methyl 3-oxo-9-azabicyclo[3.3.1]nonane-9-carboxylate | 93460-50-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: methyl 3-oxo-9-azabicyclo[3.3.1]nonane-9-carboxylate
• CAS: 93460-50-5
• 化学式: C₁₀H₁₅NO₃
• 分子量: 197.234
• InChiKey: HATTWYXLTGDBKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 3-oxo-9-azabicyclo[3.3.1]nonane-9-carboxylate 在 diethylzinc 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 methyl (1R,2R,4S,6S)-3-methyl-4-(trimethylsilyloxy)-10-azatricyclo<4.3.1.0^2,4>decane-10-carboxylate
  参考文献：
  名称：

  对映体对pinpinidine的高效合成：刚性桥接系统上的有机化学雕刻插图，作为立体化学策略

  摘要：

  （-）-吡啶和其对映异构体的不对称合成是通过从炔诺酮开始，通过不对称烯醇化，立体选择性环丙烷化和所得环丙醇系统的氧化环裂解（以高价碘）为关键步骤来完成的。

  DOI：

  10.1016/0040-4039(96)00990-2
• 作为产物：
  描述：

  N-Boc-9-氮杂双环[3.3.1]壬烷-3-酮 在 盐酸 、 水 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 methyl 3-oxo-9-azabicyclo[3.3.1]nonane-9-carboxylate
  参考文献：
  名称：

  Scaffold hopping approach towards various AFQ-056 analogs as potent metabotropic glutamate receptor 5 negative allosteric modulators

  摘要：

  The metabotropic glutamate receptor subtype 5 has evolved into a promising target for the treatment of various diseases of the central nervous system, such as Fragile X and L-DOPA induced dyskinesia. One of the most advanced clinical compound is Novartis' AFQ-056 (Mavoglurant), which served us as a template for a scaffold hopping approach, generating a structurally diverse set of potent analogs. Both the limited aqueous solubility and the relatively poor metabolic stability of AFQ-056 were improved with hexahydrocyclopenta[c]pyrrole derivative 54a, which proved to be a valuable candidate for further development. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.09.059

文献信息

• Asymmetric Cleavage of 9-Azabicyclo[3.3.1]nonan-3-one into<i>cis</i>-2,6-Disubstituted Piperidine. A Facile Approach to a Chiral Building Block for Alkaloid Synthesis
  作者：Takefumi Momose、Naoki Toyooka、Yoshiro Hirai

  DOI：10.1246/cl.1990.1319

  日期：1990.8

  An asymmetric cleavage of the ‘fork head’ ketone of 9-azabicyclo[3.3.1]nonan-3-one gave a cis-2,6-disubstituted piperidine derivative in 93% ee, which was transformed to the cis-2,6-bis(hydroxymethyl)piperidine derivative, a versatile chiral building block.

  9-氮杂双环 [3.3.1]nonan-3-one 的“叉头”酮的不对称裂解得到 93% ee 的 cis-2,6-二取代哌啶衍生物，其转化为 cis-2,6 -双（羟甲基）哌啶衍生物，一种通用的手性结构单元。
• Hypervalent λn-iodane-mediated fragmentation of tertiary cyclopropanol systems
  作者：Masayuki Kirihara、Satoshi Yokoyama、Hiroko Kakuda、Takefumi Momose

  DOI：10.1016/s0040-4020(98)00862-x

  日期：1998.11

  The oxidation of tertiary cyclopropyl silyl ethers with hypervalent lambda(n)-iodanes caused fragmentation which produced alkenoic acids or esters. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Hypervalent λn-iodane-mediated fragmentation of tertiary cyclopropanol systems II: Application to asymmetric syntheses of piperidine and indolizidine alkaloids
  作者：Masayuki Kirihara、Takashi Nishio、Satoshi Yokoyama、Hiroko Kakuda、Takefumi Momose

  DOI：10.1016/s0040-4020(99)00073-3

  日期：1999.3

  The asymmetric synthesis of (-)-pinidine and its enantiomer was accomplished by starting from norgranatanone via the asymmetric enolization, stereoselective cyclopropanation, and oxidative ring cleavage of the resulting cyclopropanol system with a hypervalent lambda(n)-iodane as key steps. Formal asymmetric synthesis of (+)-indolizidine 223AB was also performed via the asymmetric enolization and oxidative ring cleavage of the resulting cyclopropanol system as key steps. (C) 1999 Elsevier Science Ltd. All rights reserved.
• MOMOSE, TAKEFUMI;TOYOOKA, NAOKI;HIRAI, YOSHIRO, CHEM. LETT.,(1990) N, C. 1319-1322
  作者：MOMOSE, TAKEFUMI、TOYOOKA, NAOKI、HIRAI, YOSHIRO

  DOI：——

  日期：——
• MOMOSE, TAKEFUMI;MURAOKA, OSAMU;MUSADA, KIKUO, CHEM. AND PHARM. BULL., 1984, 32, N 9, 3730-3733
  作者：MOMOSE, TAKEFUMI、MURAOKA, OSAMU、MUSADA, KIKUO

  DOI：——

  日期：——