Pyridine-2-sulfonic acid ((S)-1-naphthalen-1-yl-ethyl)-amide | 370839-71-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Pyridine-2-sulfonic acid ((S)-1-naphthalen-1-yl-ethyl)-amide
• 英文别名: N-[(1S)-1-naphthalen-1-ylethyl]pyridine-2-sulfonamide
• CAS: 370839-71-7
• 化学式: C₁₇H₁₆N₂O₂S
• 分子量: 312.392
• InChiKey: XWJDCJUZKOMKET-ZDUSSCGKSA-N

物化性质

• 沸点：
  517.4±52.0 °C(Predicted)
• 密度：
  1.273±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  67.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Pyridine-2-sulfonic acid ((S)-1-naphthalen-1-yl-ethyl)-amide 在 magnesium 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以90%的产率得到(S)-(-)-1-(1-萘基)乙胺
  参考文献：
  名称：

  DEPROTECTION OF 2-PYRIDYL SULFONYL GROUP FROM PYRIDINE-2-SULFONAMIDES BY MAGNESIUM IN METHANOL

  摘要：

  Convenient deprotection of various pyridine-2-sulfonamides prepared by sulfonylation of primary and secondary amines with pyridine-2-sulfonylchloride was achieved by magnesium in methanol at 0 degreesC to the corresponding amines in good yield.

  DOI：

  10.1081/scc-100104475
• 作为产物：
  描述：

  吡啶-2-磺酰氯 、 (S)-(-)-1-(1-萘基)乙胺 以92%的产率得到Pyridine-2-sulfonic acid ((S)-1-naphthalen-1-yl-ethyl)-amide
  参考文献：
  名称：

  DEPROTECTION OF 2-PYRIDYL SULFONYL GROUP FROM PYRIDINE-2-SULFONAMIDES BY MAGNESIUM IN METHANOL

  摘要：

  Convenient deprotection of various pyridine-2-sulfonamides prepared by sulfonylation of primary and secondary amines with pyridine-2-sulfonylchloride was achieved by magnesium in methanol at 0 degreesC to the corresponding amines in good yield.

  DOI：

  10.1081/scc-100104475

文献信息

• Enantioselective CC Bond Formation to Sulfonylimines through Use of the 2-Pyridinesulfonyl Group as a Novel Stereocontroller
  作者：Shuichi Nakamura、Hiroki Nakashima、Hideki Sugimoto、Hideaki Sano、Masataka Hattori、Norio Shibata、Takeshi Toru

  DOI：10.1002/chem.200701425

  日期：2008.2.27

  Enantioselective C--C bond formation to 2-pyridinesulfonylimines afforded products with good enantioselectivity. Dynamic induction of chirality on the sulfur by coordination of a chiral Lewis acid to the pyridine nitrogen and one of the prochiral sulfonyl oxygens induces enantioselectivity. Since the 2-pyridinesulfonyl group can easily be removed after the reaction, it acts not only as an activating

  对2-吡啶磺酰亚胺的对映选择性CC键形成提供具有良好对映选择性的产物。通过手性路易斯酸与吡啶氮和前手性磺酰基氧之一的配位，在硫上动态诱导手性，诱导对映选择性。由于2-吡啶磺酰基在反应后可以容易地除去，因此它不仅起活化基团的作用，而且起有效的立体调节剂的作用。
• Enantioselective nucleophilic addition to N-(2-pyridylsulfonyl)imines by use of dynamically induced chirality
  作者：Hideki Sugimoto、Shuichi Nakamura、Masataka Hattori、Sachiko Ozeki、Norio Shibata、Takeshi Toru

  DOI：10.1016/j.tetlet.2005.10.085

  日期：2005.12

  Enantioselective nucleophilic addition of Grignard reagents to N-(2-pyridylsulfonyl)imines in the presence of bis(oxazoline) afforded products with good enantioselectivity. Dynamically induced chirality on the sulfur by coordination of a chiral Lewis acid to a pyridyl nitrogen and one of the sulfonyl oxygens fixes the conformation of the complex and induces enantioselectivity. Since the 2-pyridylsulfonyl

  在双（恶唑啉）存在下，将格氏试剂对N-（2-吡啶基磺酰基）亚胺的对映选择性亲核加成得到具有良好对映选择性的产物。通过手性路易斯酸与吡啶基氮和一种磺酰基氧的配位，在硫上动态诱导的手性可固定配合物的构象并诱导对映选择性。由于2-吡啶基磺酰基在加成反应后可以容易地除去，因此它不仅起保护基的作用，而且起有效的立体调节剂的作用。
• DEPROTECTION OF 2-PYRIDYL SULFONYL GROUP FROM PYRIDINE-2-SULFONAMIDES BY MAGNESIUM IN METHANOL
  作者：Chwang Siek Pak、Dong Sung Lim

  DOI：10.1081/scc-100104475

  日期：2001.1.1

  Convenient deprotection of various pyridine-2-sulfonamides prepared by sulfonylation of primary and secondary amines with pyridine-2-sulfonylchloride was achieved by magnesium in methanol at 0 degreesC to the corresponding amines in good yield.