1-(4-methylbenzenesulfonyl)pipecolic acid | 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
• 英文名称: 1-(4-methylbenzenesulfonyl)pipecolic acid
• 英文别名: (+/-)-(4-toluenesulfonyl)-piperidine-2-carboxylic acid；(+/-)-N-tosylpiperidine-2-carboxylic acid；1-(Toluene-4-sulfonyl)-piperidine-2-carboxylic acid；1-(4-methylphenyl)sulfonylpiperidine-2-carboxylic acid
• CAS: 56099-73-1；144630-15-9
• 化学式: C₁₃H₁₇NO₄S
• mdl: MFCD00726296
• 分子量: 283.348
• InChiKey: GCWLCINIEOOJGU-UHFFFAOYSA-N

物化性质

• 熔点：
  101-102 °C
• 沸点：
  477.6±55.0 °C(Predicted)
• 密度：
  1.328±0.06 g/cm3(Predicted)

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

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  1-(4-methylbenzenesulfonyl)pipecolic acid 在 萘 、 sodium 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 以89%的产率得到六氢吡啶-alpha-羧酸
  参考文献：
  名称：

  通过Aza-Prins环化的简明和非对映选择性合成哌啶和吲哚并立定生物碱

  摘要：

  2-取代和2,4-二取代哌啶生物碱的合成，例如（±）-con氨酸，（±）-羟基哌酸，（±）-哌酸，（±）-癸酸和（±）-4-羟基通过采用氮杂-Prins环化作为构建这些生物碱的哌啶核心的关键步骤，以高度非对映选择性的方式完成了-2-羟甲基哌啶。 aza-Prins环化-非对映选择性-哌啶-生物碱-天然产物

  DOI：

  10.1055/s-0031-1289648
• 作为产物：
  描述：

  2-哌啶甲醛,1-[(4-甲基苯基)磺酰]- 在 ruthenium trichloride sodium periodate 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 反应 18.0h， 以72%的产率得到1-(4-methylbenzenesulfonyl)pipecolic acid
  参考文献：
  名称：

  Ketene-S,S-acetals as 1,3-dipolarophiles towards azides. A new synthetic entry into cyclic amino acids

  摘要：

  Intramolecular azide cycloaddition reactions of ketene-S,S-acetals proceed to give a reactive imine as the initially-formed intermediate and this mechanism is supported by thermolysis of (18) which gave the stable imine (22). N-Acylation of this intermediate leads to cyclic variants of 2-amino ketene-S,S-acetals (20, 24, 27), which can be viewed as masked alpha-amino acids, and reduction leads to the corresponding dithiane (21, 25, 29a). Both systems have been converted to cyclic alpha-amino acids and the scope, in terms of the ring sizes available, and the limitations of this intramolecular cycloaddition process are discussed.

  DOI：

  10.1016/s0040-4020(01)90368-0

文献信息

• Nitrilase-Catalyzed Enantioselective Synthesis of Pyrrolidine- and Piperidinecarboxylic Acids
  作者：Margit Winkler、Dorith Meischler、Norbert Klempier

  DOI：10.1002/adsc.200700040

  日期：2007.6.4

  The enantioselective synthesis of the non-proteinogenic amino acids β-proline and nipecotic acids from their readily available nitriles is achieved in high enantiomeric excess by commercially available nitrilases. The presented procedure comprises not more than 4 steps, thus considerably reducing the multiple steps generally required. Amide formation is also observed for specific heterocyclic nitriles

  非蛋白源性氨基酸β-脯氨酸和乳糜酸从它们容易获得的腈中的对映选择性合成是通过市售腈水解酶以高对映体过量实现的。提出的过程包括不超过4个步骤，因此大大减少了通常需要的多个步骤。对于特定的杂环腈，也观察到酰胺的形成。
• HTE- and AI-assisted development of DHP-catalyzed decarboxylative selenation
  作者：Zhunzhun Yu、Yaxian Kong、Baiqing Li、Shimin Su、Jianhang Rao、Yadong Gao、Tianyong Tu、Hongming Chen、Kuangbiao Liao

  DOI：10.1039/d2cc06217h

  日期：——

  1,4-Dihydropyridine (DHP) derivatives play key roles in biology, but are rarely used as catalysts in synthesis.

  1,4-二氢吡啶（DHP）衍生物在生物学中扮演关键角色，但很少被用作合成催化剂。
• 10.1021/acs.orglett.4c02589
  作者：Yuan, Mingyue、Lou, Mingliang、Li, Gen、Qi, Xiangbing

  DOI：10.1021/acs.orglett.4c02589

  日期：——

  The decarboxylation of naturally abundant amino acids, followed by subsequent inter- or intramolecular reaction cascades, enables the rapid synthesis of a variety of diverse and high-value amine derivatives. Previous methods have relied heavily on transition metals, involved tedious procedures, or required harsh conditions. Herein, we present a novel reaction cascade for the decarboxylation and nucleophilic

  天然丰富的氨基酸脱羧，随后进行分子间或分子内级联反应，能够快速合成各种不同的高价值胺衍生物。以前的方法严重依赖过渡金属，涉及繁琐的程序或需要恶劣的条件。在此，我们提出了一种用于 α-氨基酸脱羧和亲核功能化的新型反应级联。该方法具有不含过渡金属、操作方便、环境友好、条件温和的特点。
• Peptidyl aldehyde inhibitors of calpain incorporating P2-proline mimetics
  作者：Isaac O. Donkor、Rajani Korukonda、Tien L. Huang、Louis LeCour

  DOI：10.1016/s0960-894x(03)00021-0

  日期：2003.3

  Four new peptidyl aldehydes bearing proline mimetics at the P-2-Position were synthesized and studied as inhibitors of calpain 1, cathepsin B, and selected serine proteases. The ring size of the P-2-constraining residue influenced the inhibitory potency and selectivity of the compounds for calpain I compared to the other proteases. (C) 2003 Elsevier Science Ltd. All rights reserved.
• A Concise and Diastereoselective Synthesis of Piperidine and Indolizidine Alkaloids via Aza-Prins Cyclization
  作者：Basi Reddy、Dudhmal Chaya、Jhillu Yadav、René Grée

  DOI：10.1055/s-0031-1289648

  日期：2012.1

  The synthesis of 2-substituted and 2,4-disubstituted piperidine alkaloids such as (±)-coniine, (±)-hydroxypipecolic acid, (±)-pipecolic acid, (±)-coniceine, and (±)-4-hydroxy-2-hydroxy­methyl piperidine have been accomplished in a highly diastereo­selective manner by employing aza-Prins cyclization as a key step to construct the piperidine core of these alkaloids. aza-Prins cyclization - diastereoselective

  2-取代和2,4-二取代哌啶生物碱的合成，例如（±）-con氨酸，（±）-羟基哌酸，（±）-哌酸，（±）-癸酸和（±）-4-羟基通过采用氮杂-Prins环化作为构建这些生物碱的哌啶核心的关键步骤，以高度非对映选择性的方式完成了-2-羟甲基哌啶。 aza-Prins环化-非对映选择性-哌啶-生物碱-天然产物