(S)-N-tosyl-2-hydroxymethylpiperidine | 912806-89-4

• 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: (S)-N-tosyl-2-hydroxymethylpiperidine
• 英文别名: [(2S)-1-(4-Methylbenzene-1-sulfonyl)piperidin-2-yl]methanol；[(2S)-1-(4-methylphenyl)sulfonylpiperidin-2-yl]methanol
• CAS: 912806-89-4
• 化学式: C₁₃H₁₉NO₃S
• 分子量: 269.365
• InChiKey: NYMSIVGSVMZGRH-LBPRGKRZSA-N

物化性质

• 沸点：
  429.2±47.0 °C(Predicted)
• 密度：
  1.226±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-N-tosyl-2-hydroxymethylpiperidine 在 jones reagent 作用下， 以 丙酮 为溶剂， 反应 0.33h， 以89%的产率得到(2S)-1-(4-甲基苯基)磺酰基哌啶-2-羧酸
  参考文献：
  名称：

  Synthesis of Pipecolic Acid and Baikiain

  摘要：

  A straightforward synthesis of pipecolic acid and baikiain was achieved from trans-(2S,4R)-4-hydroxyproline via the key steps of regioselective Baeyer-Villiger reaction and ring-closing metathesis.

  DOI：

  10.3987/com-06-10874
• 作为产物：
  描述：

  (2S)-2-benzyloxymethyl-1-(4-methylphenylsulfonyl)-1,2,3,6-tetrahydropyridine 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 10.0h， 以92%的产率得到(S)-N-tosyl-2-hydroxymethylpiperidine
  参考文献：
  名称：

  Synthesis of Pipecolic Acid and Baikiain

  摘要：

  A straightforward synthesis of pipecolic acid and baikiain was achieved from trans-(2S,4R)-4-hydroxyproline via the key steps of regioselective Baeyer-Villiger reaction and ring-closing metathesis.

  DOI：

  10.3987/com-06-10874

文献信息

• Allylic CH Alkylation of Unactivated α-Olefins: Serial Ligand Catalysis Resumed
  作者：Andrew J. Young、M. Christina White

  DOI：10.1002/anie.201101654

  日期：2011.7.18

  A delicate interplay of several kinetically labile ligands is required for reactions that proceed through serial ligand catalysis mechanisms. An investigation of the disruption of this balance has enabled the development of a method for the intermolecular allylic CH alkylation of unactivated as well as activated α‐olefins (see example, Bn=benzyl).

  通过系列配体催化机制进行的反应需要几个动力学不稳定的配体之间的微妙相互作用。这种平衡的破坏的调查已使的方法的发展的分子间烯丙基Ç  H的未活化的烷基化以及活化的α烯烃（见实施例，BN =苄基）。
• Highly enantioselective hydrogenation of exocyclic double bond of N-tosyloxazolidinones catalyzed by a neutral rhodium complex and its synthetic applications
  作者：Zengming Shen、Xiyan Lu、Aiwen Lei

  DOI：10.1016/j.tet.2006.07.024

  日期：2006.9

  A highly enantioselective synthesis of optically active N-tosyl-4-alkyl-1,3-oxazolidin-2-ones based on the asymmetric hydrogenation of the trisubstituted exocyclic double bond of N-tosyl-4-alkylidene-1,3-oxazolidin-2-ones under the catalysis of neutral [Rh(COD)Cl]2 (COD=1,5-cyclooctadiene) and (S)-(+)-DTBM-SEGPHOS was developed. The utility of this highly enantioselective reaction was exemplified by

  光学活性的对映体选择性高的合成Ñ基于所述三取代的环外双键的不对称氢化甲苯磺酰基-4-烷基-1,3-恶唑烷-2-酮Ñ甲苯磺酰基-4-亚烷基-1,3-恶唑烷在中性[Rh（COD）Cl] 2（COD = 1,5-环辛二烯）和（S）-（+）-DTBM-SEGPHOS的催化下，开发了2-ones。通过合成旋光氨基酸，氨基醇和哌啶衍生物来举例说明这种高对映选择性反应的效用。
• Discovery of Bis-sulfonamides as Novel Inhibitors of Mitochondrial NADH-Quinone Oxidoreductase (Complex I)
  作者：Atsuhito Tsuji、Takahiro Masuya、Norihito Arichi、Shinsuke Inuki、Masatoshi Murai、Hideto Miyoshi、Hiroaki Ohno

  DOI：10.1021/acsmedchemlett.2c00504

  日期：2023.2.9
• Synthesis of Pipecolic Acid and Baikiain
  作者：Meng-Yang Chang、Yung-Hua Kung、Tsun-Cheng Wu

  DOI：10.3987/com-06-10874

  日期：——

  A straightforward synthesis of pipecolic acid and baikiain was achieved from trans-(2S,4R)-4-hydroxyproline via the key steps of regioselective Baeyer-Villiger reaction and ring-closing metathesis.