N-Cbz-9-氮杂双环[3.3.1]壬烷-3-酮 | 146747-65-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-Cbz-9-氮杂双环[3.3.1]壬烷-3-酮
• 中文别名: N-CBZ-9-氮杂双环[3.3.1]壬烷-3-酮
• 英文名称: benzyl 3-oxo-9-azabicyclo<3.3.1>nonanane-9-carboxylate
• 英文别名: Benzyl 3-oxo-9-azabicyclo[3.3.1]nonane-9-carboxylate
• CAS: 146747-65-1
• 化学式: C₁₆H₁₉NO₃
• 分子量: 273.332
• InChiKey: PECCPMURUGQWAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  N-Cbz-9-氮杂双环[3.3.1]壬烷-3-酮 在 diethylzinc 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成
  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

文献信息

• Tandem Beckmann and Huisgen–White rearrangement as an alternative to the Baeyer–Villiger oxidation of the bicyclo[3.3.1]nonane system: first asymmetric synthesis of (–)-dihydropalustramic acid. X-Ray molecular structure of 2β-ethyl-9-phenylsulfonyl-9-azabicyclo[3.3.1]nonan-3-one
  作者：Osamu Muraoka、Bao-Zhong Zheng、Kazuhito Okumura、Genzoh Tanabe、Takefumi Momose、Conrad Hans Eugster

  DOI：10.1039/p19960001567

  日期：——

  The transformation of the ‘fork head ketone’ 3b into the corresponding bicyclic lactone 13 via the Beckmann followed by the Huisgen–White rearrangement is described. Application of the method to a homochiral 2-etyl-substituted bicyclic ketone (+)-3dα gave efficiently (–)-dihydropalustramic acid (–)-2a, a degradation product from the alkaloid palustrine 1, in good optical yield.

  描述了通过贝克曼将“叉头酮” 3b转变为相应的双环内酯13 ，然后进行了惠斯根-怀特重排。该方法在同手性2-乙基取代的双环酮（+）-3dα上的应用可有效地产生（-）-二氢palustramic酸（-）-2a，这是生物碱palustrine 1的降解产物，具有良好的光学收率。
• 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.
• Bicyclo[3.3.1]nonanes as Synthetic Intermediates. XXIII.¹A Breakthrough by Lanthanoid Mediation in Nucleophilic Addition of Carbanions to the Inert “Fork Head” Carbonyl in Bicyclo[3.3.1]nonan-3-ones
  作者：Takefumi Momose、Shinobu Takizawa、Masayuki Kirihara

  DOI：10.1080/00397919708005631

  日期：1997.10

  Owing to the ''backside steric hindrance'', the 'fork head ketone' (C-3 ketone) in bicyclo[3.3.1]nonan-3-ones is quite inactive against a nucleophilic attack of several kinds of organometallic reagents. Organocerium reagents and samarium iodide / organohalides turned out to react with the fork head ketone to afford the corresponding adducts efficiently.
• Efficient synthesis of an enantiomeric pair pinpinidine: An illustration of organochemical carving on the rigid bridged system as the stereochemical tactics
  作者：Takefumi Momose、Takashi Nishio、Masayuki Kirihara

  DOI：10.1016/0040-4039(96)00990-2

  日期：1996.7

  Asymmetric synthesis of (−)-pinidine and its enantiomer was accomplished by starting from norgranatar one via the asymmetric enolization, stereoselective cyclopropanation, and oxidative ring cleavage of the resulting cyclopropanol system with a hypervalent iodoid as key steps.

  （-）-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。