α-(S,S)-1-(2-piperidyl)-1,2-ethanediol | 117994-55-5

• 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: α-(S,S)-1-(2-piperidyl)-1,2-ethanediol
• 英文别名: (βS,2S)-β-hydroxypiperidin-2-ethanol；(1S)-1-[(2S)-piperidin-2-yl]ethane-1,2-diol
• CAS: 117994-55-5
• 化学式: C₇H₁₅NO₂
• 分子量: 145.202
• InChiKey: XRAQFAXRTAWZCA-NKWVEPMBSA-N

物化性质

• 沸点：
  311.3±22.0 °C(Predicted)
• 密度：
  1.090±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  52.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  α-(S,S)-1-(2-piperidyl)-1,2-ethanediol 在 ruthenium trichloride 、 sodium periodate 、 水 、 potassium carbonate 作用下， 以 四氢呋喃 、 四氯化碳 、 水 、 乙腈 为溶剂， 反应 14.0h， 生成 (D)-N-CBZ-哌啶甲酸
  参考文献：
  名称：

  A short enantioselective synthesis of pipecolic acid

  摘要：

  A simple enantioselective route to pipecolic acid is described. The key step involves the Sharpless asymmetric epoxidation of an N-protected aminoheptenol which spontaneously cyclises to a piperidine derivative on deprotection.

  DOI：

  10.1016/0957-4166(95)00382-7
• 作为产物：
  描述：

  (E)-2-(7-羟基庚-5-烯-1-基)异吲哚-1,3-二酮 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 L-(+)-酒石酸二异丙酯 、 肼 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 生成 α-(S,S)-1-(2-piperidyl)-1,2-ethanediol
  参考文献：
  名称：

  A short enantioselective synthesis of pipecolic acid

  摘要：

  A simple enantioselective route to pipecolic acid is described. The key step involves the Sharpless asymmetric epoxidation of an N-protected aminoheptenol which spontaneously cyclises to a piperidine derivative on deprotection.

  DOI：

  10.1016/0957-4166(95)00382-7

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。
• 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。
• Enantioselective total synthesis of the tricyclic 9-oxabispidine (1R,2S,9S)-11-methyl-13-oxa-7,11-diazatricyclo[7.3.1.02,7]tridecane
  作者：Matthias Breuning、Melanie Steiner

  DOI：10.1016/j.tetasy.2008.08.002

  日期：2008.8

  The enantiomerically pure tricyclic 9-oxabispidine (1R,2S,9S)-11-methyl-13-oxa-7,11-diazatricyclo[7.3.1.0(2.7) ]tridecane, a potential substitute for (+)-sparteine in asymmetric synthesis, was prepared in 7 steps and in 11% overall yield from a chiral epoxy alcohol and (S)-epichlorohydrin. The key intermediate was a bicyclic 9-oxabispidine with an appropriately functionalized, endo-oriented side chain. (C) 2008 Elsevier Ltd. All rights reserved.
• THURKAUF, ANDREW;ZENK, PAUL C.;BALSTER, ROBERT L.;MAY, EVERETTE L.;GEORGE+, J. MED. CHEM., 31,(1988) N 12, C. 2257-2263
  作者：THURKAUF, ANDREW、ZENK, PAUL C.、BALSTER, ROBERT L.、MAY, EVERETTE L.、GEORGE+

  DOI：——

  日期：——
• A short enantioselective synthesis of pipecolic acid
  作者：Concepción Fernández-García、M.Anthony McKervey

  DOI：10.1016/0957-4166(95)00382-7

  日期：1995.12

  A simple enantioselective route to pipecolic acid is described. The key step involves the Sharpless asymmetric epoxidation of an N-protected aminoheptenol which spontaneously cyclises to a piperidine derivative on deprotection.