(1S,4S)-N-(2,4-dimethylphenyl)-(2-keto-7,7-dimethylbicyclo[2.2.1]hept-1-yl)methanesulfonamide | 1239861-59-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1S,4S)-N-(2,4-dimethylphenyl)-(2-keto-7,7-dimethylbicyclo[2.2.1]hept-1-yl)methanesulfonamide
• 英文别名: 1-[(1S,4R)-7,7-dimethyl-2-oxo-1-bicyclo[2.2.1]heptanyl]-N-(2,4-dimethylphenyl)methanesulfonamide
• CAS: 1239861-59-6
• 化学式: C₁₈H₂₅NO₃S
• 分子量: 335.467
• InChiKey: GTZRDUKQUNSTLZ-RDTXWAMCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,4S)-N-(2,4-dimethylphenyl)-(2-keto-7,7-dimethylbicyclo[2.2.1]hept-1-yl)methanesulfonamide 在 L-Selectride 作用下， 以 四氢呋喃 为溶剂， 以94.9%的产率得到(1S,2R,4S)-N-(2,4-dimethylphenyl)-(2-hydroxy-7,7-dimethylbicyclo[2.2.1]hept-1-yl)methanesulfonamide
  参考文献：
  名称：

  Synthesis, structure and activity of sulfonamides derived from (+)-camphor in the enantioselective addition of diethylzinc to benzaldehyde

  摘要：

  New chiral sulfonamides derived from (+)-camphor, with different substituents on camphor C2 and sulfonamide N, were synthesized. Their activity was tested in the reaction of Et2Zn addition to benzaldehyde. The yield of the reaction was 44-96%, the enantiomeric excess was 1-69%. Sulfonamides possessing the 2-hydroxyl group gave an excess of 1-(S)-phenylpropanol, while catalysts containing other sulfonamides gave 1-(R)-phenylpropanol as a major product. The best catalytic efficacy was observed for sulfonamides with (R)-C2-OH group, while the use of thioketo- and mercaptosulfonamides resulted in low enantiomeric excess and yields not exceeding 60%. Crystal structures have been determined for sulfonamides with N-benzyl moiety and different substituents on the C2 atom. The structural analysis revealed the presence of intramolecular N center dot center dot center dot O(C2) and O-sulfo center dot center dot center dot O(C2)H-bonds, what confirms the ability of these molecules to adopt the conformation required for their bidentate coordination to Ti(IV) via the sulfonamide group and substituent at C2. The coordination mode for investigated sulfonamides was determined with the IR spectra for five obtained Ti(IV) complexes and crystal structure analysis of the ligands. The 3D structures of Ti(IV) complex catalysts containing investigated sulfonamides were postulated, which are consistent with the reported chirality of the addition product and observed % ee. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2010.04.019
• 作为产物：
  描述：

  右旋樟脑-10-磺酰氯 、 2,4-二甲基苯胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以55.6%的产率得到(1S,4S)-N-(2,4-dimethylphenyl)-(2-keto-7,7-dimethylbicyclo[2.2.1]hept-1-yl)methanesulfonamide
  参考文献：
  名称：

  Synthesis, structure and activity of sulfonamides derived from (+)-camphor in the enantioselective addition of diethylzinc to benzaldehyde

  摘要：

  New chiral sulfonamides derived from (+)-camphor, with different substituents on camphor C2 and sulfonamide N, were synthesized. Their activity was tested in the reaction of Et2Zn addition to benzaldehyde. The yield of the reaction was 44-96%, the enantiomeric excess was 1-69%. Sulfonamides possessing the 2-hydroxyl group gave an excess of 1-(S)-phenylpropanol, while catalysts containing other sulfonamides gave 1-(R)-phenylpropanol as a major product. The best catalytic efficacy was observed for sulfonamides with (R)-C2-OH group, while the use of thioketo- and mercaptosulfonamides resulted in low enantiomeric excess and yields not exceeding 60%. Crystal structures have been determined for sulfonamides with N-benzyl moiety and different substituents on the C2 atom. The structural analysis revealed the presence of intramolecular N center dot center dot center dot O(C2) and O-sulfo center dot center dot center dot O(C2)H-bonds, what confirms the ability of these molecules to adopt the conformation required for their bidentate coordination to Ti(IV) via the sulfonamide group and substituent at C2. The coordination mode for investigated sulfonamides was determined with the IR spectra for five obtained Ti(IV) complexes and crystal structure analysis of the ligands. The 3D structures of Ti(IV) complex catalysts containing investigated sulfonamides were postulated, which are consistent with the reported chirality of the addition product and observed % ee. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2010.04.019

文献信息

• Synthesis, structure and activity of sulfonamides derived from (+)-camphor in the enantioselective addition of diethylzinc to benzaldehyde
  作者：Anna Kozakiewicz、Małgorzata Ullrich、Mirosław Wełniak、Andrzej Wojtczak

  DOI：10.1016/j.molcata.2010.04.019

  日期：2010.7

  New chiral sulfonamides derived from (+)-camphor, with different substituents on camphor C2 and sulfonamide N, were synthesized. Their activity was tested in the reaction of Et2Zn addition to benzaldehyde. The yield of the reaction was 44-96%, the enantiomeric excess was 1-69%. Sulfonamides possessing the 2-hydroxyl group gave an excess of 1-(S)-phenylpropanol, while catalysts containing other sulfonamides gave 1-(R)-phenylpropanol as a major product. The best catalytic efficacy was observed for sulfonamides with (R)-C2-OH group, while the use of thioketo- and mercaptosulfonamides resulted in low enantiomeric excess and yields not exceeding 60%. Crystal structures have been determined for sulfonamides with N-benzyl moiety and different substituents on the C2 atom. The structural analysis revealed the presence of intramolecular N center dot center dot center dot O(C2) and O-sulfo center dot center dot center dot O(C2)H-bonds, what confirms the ability of these molecules to adopt the conformation required for their bidentate coordination to Ti(IV) via the sulfonamide group and substituent at C2. The coordination mode for investigated sulfonamides was determined with the IR spectra for five obtained Ti(IV) complexes and crystal structure analysis of the ligands. The 3D structures of Ti(IV) complex catalysts containing investigated sulfonamides were postulated, which are consistent with the reported chirality of the addition product and observed % ee. (C) 2010 Elsevier B.V. All rights reserved.