(R)-N-[(1-naphthyl)phenylmethyl]-4-methylbenzenesulfonamide | 66558-07-4

• 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-[(1-naphthyl)phenylmethyl]-4-methylbenzenesulfonamide
• 英文别名: (R)-4-methyl-N-(naphthalen-1-yl(phenyl)methyl)benzenesulfonamide；(R)-N-tosyl-α-(1-naphthyl)benzylamine；4-methyl-N-[(R)-naphthalen-1-yl(phenyl)methyl]benzenesulfonamide
• CAS: 66558-07-4
• 化学式: C₂₄H₂₁NO₂S
• 分子量: 387.502
• InChiKey: OPVXSDSXZSCYRO-XMMPIXPASA-N

物化性质

• 熔点：
  162.4-162.9 °C
• 沸点：
  583.0±60.0 °C(Predicted)
• 密度：
  1.230±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-N-[(1-naphthyl)phenylmethyl]-4-methylbenzenesulfonamide 在 六甲基磷酰三胺 、 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以74%的产率得到(R)-α-(1-naphthyl)benzylamine
  参考文献：
  名称：

  Enantioselective Rh-Catalyzed Arylation of N-Tosylarylimines with Arylboronic Acids

  摘要：

  The asymmetric arylation of N-tosylarylimines with arylboronic acids was realized by using rhodium/(S)-ShiP as catalyst. The reaction proceeded in aqueous toluene to give diarylmethylamines in good yields with up to 96% ee.

  DOI：

  10.1021/ol060755w
• 作为产物：
  描述：

  (1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate 在 lithium aluminium tetrahydride 、 1-氯苯并三氮唑 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 30.0h， 生成 (R)-N-[(1-naphthyl)phenylmethyl]-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Annunziata, Rita; Cinquini, Mauro; Cozzi, Franco, Journal of the Chemical Society. Perkin transactions I, 1982, p. 339 - 344

  摘要：

  DOI：

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。
• Pd(II)/(S)-t-BuPyOx-catalyzed asymmetric addition of arylboronic acids to N-sulfonyl-arylaldimines
  作者：Kaixuan Song、Min Wen、Kai Shen、Chaogang Fan、Zhenyu Yang、Shaohui Lin、Qinmin Pan

  DOI：10.1016/j.tetlet.2021.153057

  日期：2021.5

  The asymmetric version of Pd(II)/bipyridine-catalyzed nucleophilic addition of arylboronic acids to N-sulfonyl arylaldimines was developed, and excellent asymmetric induction was achieved by the use of chiral pyridinooxazoline ligand (S)-t-BuPyOx. Moisture and oxygen-insensitive catalysis was realized under mild conditions, and 9 out of 16 examples gave 92–99% ee.

  开发了不对称形式的Pd（II）/联吡啶催化的芳基硼酸向N-磺酰基芳基醛亚胺的亲核加成反应，并且通过使用手性吡啶并恶唑啉配体（S）-t- BuPyOx实现了出色的不对称诱导。在温和的条件下实现了对水分和氧气不敏感的催化作用，在16个实例中有9个产生了92-99％ee。
• Chiral benzene backbone-based sulfoxide-olefin ligands for highly enantioselective Rh-catalyzed addition of arylboronic acids to <i>N</i>-tosylarylimines
  作者：Feng Xue、Qibin Liu、Yong Zhu、Yunfei Qing、Boshun Wan

  DOI：10.1039/c9ra04836g

  日期：——

  An efficient Rh-catalyzed addition of arylboronic acids to N-tosylarylimines has been developed with chiral benzene backbone-based sulfoxide-olefin ligands, where 2-methoxy-1-naphthyl sulfinyl functionalized olefin ligands have shown to be more effective. The versatile method tolerates a wide range of functional groups and shows broad scope without regard to electronic or steric substitution pattern

  已经使用基于手性苯骨架的亚砜-烯烃配体开发了一种高效的 Rh 催化芳基硼酸加成到N-甲苯磺酰基亚胺，其中 2-甲氧基-1-萘基亚磺酰基官能化烯烃配体已显示更有效。这种通用方法可耐受多种官能团，并且在不考虑电子或空间取代模式的情况下显示出广泛的范围，允许以高产率（高达 99%）获得范围广泛的手性二芳基甲胺，并具有出色的对映选择性（高达 99% ee ）。