4-chloro-1,2,5,6-tetrahydro-1-tosylpyridine | 575501-45-0

• 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: 4-chloro-1,2,5,6-tetrahydro-1-tosylpyridine
• 英文别名: 4-chloro-1-tosyl-1,2,3,6-tetrahydropyridine；4-chloro-1-(4-methylphenyl)sulfonyl-3,6-dihydro-2H-pyridine
• CAS: 575501-45-0
• 化学式: C₁₂H₁₄ClNO₂S
• 分子量: 271.768
• InChiKey: UIKZITZMMGQCGS-UHFFFAOYSA-N

物化性质

• 沸点：
  407.9±55.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-chloro-1,2,5,6-tetrahydro-1-tosylpyridine 、 苯硼酸 在 potassium phosphate 、 dicyclohexyl(2,4,6-trimethoxyphenyl)phosphonium tetrafluoroborate 、 palladium diacetate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 12.0h， 以85%的产率得到4-phenyl-1-tosyl-1,2,3,6-tetrahydropyridine
  参考文献：
  名称：

  FeCl3-catalyzed cyclization of α-sulfonamido-allenes with aldehydes—the substituent effect

  摘要：

  在 FeCl3 催化下，δ-磺酰胺基亚庚烯与醛的氮杂-普林环化反应高效且高选择性地生成了 1,2,3,6- 四氢吡啶或 2,5- 二氢-1H-吡咯衍生物。不同的区域选择性可能是由于苯基对带正电荷的烯丙基中间体的稳定作用造成的。

  DOI：

  10.1039/c2cc36941a
• 作为产物：
  描述：

  4-methyl-N-(3-oxopropyl)benzenesulfonamide 在 三氯化铁 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.17h， 生成 4-chloro-1,2,5,6-tetrahydro-1-tosylpyridine
  参考文献：
  名称：

  Iron(III)-Promoted Aza-Prins-Cyclization:  Direct Synthesis of Six-Membered Azacycles

  摘要：

  A new iron(III) halide-promoted aza-Prins cyclization between gamma,delta-unsaturated tosylamines and aldehydes provides six-membered azacycles in good to excellent yields. The process is based on the consecutive generation of gamma-unsaturated-iminium ion and further nucleophilic attack by the unsaturated carbon-carbon bond. Homoallyl tosylamine leads to trans-2-alkyl-4-halo-1-tosylpiperidine as the major isomer. In addition, the alkyne aza-Prins cyclization between homopropargyl tosylamine and aldehydes gives 2-alkyl-4-halo-1-tosyl-1,2,5,6-tetrahydropyridines as the only cyclic products.

  DOI：

  10.1021/ol061448t

文献信息

• Suzuki-Miyaura coupling of heteroaryl boronic acids and vinyl chlorides
  作者：Ashish Thakur、Kainan Zhang、Janis Louie

  DOI：10.1039/c1cc15990a

  日期：——

  A protocol for the Suzuki-Miyaura coupling of heteroaryl boronic acids and vinyl chlorides that minimizes protodeboronation is described. A combination of catalytic amounts of Pd(OAc)(2) and SPhos in conjunction with CsF in isopropanol effectively affords a variety of coupled products. Surprisingly, a dramatic temperature dependence in product selectivity was observed.

  描述了用于杂芳基硼酸和氯乙烯的Suzuki-Miyaura偶联的方案，其使原去硼烷化最小化。异丙醇中催化量的Pd（OAc）（2）和SPhos与CsF的组合可有效提供多种偶联产物。令人惊讶地，观察到产物选择性中显着的温度依赖性。
• The First Examples of Ring-Closing Olefin Metathesis of Vinyl Chlorides
  作者：Wenchun Chao、Steven M. Weinreb

  DOI：10.1021/ol034775z

  日期：2003.7.1

  [GRAPHICS]Ring-closing metathesis (RCM) of olefinic vinyl chlorides can be effected by using the second generation Grubbs catalyst (10 mol %, PhH, 65degreesC) to produce a variety of carbocyclic and heterocyclic five-, six-, and seven-membered rings in excellent yields.
• Antiproliferative activity of 2-alkyl-4-halopiperidines and 2-alkyl-4-halo-1,2,5,6-tetrahydropyridines in solid tumor cell lines
  作者：Leticia G. León、Rubén M. Carballo、María C. Vega-Hernández、Víctor S. Martín、Juan I. Padrón、José M. Padrón

  DOI：10.1016/j.bmcl.2007.03.010

  日期：2007.5

  A series of trans-2-alkyl-4-halopiperidines and 2-alkyl-4-halo-1,2,5,6-tetrahydropyridines were prepared by means of an iron(III) catalyzed process. The in vitro antiproliferative activities were examined in the human solid tumor cell lines A2780 (ovarian cancer), SW1573 (non-small cell lung cancer), and WiDr (colon cancer). The results on the biological activity revealed that, in general, the 2-alkyl-4-halo-1,2,5,6-tetrahydropyridine analogs are more potent than the trans-2-alkyl-4-halopiperidine derivatives. A remarkable selectivity of the aza compound 5f for the resistant cell line WiDr was observed. Cell cycle studies revealed a G(2)/M phase arrest for 5f. (c) 2007 Elsevier Ltd. All rights reserved.
• FeCl3-catalyzed cyclization of α-sulfonamido-allenes with aldehydes—the substituent effect
  作者：Jiajia Cheng、Xinjun Tang、Yihua Yu、Shengming Ma

  DOI：10.1039/c2cc36941a

  日期：——

  FeCl3-catalyzed aza-Prins-cyclization reaction of α-sulfonamido-allenes with aldehydes afforded 1,2,3,6-tetrahydropyridine or 2,5-dihydro-1H-pyrrole derivatives efficiently and highly selectively. The different regioselectivity is probably caused by the stabilizing effect of the phenyl group on the positively charged allylic intermediate.

  在 FeCl3 催化下，δ-磺酰胺基亚庚烯与醛的氮杂-普林环化反应高效且高选择性地生成了 1,2,3,6- 四氢吡啶或 2,5- 二氢-1H-吡咯衍生物。不同的区域选择性可能是由于苯基对带正电荷的烯丙基中间体的稳定作用造成的。
• Iron(III)-Promoted Aza-Prins-Cyclization:  Direct Synthesis of Six-Membered Azacycles
  作者：Rubén M. Carballo、Miguel A. Ramírez、Matías L. Rodríguez、Víctor S. Martín、Juan I. Padrón

  DOI：10.1021/ol061448t

  日期：2006.8.1

  A new iron(III) halide-promoted aza-Prins cyclization between gamma,delta-unsaturated tosylamines and aldehydes provides six-membered azacycles in good to excellent yields. The process is based on the consecutive generation of gamma-unsaturated-iminium ion and further nucleophilic attack by the unsaturated carbon-carbon bond. Homoallyl tosylamine leads to trans-2-alkyl-4-halo-1-tosylpiperidine as the major isomer. In addition, the alkyne aza-Prins cyclization between homopropargyl tosylamine and aldehydes gives 2-alkyl-4-halo-1-tosyl-1,2,5,6-tetrahydropyridines as the only cyclic products.