tert-butyl (2S)-2-[(1S)-1,2-dihydroxyethyl]piperidine-1-carboxylate | 417726-34-2

• 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: tert-butyl (2S)-2-[(1S)-1,2-dihydroxyethyl]piperidine-1-carboxylate
• CAS: 417726-34-2
• 化学式: C₁₂H₂₃NO₄
• 分子量: 245.319
• InChiKey: JBQYOMWZWWNBBG-VHSXEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  70
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S)-2-[(1S)-1,2-dihydroxyethyl]piperidine-1-carboxylate 在 potassium permanganate 、 sodium periodate 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以98%的产率得到N-Boc-L-哌啶-2-羧酸
  参考文献：
  名称：

  Straightforward entry to the pipecolic acid nucleus. Enantioselective synthesis of baikiain

  摘要：

  New enantioselective syntheses of N-protected baikiain and pipecolic acid have been developed. The starting material is 2,3-epoxy-5-hexen-1-ol (4) readily available in high ee by Sharpless epoxidation. The regio- and stereoselective epoxide ring-opening by allylamine afforded a doubly unsaturated amine that was converted into a carbamate (Boc) and submitted to ring-closing metathesis. The resulting cyclic amino diol 6 is a key intermediate that was converted into N-Boc-baikiain and several pipecolic acid derivatives. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02271-7
• 作为产物：
  描述：

  ((2R,3R)-3-allyloxiran-2-yl)methanol 在 palladium on activated charcoal 、 Grubbs catalyst first generation 氢气 、 lithium perchlorate 、 碳酸氢钠 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 、 乙腈 为溶剂， 生成 tert-butyl (2S)-2-[(1S)-1,2-dihydroxyethyl]piperidine-1-carboxylate
  参考文献：
  名称：

  Straightforward entry to the pipecolic acid nucleus. Enantioselective synthesis of baikiain

  摘要：

  New enantioselective syntheses of N-protected baikiain and pipecolic acid have been developed. The starting material is 2,3-epoxy-5-hexen-1-ol (4) readily available in high ee by Sharpless epoxidation. The regio- and stereoselective epoxide ring-opening by allylamine afforded a doubly unsaturated amine that was converted into a carbamate (Boc) and submitted to ring-closing metathesis. The resulting cyclic amino diol 6 is a key intermediate that was converted into N-Boc-baikiain and several pipecolic acid derivatives. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02271-7

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。