(R)-N-[(4-trifluoromethylphenyl)phenylmethyl]-4-methylbenzenesulfonamide

• 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: (R)-N-[(4-trifluoromethylphenyl)phenylmethyl]-4-methylbenzenesulfonamide
• 英文别名: (R)-4-methyl-N-((phenyl(4-trifluoromethyl)phenyl)methyl)benzenesulfonamide；4-methyl-N-[(R)-phenyl-[4-(trifluoromethyl)phenyl]methyl]benzenesulfonamide
• 化学式: C₂₁H₁₈F₃NO₂S
• 分子量: 405.441
• InChiKey: YLNWQJKVDLQZMV-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  三甲基(苯基)锡 在 4-二甲氨基吡啶 、 bis(ethylene)rhodium acetylacetonate 、 (R)-[2'-(3,5-Me₂-4-MeO-C₆H₂)-2-(Ph₂)P]-1,1'-binaphthyl 、 potassium carbonate 、 苯硫酚 、 lithium fluoride 、 三乙胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 41.0h， 生成 (R)-N-[(4-trifluoromethylphenyl)phenylmethyl]-4-methylbenzenesulfonamide
  参考文献：
  名称：

  铑催化的亚胺与有机锡烷的不对称芳基化。二芳基甲胺的不对称合成

  摘要：

  DOI：

  10.1021/ja9927220

文献信息

• Rhodium-Catalyzed Asymmetric Addition of Organoboronic Acids to Aldimines Using Chiral Spiro Monophosphite-Olefin Ligands: Method Development and Mechanistic Studies
  作者：Huanyu Shan、Qiaoxia Zhou、Jinglu Yu、Shuoqing Zhang、Xin Hong、Xufeng Lin

  DOI：10.1021/acs.joc.8b01764

  日期：2018.10.5

  on a hexamethyl-1,1′-spirobiindane scaffold was accomplished starting from Bisphenol C. The optimal ligand could serve as an elegant chiral bidentate ligand in the Rh-catalyzed asymmetric 1,2-addition of organoboronic acids to various acyclic/cyclic aldimines, leading to chiral amines with high yields and excellent enantioselectivities. Detailed stereochemical models for enantioselective induction

  从双酚C开始合成基于六甲基-1,1'-螺双茚满骨架的新型手性螺一亚磷酸酯-烯烃（SMPO）配体。最佳配体可作为Rh-中的优雅手性双齿配体催化有机硼酸向各种无环/环状醛亚胺的不对称1,2-加成反应，从而获得具有高收率和优异对映选择性的手性胺。通过DFT计算阐明了对映选择性诱导的详细立体化学模型，并假定了亚磷酸酯-烯烃配体具有较高对映选择性的起源。
• 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。
• Design and synthesis of new chiral phosphorus–olefin bidentate ligands and their use in the rhodium-catalyzed asymmetric addition of organoboroxines to N-sulfonyl imines
  作者：Ryo Shintani、Rintaro Narui、Yosuke Tsutsumi、Sayuri Hayashi、Tamio Hayashi

  DOI：10.1039/c1cc11823d

  日期：——

  Novel chiral phosphorus-olefin bidentate ligands have been synthesized in a few steps from a readily available enantiopure compound. These ligands have been applied to a rhodium-catalyzed asymmetric addition of organoboroxines to N-sulfonyl aldimines, achieving high yield and enantioselectivity.

  新型的手性磷-烯烃双齿配体已由易于获得的对映纯化合物经数步合成。这些配体已被用于铑催化的将有机硼氧烷酮不对称加成到N-磺酰基醛亚胺上，从而实现了高收率和对映选择性。
• Rh(I)-Catalyzed Asymmetric Synthesis of 3-Substituted Isoindolinones through CO Gas-Free Aminocarbonylation
  作者：Masahiko Fujioka、Tsumoru Morimoto、Takayuki Tsumagari、Hiroki Tanimoto、Yasuhiro Nishiyama、Kiyomi Kakiuchi

  DOI：10.1021/jo300201g

  日期：2012.3.16

  A highly efficient and accessible synthesis of chiral 3-substituted isoindolinone frameworks is described. The synthesis involved the Rh(I)-catalyzed asymmetric arylation of boronic acids to 2-halobenzaldimines and the subsequent Rh(I)-catalyzed intramolecular aminocarbonylation of the resulting 2-halobenzylamines using an aldehyde as the carbonyl source. The method tolerates a variety of functional

  描述了手性3-取代的异吲哚满酮骨架的高效且容易获得的合成。合成涉及硼酸经Rh（I）催化的不对称芳基化成2-卤代苯丙二胺，随后使用醛作为羰基源，经Rh（I）催化的所得2-卤代苄胺的分子内氨基羰基化。该方法可耐受多种官能团，以中等至高收率和高ee值产生异吲哚啉酮衍生物。另外，通过在Rh（I）催化的不对称芳基化之后简单地添加配体和醛，可以在一个锅序列中有效地完成两个Rh（I）催化的转化，以得到手性异吲哚啉酮。
• <i>C</i>₂-Symmetric Bicyclo[2.2.2]octadienes as Chiral Ligands:  Their High Performance in Rhodium-Catalyzed Asymmetric Arylation of <i>N</i>-Tosylarylimines
  作者：Norihito Tokunaga、Yusuke Otomaru、Kazuhiro Okamoto、Kazuhito Ueyama、Ryo Shintani、Tamio Hayashi

  DOI：10.1021/ja044790e

  日期：2004.10.1

  Asymmetric synthesis of diarylmethylamines with high enantioselectivity (95-99% ee) was realized by use of a new C2-symmetric diene ligand, (1R,4R)-2,5-diphenylbicyclo[2.2.2]octa-2,5-diene (Ph-bod*), for the rhodium-catalyzed asymmetric arylation of N-tosylarylimines with arylboroxines.