(2S)-1-(4-甲基苯基)磺酰基哌啶-2-羧酸 | 56099-73-1

• 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: (2S)-1-(4-甲基苯基)磺酰基哌啶-2-羧酸
• 英文名称: (2S)-1-(4-methylphenylsulfonyl)piperidine-2-carboxylic acid
• 英文别名: (S)-N-tosylpipecolic acid；N-tosyl-L-pipecolic acid；N-tosylpipecolic acid；(2S)-1-(4-methylphenyl)sulfonylpiperidine-2-carboxylic acid
• CAS: 56099-73-1
• 化学式: C₁₃H₁₇NO₄S
• mdl: MFCD23211241
• 分子量: 283.348
• InChiKey: GCWLCINIEOOJGU-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S)-1-(4-甲基苯基)磺酰基哌啶-2-羧酸 在 sodium amalgam 、 sodium phosphate 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以80%的产率得到L-哌啶-2-甲酸
  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：

  (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

文献信息

• 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。
• Complementary routes to both enantiomers of pipecolic acid and 4,5-dihydroxypipecolic acid derivatives
  作者：Shital K. Chattopadhyay、Titas Biswas、Tanmoy Biswas

  DOI：10.1016/j.tetlet.2007.12.097

  日期：2008.2

  Complementary new routes to both enantiomers of N-protected pipecolic acid and the corresponding 4,5-dihydroxylated derivatives are developed, which involve stereo-divergent allylation of a chiral N-allylimine and ring-closing metathesis as key steps.

  已开发出同时获得N-保护的胡椒酸对映异构体和相应的4,5-二羟基化衍生物的互补新途径，其中涉及手性N-烯丙胺的立体发散烯丙基化和闭环易位作为关键步骤。
• 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.