N-(2-hydroxy-1,2-diphenylethyl)-4-methylbenzenesulfonamide | 3316-42-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: N-(2-hydroxy-1,2-diphenylethyl)-4-methylbenzenesulfonamide
• 英文别名: anti-1,2-diphenyl-2-(tosylamino)ethanol；syn-1,2-diphenyl-2-(tosylamino)ethanol；Ts-DPEN；2-(p-Tosylamino)-1,2-diphenyl-aethanol
• CAS: 3316-42-5
• 化学式: C₂₁H₂₁NO₃S
• 分子量: 367.469
• InChiKey: URVQPPFOCBAUNE-UHFFFAOYSA-N

物化性质

• 熔点：
  204 °C(Solv: ethanol (64-17-5))
• 沸点：
  548.3±60.0 °C(Predicted)
• 密度：
  1.253±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  74.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2-hydroxy-1,2-diphenylethyl)-4-methylbenzenesulfonamide 在 4 A molecular sieve 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 4-methyl-N-(2-oxo-1,2-diphenylethyl)benzene sulfonamide
  参考文献：
  名称：

  A general approach to polysubstituted pyrroles

  摘要：

  Exposure of a range of 3-hydroxy-2-sulfonylamino-4-alkynes to excess iodine delivers good yields of a series of iodopyrroles. Unexpectedly, the hydroxyl-dihydropyrroles, which were assumed to be the first-formed intermediates, turn out to be stable entities which have been isolated for the first time. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.08.097
• 作为产物：
  描述：

  4-methyl-N-(2-oxo-1,2-diphenylethyl)benzene sulfonamide 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以81%的产率得到N-(2-hydroxy-1,2-diphenylethyl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  碘（III）介导的胺的氧化重排：[小α]-氨基酮的有效合成

  摘要：

  碘（III）介导的小β，小β-二芳亚胺向小α-氨基酮的基团选择性氧化重排已经以优异的产率完成。发达的反应涉及烯胺最初氧化为[小α-酰氧基亚胺中间体和伴随的...

  DOI：

  10.1039/c5cc04265h
• 作为试剂：
  描述：

  ethyl 2-(tert-butoxycarbonylamino)-3-(3-chlorophenyl)-3-oxopropanoate 在 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 N-(2-hydroxy-1,2-diphenylethyl)-4-methylbenzenesulfonamide 、 甲酸:三乙胺 1:1 作用下， 以 异丙醇 为溶剂， 生成 (2S,3S)-ethyl 2-(tert-butoxycarbonylamino)-3-(3-chlorophenyl)-3-hydroxypropanoate
  参考文献：
  名称：

  Enantioselective Synthesis of anti-β-Hydroxy-α-amido Esters via Transfer Hydrogenation

  摘要：

  The asymmetric transfer hydrogenation of alpha-amido-beta-keto esters to provide the corresponding anti-beta-hydroxy-alpha-amido esters in good to excellent yields, diastereoselectivity, and enantioselectivity is reported. The procedure is operationally simple, and delicate handling of the catalyst is not necessary.

  DOI：

  10.1021/ol102323k

文献信息

• A Convenient and Highly Productive Aminohydroxylation Protocol Employing an Osmium-Diamine Catalyst
  作者：Kilian Muñiz、Iriux Almodovar、Jan Streuff、Martin Nieger

  DOI：10.1002/adsc.200606054

  日期：2006.9

  In situ generated osmium-diamine chelates from 2,3-diaminopropionic acid or diaminosuccinic acid represent efficient catalysts for the highly productive aminohydroxylation of alkenes. The reaction can be employed with various osmium salts and successful catalyst recycling was demonstrated for a representative example. The catalyst design derives from the general structural features of recently investigated

  由2，3-二氨基丙酸或二氨基琥珀酸原位生成的二胺螯合物代表了烯烃高产氨基羟基化的有效催化剂。该反应可以与各种盐一起使用，并且对于一个代表性的实例证明了成功的催化剂再循环。催化剂的设计源自烯烃烯化反应中最近研究的络合物的一般结构特征。
• Asymmetric Synthesis of <i>anti</i>- and <i>syn</i>-β-Amino Alcohols by Reductive Cross-Coupling of Transition Metal-Coordinated Planar Chiral Arylaldehydes with Aldimines
  作者：Yoshie Tanaka、Nobukazu Taniguchi、Takayuki Kimura、Motokazu Uemura

  DOI：10.1021/jo0205412

  日期：2002.12.1

  with planar chiral ferrocenecarboxaldehydes or benzaldehyde chromium complexes gave diastereoselectively the corresponding anti-beta-amino alcohol derivatives in good yields, while N-tosyl benzylideneamine produced syn-beta-amino alcohols by coupling with planar chiral arylaldehydes. Dynamic kinetic resolution of a configurationally equilibrated reactive species generated from achiral N-tosyl ferrocenilideneamine

  碘化mar介导的N-甲苯磺酰基亚铁亚胺与平面手性二茂铁甲醛或苯甲醛铬配合物的交叉偶联，非对映选择性地以高收率选择性地生成了相应的抗β-氨基醇衍生物，而N-甲苯磺酰基亚苄基胺通过与平面手性芳基醛。在与平面手性芳醛的交叉偶联中，观察到由手性N-甲苯磺酰亚铁亚胺和苄叉胺通过碘化reduction还原生成的构型平衡的反应物种的动态动力学拆分，这取决于平面手性，给出了β-氨基醇的两个对映体。所获得的具有二茂铁环的抗β-氨基醇用作手性配体，用于催化苯乙酮的不对称还原。
• Neighbouring group assisted sulfonamide cleavage of Sharpless aminols under acetonation conditions
  作者：S. Chandrasekhar、Suchismita Mohapatra

  DOI：10.1016/s0040-4039(97)10638-4

  日期：1998.2

  It is accidentally observed that N-Ts cleavage and simultaneous protection of resulting free amino group as acetonide with the adjacent hydroxy group is achieved in one pot. Neighbouring carboxylic ester group is essential for this transformation.

  偶然地观察到，在一锅中实现了N-Ts的裂解，并同时保护了作为丙酮化物的所得游离氨基与相邻的羟基。相邻的羧酸酯基对于该转化是必不可少的。
• NaHSO3-Promoted Ring Openings of N-Tosylaziridines and Epoxides with H2O
  作者：Wen-Long Wei、Xing Li、Bin Ni、Hong-Hong Chang

  DOI：10.3987/com-13-12885

  日期：——

  NaHSO3-oriented ring openings of a wide variety of N-tosylaziridines and epoxides with H2O under mild conditions in acetone was found to be a convenient and effective method, which provided the desired beta-aminoalcohols and beta-diols in good to excellent yields and with uniformly high regioselectivity.