1-(N-tosylamino)-1-phenyl-2-propanone | 3893-40-1

• 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: 1-(N-tosylamino)-1-phenyl-2-propanone
• 英文别名: N-(2-oxo-1-phenyl-propyl)-4-methyl-benzenosulfonamide；4-methyl-N-(2-oxo-1-phenylpropyl)benzene sulfonamide；α-Tosylamino-α-phenyl-aceton；4-methyl-N-(2-oxo-1-phenylpropyl)benzenesulfonamide
• CAS: 3893-40-1
• 化学式: C₁₆H₁₇NO₃S
• 分子量: 303.382
• InChiKey: ORYZCAPOXRIAJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  1-(N-tosylamino)-1-phenyl-2-propanone 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 三苯基膦 sodium hydroxide 、 乙醇 、 双氧水 、 四氯化钛 、 锌 、 儿萘酚硼烷 作用下， 反应 52.5h， 生成 syn-2-methyl-3-(N-tosylamino)-3-phenyl-1-propanol
  参考文献：
  名称：

  Manipulation of substrate-controlled diastereoselectivities in hydroborations of acyclic allylamine derivatives

  摘要：

  Racemic, and optically active, 2-methyl-3-(N-tosylamino)alkenes I were prepared and subjected to both catalyzed and uncatalyzed hydroborations. Data obtained for the catalyzed hydroborations of these allylamine derivatives are consistent with the theory of secondary orbital interactions in transition metal mediated processes presented in the preceding paper. Surprisingly, diastereoselectivities for conventional (uncatalyzed) hydroborations of the same substrates can be extremely sensitive to the borane used; anti products result when borane-tetrahydrofuran complex is reacted with substrates I (R' = Bn), while with 9-BBN (9-borabicyclo[3.3.1]nonane) these reactions are syn selective. Some of these results are contrary to expectations based upon experimental and theoretical data in the current literature for hydroboration of allylic alcohols. Methodology described in this paper facilitates syntheses of amine alcohols II with extremely high syn and anti selectivities.

  DOI：

  10.1021/jo00003a024
• 作为产物：
  描述：

  tert-butyl N-(phenyl(phenylsulfonyl)methyl)carbamate 在 3-苄基羟乙基甲基噻唑氯化锂 、 碳酸氢钠 、 三乙胺 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 62.0h， 生成 1-(N-tosylamino)-1-phenyl-2-propanone
  参考文献：
  名称：

  不对称转移加氢：α-氨基酮的动态动力学拆分。

  摘要：

  使用不对称转移氢化（ATH）通过动态动力学拆分（DKR）还原了一系列α-氨基酮。使保护基与还原剂匹配，并在优化后对一系列底物进行了研究，从而获得了具有高非对映选择性的产品，在某些情况下具有超过99％ee的产物并实现了完全转化。该方法应用于MDM2-p53抑制剂前体的对映选择性合成。

  DOI：

  10.1021/acs.joc.0c01438

文献信息

• Aldehyde Selective Wacker Oxidations of Phthalimide Protected Allylic Amines: A New Catalytic Route to β³-Amino Acids
  作者：Barbara Weiner、Alejandro Baeza、Thomas Jerphagnon、Ben L. Feringa

  DOI：10.1021/ja902591g

  日期：2009.7.15

  A new method for the synthesis of beta(3)-amino acids is presented. Phthalimide protected allylic amines are oxidized under Wacker conditions selectively to aldehydes using PdCl(2) and CuCl or Pd(MeCN)(2)Cl(NO(2)) and CuCl(2) as complementary catalyst systems. The aldehydes are produced in excellent yields and exhibit a large substrate scope. Beta-amino acids and alcohols are synthesized by oxidation

  提出了一种合成 β(3)-氨基酸的新方法。邻苯二甲酰亚胺保护的烯丙基胺在瓦克条件下选择性地氧化为醛，使用 PdCl(2) 和 CuCl 或 Pd(MeCN)(2)Cl(NO(2)) 和 CuCl(2) 作为补充催化剂系统。醛以极好的收率生产并且表现出大的底物范围。β-氨基酸和醇通过氧化或还原以及随后的脱保护合成。
• A New Zincate-Mediated Rearrangement Reaction of 2-(1-Hydroxyalkyl)-1-alkylcyclopropanol
  作者：Kenichi Nomura、Seijiro Matsubara

