intramolecular iodocarbamation as a key step. [reaction: see text]

  C（2）对称的2,6-二烯丙基哌啶1-羧酸甲酯（5）通过戊二醛的双不对称烯丙基硼化，然后进行氨基环化和氨基甲酸酯化反应，作为哌啶相关生物碱的有前途的手性构建基，通过使用分子内碘代氨基甲酸酯化作为关键步骤的5脱对称化。[反应：看文字]
• Synthesis of Derivatives of 1, 2, 6-Trisubstttuted-4-Piperidones
  作者：Michel Langlois、Donglaï Yang、Jean-Louis Soulier、Claudie Florac

  DOI：10.1080/00397919209409262

  日期：1992.11

  Robinson-Schopf cyclisation was used to prepare several 1,2,6-trisubstituted-4-piperidones. 1,2,6-trimethyl-4-piperidone, tricyclic ketones 2 and 3 derivatives of coccinelline. In the case of 1,2,6-trimethyl-4-piperidone, a mixture of the trans and cis compounds 4 and 1 was obtained. The pure cis compound was prepared by another route.
• Stereo- and regioselective total synthesis of the hydropyrido[2,1,6-de]quinolizine ladybug defensive alkaloids
  作者：Richard H. Mueller、Mark E. Thompson、Robert M. DiPardo

  DOI：10.1021/jo00186a029

  日期：1984.6
• A new stereoselective synthesis of ladybug defense alkaloid precoccinelline
  作者：Chongwei Yue、Jean-François Nicolay、Jacques Royer、Henri-Philippe Husson

  DOI：10.1016/s0040-4020(01)81112-1

  日期：1994.3

  We have accomplished a new stereoselective synthesis of precoccinelline 1 in six steps from the chiral synthon 6 with a overall yield of 31 %. The main feature of this synthesis is the asymmetric synthesis of the trans 2,6-keto-acetal piperidine 14 which assures a stereospecific cyclisation in the construction of key intermediate ketone 4.