(3S)-4-Phenyl-3-(N-(p-toluenesulfonyl)amino)-2-butanone | 127597-94-8

• 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: (3S)-4-Phenyl-3-(N-(p-toluenesulfonyl)amino)-2-butanone
• 英文别名: (4S)-4-phenyl-3-(tosylamino)butan-2-one；4-phenyl-3-(p-tosylamino)butan-2-one；3-(N-tosyamino)-4-phenyl-2-butanone；4-methyl-N-[(2S)-3-oxo-1-phenylbutan-2-yl]benzenesulfonamide
• CAS: 127597-94-8
• 化学式: C₁₇H₁₉NO₃S
• 分子量: 317.409
• InChiKey: HRVFWKYKVILXJY-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 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：

  (3S)-4-Phenyl-3-(N-(p-toluenesulfonyl)amino)-2-butanone 在 四丁基碘化铵 四氯化钛 、 sodium hydride 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 7.5h， 生成 2-methyl-3-(benzyltosylamino)-4-phenyl-1-butene
  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：

  N-p-tosyl-2-benzylazetidin-3-one 在 碘化钛(IV) 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 生成 4-phenyl-1-(tosylamino)butan-2-one 、 (3S)-4-Phenyl-3-(N-(p-toluenesulfonyl)amino)-2-butanone
  参考文献：
  名称：

  四卤化钛促进2-单取代氮杂环丁烷-3-酮及其O-烷肟的开环反应合成α-氨基酮和O-烷肟

  摘要：

  1.発表论文等（查読付き论文，和书，総说等の発表状况） (1) α-Imino Esters Shimizu的高度非对映选择性串联N-烷基化-曼尼希反应，M.*；栗田，D。Mizota, I. 亚洲人。J.组织。化学。2013, 2, 208-211。(2) 一种新型锂离子电池用聚乙烯醇单离子聚合物电解质 王旭杰；侯YY；高小伟；刘，LL；吴永平*；Shimizu, M. Electrochimica Acta 2013, 87, 113–118。(3) Indolin-3-ones 和 Tetrahydro-4-quinolones 的合成使用 α-Imino Esters Shimizu, M.*; 高尾，Y。桂山，H。Mizota, I. 亚洲人。J.组织。化学。2013 年，第 2 期，第 130-134 页。(4) 四卤化钛促进2-单取代氮杂环丁烷-3-酮及其O-烷肟的开环反应合成α-氨基酮和O-烷肟

  DOI：

  10.3987/com-12-s(n)74

文献信息

• Reductive Aldol and Mannich-Type Reactions of Azetidin-3-ones Promoted by Titanium Tetraiodide
  作者：Shingo Hata、Daisuke Fukuda、Iwao Hachiya、Makoto Shimizu

  DOI：10.1002/asia.200900457

  日期：2010.3.1

  A good promoter: A convenient method is described for the generation and reaction of the enolates of aminoacetone equivalents, which uses the reduction of azetidin‐3‐one with titanium tetraiodide and subsequent reactions with electrophiles. This methodology provides a straightforward access to 1,4‐amino alcohols or diamines in a regioselective manner.

  良好的促进剂：描述了一种方便的方法来生成和反应氨基丙酮当量的烯醇化物，该方法使用四碘化钛还原氮杂环丁烷-3-酮，然后与亲电试剂反应。这种方法可以以区域选择性的方式直接访问1,4-氨基醇或二胺。
• Substituted pyrazoles as p38 kinase inhibitors
  申请人：Naraian S. Ashok

  公开号：US20070078146A1

  公开（公告）日：2007-04-05

  A class of pyrazole derivatives is described for use in treating p38 kinase medicated disorders. Compounds of particular interest are defined by Formula IA wherein R 1 , R 2 , R 3 and R 4 are as described in the specification.

  描述了一类吡唑衍生物，用于治疗p38激酶介导的疾病。特别感兴趣的化合物由公式IA定义，其中R1、R2、R3和R4如规范中所述。
• Allylboration of .alpha.-Amino Ketones
  作者：R. David Pace、George W. Kabalka

  DOI：10.1021/jo00120a029

  日期：1995.7

  A series of unsaturated alpha-amino alcohols were prepared via the allylboration of the corresponding N-protected alpha-amino ketones. The reactions are stereoselective, producing the syn isomers. The diastereoselectivity is not dramatically effected by the electronic nature of the N-protecting group or the reaction temperature but is dependent on the steric requirements of the N-protecting group and the solvent system.
• Substrate-controlled diastereoselectivity in catalyzed and uncatalyzed hydroborations of allylic amine derivatives
  作者：Kevin Burgess、Michael J. Ohlmeyer

  DOI：10.1016/s0040-4039(01)93489-6

  日期：1989.1
• BURGESS, KEVIN;OHLMEYER, MICHAEL J., TETRAHEDRON LETT., 30,(1989) N3, C. 5857-5860
  作者：BURGESS, KEVIN、OHLMEYER, MICHAEL J.

  DOI：——

  日期：——