(S)-N-[(4-methoxyphenyl)phenylmethyl]-4-nitrobenzenesulfonamide | 840529-68-2

• 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: (S)-N-[(4-methoxyphenyl)phenylmethyl]-4-nitrobenzenesulfonamide
• 英文别名: (S)-N-[phenyl(4-methoxyphenyl)methyl]-4-nitrobenzenesulfonamide；N-[(S)-(4-methoxyphenyl)(phenyl)methyl]-4-nitrobenzenesulfonamide；N-[(S)-(4-methoxyphenyl)-phenylmethyl]-4-nitrobenzenesulfonamide
• CAS: 840529-68-2
• 化学式: C₂₀H₁₈N₂O₅S
• 分子量: 398.439
• InChiKey: LPULIIWVTCZFHV-FQEVSTJZSA-N

物化性质

• 熔点：
  220-222 °C
• 沸点：
  597.3±60.0 °C(Predicted)
• 密度：
  1.326±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-N-[(4-methoxyphenyl)phenylmethyl]-4-nitrobenzenesulfonamide 在 potassium carbonate 、 4-甲苯硫酚 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-(4-methoxyphenyl)(phenyl)methanamine
  参考文献：
  名称：

  铑通过手性双环[3.3.0]二烯配体的铑催化的N- Nosylimines的芳基化反应高选择性合成（二芳基甲基）胺

  摘要：

  描述了由铑-二烯络合物催化的N- nosylimines与芳基硼酸的高效不对称芳基化 。以高收率获得了多种对映纯（98-99％ee）N-（二芳基甲基）壬酰胺以及（3 S）-2-（4-壬基）-3-苯基异吲哚啉-1-酮（83 -99％）。 不对称催化-胺-芳基化-铑-二芳基甲胺

  DOI：

  10.1055/s-0030-1258210
• 作为产物：
  描述：

  N-(4-methoxyphenyl)methylidene-4-nitrobenzenesulfonamide 、 苯硼酸酐 在 [RhCl((1R,5R)-2,6-diphenylbicyclo[3.3.1]nona-2,6-diene)]2 氢氧化钾 作用下， 以 1,4-二氧六环 为溶剂， 反应 6.0h， 以98%的产率得到(S)-N-[(4-methoxyphenyl)phenylmethyl]-4-nitrobenzenesulfonamide
  参考文献：
  名称：

  C₂-Symmetric Bicyclo[3.3.1]nonadiene as a Chiral Ligand for Rhodium-Catalyzed Asymmetric Arylation of N-(4-Nitrobenzenesulfonyl)arylimines

  摘要：

  Asymmetric synthesis of diarylmethylamines with high enantioselectivity (95-99% ee) was realized by use of a new C-2-symmetric diene ligand. (1R,5R)-2,6-diphenylbicyclo[3.3.1]nona-2,6-diene (Ph-bnd*), for the rhodium-catalyzed asymmetric arylation of N(4-nitrobenzenesulfony)arylimines with arylboroxines.

  DOI：

  10.1021/ol0476063

文献信息

• Electronic and steric tuning of chiral diene ligands for rhodium-catalyzed asymmetric arylation of imines
  作者：Kazuhiro Okamoto、Tamio Hayashi、Viresh H. Rawal

  DOI：10.1039/b904624k

  日期：——

  Rhodium-catalyzed asymmetric arylation of imines using electronically and sterically-modified chiral diene ligands gave the corresponding diarylmethylamines in high yield and with high enantioselectivity using just 0.3 mol% of catalyst.

  使用电子和空间改性的手性二烯配体，铑催化的亚胺的不对称芳基化仅使用0.3 mol％的催化剂就可以高收率和高对映选择性地得到相应的二芳基甲胺。
• An N-Linked Bidentate Phosphoramidite Ligand (N-Me-BIPAM) for Rhodium-Catalyzed Asymmetric Addition of Arylboronic Acids to N-Sulfonylarylaldimines
  作者：Kazunori Kurihara、Yasunori Yamamoto、Norio Miyaura

  DOI：10.1002/adsc.200800631

  日期：2009.1

  A chiral N-linked C2-symmetric bidentate phosphoramidite (N-Me-BIPAM) was newly developed for the rhodium-catalyzed enantioselective addition of arylboronic acids to N-sulfonylimines. This ligand achieved high enantioselectivities in a range of 84–99% ee in additions of arylboronic acids to N-tosyl- and N-nosylarylaldimines.

  手性N-连接的C 2-对称的二齿亚磷酰胺（N -Me-BIPAM）是新开发的，用于铑催化的对N-磺酰亚胺基的芳基硼酸的对映选择性加成。除了在N-甲苯磺酰基和N-壬基芳基醛亚胺中添加芳基硼酸外，该配体还实现了84-99％ee范围内的高对映选择性。
• Rhodium-Catalyzed Asymmetric Arylation of Imines with Organostannanes. Asymmetric Synthesis of Diarylmethylamines
  作者：Tamio Hayashi、Mitsuo Ishigedani

  DOI：10.1021/ja9927220

  日期：2000.2.1
• Highly Enantioselective Synthesis of (Diarylmethyl)amines by Rhodium-Catalyzed­ Arylation of N-Nosylimines Using a Chiral Bicyclo[3.3.0]diene Ligand
  作者：Ming-Hua Xu、Guo-Qiang Lin、Li Wang、Zhi-Qian Wang

  DOI：10.1055/s-0030-1258210

  日期：2010.10

  A highly efficient asymmetric arylation of N-nosylimines with arylboronic acids catalyzed by a rhodium-diene complex is described. A wide range of enantiopure (98-99% ee) N-(diarylmethyl)nosylamides, as well as (3S)-2-(4-nosyl)-3-phenylisoindolin-1-one, were obtained in high yields (83-99%) under very mild conditions. asymmetric catalysis - amines - arylations - rhodium - diarylmethylamines

  描述了由铑-二烯络合物催化的N- nosylimines与芳基硼酸的高效不对称芳基化 。以高收率获得了多种对映纯（98-99％ee）N-（二芳基甲基）壬酰胺以及（3 S）-2-（4-壬基）-3-苯基异吲哚啉-1-酮（83 -99％）。 不对称催化-胺-芳基化-铑-二芳基甲胺
• <i>C</i>₂-Symmetric Bicyclo[3.3.1]nonadiene as a Chiral Ligand for Rhodium-Catalyzed Asymmetric Arylation of <i>N</i>-(4-Nitrobenzenesulfonyl)arylimines
  作者：Yusuke Otomaru、Norihito Tokunaga、Ryo Shintani、Tamio Hayashi

  DOI：10.1021/ol0476063

  日期：2005.1.1

  Asymmetric synthesis of diarylmethylamines with high enantioselectivity (95-99% ee) was realized by use of a new C-2-symmetric diene ligand. (1R,5R)-2,6-diphenylbicyclo[3.3.1]nona-2,6-diene (Ph-bnd*), for the rhodium-catalyzed asymmetric arylation of N(4-nitrobenzenesulfony)arylimines with arylboroxines.