  DOI：10.1002/chem.200901054

  日期：2010.1.11

  A novel rearrangement of 2‐(1‐hydroxyalkyl)‐1‐alkylcyclopropanol has been found. It proceeds in the presence of a catalytic amount of organozinc ate complex to give vic‐diols. The rearrangement can be applied to various types of 2‐(1‐hydroxyalkyl)‐1‐alkylcyclopropanol, which can be easily prepared from the corresponding α,β‐epoxyketones and bis(iodozincio)methane. When bicyclo[13.1.0]pentadecane‐1

  发现了2-（1-羟烷基）-1-烷基环丙醇的新颖重排。它在催化量的有机锌络合物存在下进行，得到vic二醇。可以将重排应用于各种类型的2-（1-羟烷基）-1-烷基环丙醇，可以轻松地从相应的α，β-环氧酮和双（碘并甲烷）甲烷制备。用有机锌酸酯络合物处理双环[13.1.0]十五烷-1,15-二醇时，获得了相应的14元环式vic-二醇。因此，该重排对于改变环状基板的环尺寸也是有用的。
• Catalyst-Controlled Wacker-Type Oxidation of Protected Allylic Amines
  作者：Brian W. Michel、Jessica R. McCombs、Andrea Winkler、Matthew S. Sigman

  DOI：10.1002/anie.201004156

  日期：——

  contrary: Utilizing the [Pd(quinox)]–TBHP catalyst system, protected allylic amines were oxidized with high selectivity for the methyl ketone product. This is contrary to the results obtained by the substrate‐controlled Tsuji–Wacker oxidation, which highlights the catalyst‐controlled system presented here (see scheme). A variety of N‐protecting groups undergo selective oxidation with high ketone selectivity

  相反：利用 [Pd(quinox)]-TBHP 催化剂体系，受保护的烯丙胺被氧化，具有高选择性，生成甲基酮产物。这与通过底物控制的 Tsuji-Wacker 氧化获得的结果相反，这突出了此处介绍的催化剂控制系统（参见方案）。各种 N 保护基团以高酮选择性进行选择性氧化。TBHP=叔丁基过氧化氢。
• Inhibitors of Serine Proteases
  申请人：Farmer Luc

  公开号：US20100272681A1

  公开（公告）日：2010-10-28

  The present invention relates to compounds that inhibit serine protease activity, particularly the activity of hepatitis C virus NS3-NS4A protease. As such, they act by interfering with the life cycle of the hepatitis C virus and are also useful as antiviral agents. The invention further relates to compositions comprising these compounds either for ex vivo use or for administration to a patient suffering from HCV infection. The invention also relates to methods of treating an HCV infection in a patient by administering a composition comprising a compound of this invention.

  本发明涉及抑制丝氨酸蛋白酶活性的化合物，特别是针对丙型肝炎病毒NS3-NS4A蛋白酶的活性。这些化合物通过干扰丙型肝炎病毒的生命周期来发挥作用，并且也可用作抗病毒剂。本发明还涉及包含这些化合物的组合物，无论是用于体外使用还是用于治疗患有HCV感染的患者。本发明还涉及通过给患者注射包含本发明化合物的组合物来治疗HCV感染的方法。
• Facile preparation of α-amino ketones from oxidative ring-opening of aziridines by pyridine N-oxide
  作者：Zhi-Bin Luo、Jing-Yu Wu、Xue-Long Hou、Li-Xin Dai

  DOI：10.1039/b711638a

  日期：——

  The oxidative ring-opening reaction of a variety of activated aziridines by pyridine N-oxide provided alpha-amino ketones or alpha-amino aldehydes in good yields.

  各种活化的氮丙啶通过吡啶N-氧化物的氧化开环反应以良好的产率提供了α-氨基酮或α-氨基醛。