(2S,2'S)-N-Cbz-2-(2'-oxiranyl)piperidine | 1092706-37-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,2'S)-N-Cbz-2-(2'-oxiranyl)piperidine
• 英文别名: benzyl (2S)-2-[(2S)-oxiran-2-yl]piperidine-1-carboxylate
• CAS: 1092706-37-0
• 化学式: C₁₅H₁₉NO₃
• 分子量: 261.321
• InChiKey: BHUDXKYBEMSMFQ-UONOGXRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  42.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  lithium dimethylcuprate 、 (2S,2'S)-N-Cbz-2-(2'-oxiranyl)piperidine 以 乙醚 为溶剂， 以78%的产率得到N-Cbz-(+)-α-conhydrine
  参考文献：
  名称：

  A highly stereocontrolled route to 2-(2′-oxiranyl)piperidines and pyrrolidines: enantioselective synthesis of (+)-α-conhydrine

  摘要：

  The first enantio- and diastereoselective approach to both 2-(2'-oxiranyl)piperidines and to 2-(2'-oxiranyl)pyrrolidines is reported. The method relies on the Sharpless asymmetric epoxidation of allyl alcohols as the sole source of chirality, and involves as the key step the base-mediated cyclization of (alpha-aminoalkyl)oxiranes functionalized at the is an element of (or delta) position. The asymmetric synthesis of (+)-alpha-conhydrine illustrates the applicability of this strategy to the preparation of biologically active 2-(1-hydroxyalkyl)piperidine alkaloids. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.09.095
• 作为产物：
  描述：

  [(5S)-5-[(2S)-oxiran-2-yl]-5-(phenylmethoxycarbonylamino)pentyl] methanesulfonate 在 sodium hexamethyldisilazane 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (2S,2'S)-N-Cbz-2-(2'-oxiranyl)piperidine
  参考文献：
  名称：

  A highly stereocontrolled route to 2-(2′-oxiranyl)piperidines and pyrrolidines: enantioselective synthesis of (+)-α-conhydrine

  摘要：

  The first enantio- and diastereoselective approach to both 2-(2'-oxiranyl)piperidines and to 2-(2'-oxiranyl)pyrrolidines is reported. The method relies on the Sharpless asymmetric epoxidation of allyl alcohols as the sole source of chirality, and involves as the key step the base-mediated cyclization of (alpha-aminoalkyl)oxiranes functionalized at the is an element of (or delta) position. The asymmetric synthesis of (+)-alpha-conhydrine illustrates the applicability of this strategy to the preparation of biologically active 2-(1-hydroxyalkyl)piperidine alkaloids. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.09.095

文献信息

• A concise diastereoselective approach to (+)-dexoxadrol, (−)-epi-dexoxadrol, (−)-conhydrine and (+)-lentiginosine from (−)-pipecolinic acid
  作者：Chinmay Bhat、Santosh G. Tilve

  DOI：10.1016/j.tet.2013.10.082

  日期：2013.12

  A new diastereoselective pathway for the total synthesis of (+)-dexoxadrol, first asymmetric synthesis of (−)-epi-dexoxadrol and formal synthesis of conhydrine and (+)-lentiginosine is presented using commercially available (−)-pipecolinic acid. The key reactions utilized are Sharpless asymmetric dihydroxylation and Wittig reaction. The paper further describes the study of effect of protecting groups

  使用市售的（-）-哌啉酸，提出了一种新的非对映选择性途径，用于全合成（+）-右氧杂醇，（-）-表-右氧杂戊醇的首次不对称合成以及Conhydroine和（+）-lentiginosine的形式合成。使用的关键反应是Sharpless不对称二羟基化反应和Wittig反应。该论文进一步描述了保护基对哌啶环系统中末端烯烃的二羟基化作用的研究。
• Synthetic Studies of Alkaloids Containing Pyrrolidine and Piperidine Structural Motifs
  作者：Chinmay Bhat

  DOI：10.1002/open.201402128

  日期：2015.4

  Avenues to asymmetric alkaloids! Various 2‐substituted pyrrolidine and piperidine chiral bioactive natural products were synthesized using a ‘chiral pool’ method. l‐proline and l‐pipecolinic acids with one chiral center served as the best precursors for the synthesis of these alkaloids. Overall, 14 total synthetic and 11 formal synthetic approaches were developed.

  不对称生物碱的大道！使用“手性库”方法合成了各种2-取代的吡咯烷和哌啶手性生物活性天然产物。带有一个手性中心的l-脯氨酸和l- pipecolinic酸是合成这些生物碱的最佳前体。总的来说，共开发了14种综合合成方法和11种正式合成方法。
• A highly stereocontrolled route to 2-(2′-oxiranyl)piperidines and pyrrolidines: enantioselective synthesis of (+)-α-conhydrine
  作者：Dídac Rodríguez、Anna Picó、Albert Moyano

  DOI：10.1016/j.tetlet.2008.09.095

  日期：2008.11

  The first enantio- and diastereoselective approach to both 2-(2'-oxiranyl)piperidines and to 2-(2'-oxiranyl)pyrrolidines is reported. The method relies on the Sharpless asymmetric epoxidation of allyl alcohols as the sole source of chirality, and involves as the key step the base-mediated cyclization of (alpha-aminoalkyl)oxiranes functionalized at the is an element of (or delta) position. The asymmetric synthesis of (+)-alpha-conhydrine illustrates the applicability of this strategy to the preparation of biologically active 2-(1-hydroxyalkyl)piperidine alkaloids. (c) 2008 Elsevier Ltd. All rights reserved.