(3S,R_S)-N-(tert-butoxycarbonyl)-3-amino-1-(p-tolylsulfinyl)-2-butanone | 310450-35-2

• 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,R_S)-N-(tert-butoxycarbonyl)-3-amino-1-(p-tolylsulfinyl)-2-butanone
• 英文别名: tert-butyl N-[(2S)-4-[(R)-(4-methylphenyl)sulfinyl]-3-oxobutan-2-yl]carbamate
• CAS: 310450-35-2
• 化学式: C₁₆H₂₃NO₄S
• 分子量: 325.429
• InChiKey: BYMIPJOKRVHCQX-AMXDTQDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  91.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S,R_S)-N-(tert-butoxycarbonyl)-3-amino-1-(p-tolylsulfinyl)-2-butanone 在 镍 、 二异丁基氢化铝 、 zinc dibromide 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 2.0h， 生成 2-甲基-2-丙基[(2S,3S)-3-羟基-2-丁烷基]氨基甲酸酯
  参考文献：
  名称：

  Synthesis of enantiomerically pure 2-amino alcohols from amino acids mediated by sulfoxides

  摘要：

  Enantiomerically pure (R-1,S-2)- and (S-1,S-2)-2-amino alcohols can be easily synthesized by stereodivergent reduction of alpha'-(N-Boc)amino beta-keto sulfoxides (easily synthesized from readily available N-Boc amino eater hydrochlorides) with DIBAH (clr 82-92%) and DIBAH/ZnBr2 (de 80%), followed by hydrogenolysis of the C-S bond of the resulting hydroxy sulfoxides and final hydrolysis of the N-Boc protecting group. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00264-0
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 29.0h， 生成 (3S,R_S)-N-(tert-butoxycarbonyl)-3-amino-1-(p-tolylsulfinyl)-2-butanone
  参考文献：
  名称：

  Synthesis of enantiomerically pure 2-amino alcohols from amino acids mediated by sulfoxides

  摘要：

  Enantiomerically pure (R-1,S-2)- and (S-1,S-2)-2-amino alcohols can be easily synthesized by stereodivergent reduction of alpha'-(N-Boc)amino beta-keto sulfoxides (easily synthesized from readily available N-Boc amino eater hydrochlorides) with DIBAH (clr 82-92%) and DIBAH/ZnBr2 (de 80%), followed by hydrogenolysis of the C-S bond of the resulting hydroxy sulfoxides and final hydrolysis of the N-Boc protecting group. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00264-0

文献信息

• γ-Amino vinyl sulfoxides in asymmetric synthesis. Synthesis of optically pure α-substituted β-amino nitriles
  作者：Ricardo Alfaro、Francisco Yuste、Benjamín Ortiz、Rubén Sánchez-Obregón、José L. García Ruano

  DOI：10.1016/j.tet.2008.10.037

  日期：2009.1

  The synthesis of optically pure (E)- and (Z)-gamma-amino vinyl sulfoxides derived from commercially available protected alpha-amino esters is reported. Hydrocyanation of the double bond with Et2AlCN is completely stereoselective and provides enantiomerically pure alpha-substituted beta-amino nitriles with complete control of the configuration at the alpha-carbon being exerted by the sulfinyl group. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis of enantiomerically pure 2-amino alcohols from amino acids mediated by sulfoxides
  作者：Francisco Yuste、Benjamin Ortiz、Alejandra Carrasco、Martha Peralta、Leticia Quintero、Rubén Sánchez-Obregón、Fernando Walls、José L Garcı́a Ruano

  DOI：10.1016/s0957-4166(00)00264-0

  日期：2000.8

  Enantiomerically pure (R-1,S-2)- and (S-1,S-2)-2-amino alcohols can be easily synthesized by stereodivergent reduction of alpha'-(N-Boc)amino beta-keto sulfoxides (easily synthesized from readily available N-Boc amino eater hydrochlorides) with DIBAH (clr 82-92%) and DIBAH/ZnBr2 (de 80%), followed by hydrogenolysis of the C-S bond of the resulting hydroxy sulfoxides and final hydrolysis of the N-Boc protecting group. (C) 2000 Elsevier Science Ltd. All rights reserved.