(3S,R_S)-N-(tert-butoxycarbonyl)-3-amino-5-methyl-1-[(4-methylphenyl)sulfinyl]-2-hexanone | 472999-82-9

• 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-5-methyl-1-[(4-methylphenyl)sulfinyl]-2-hexanone
• 英文别名: (3S,R(S))-N-(tert-butoxycarbonyl)-3-amino-5-methyl-1-(p-tolylsulfinyl)-2-hexanone；tert-butyl N-[(3S)-5-methyl-1-[(R)-(4-methylphenyl)sulfinyl]-2-oxohexan-3-yl]carbamate
• CAS: 472999-82-9
• 化学式: C₁₉H₂₉NO₄S
• 分子量: 367.51
• InChiKey: ZTDHZNSFQWXAEO-IVCQMTBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 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-5-methyl-1-[(4-methylphenyl)sulfinyl]-2-hexanone 在 盐酸 、 titanium(III) chloride 、 trimethoxonium tetrafluoroborate 、 zinc dibromide 作用下， 以 四氢呋喃 、 乙醇 、 Petroleum ether 为溶剂， 反应 27.83h， 生成 (R)-1-[(S)-1-(tert-butoxycarbonylamino)-3-methylbutyl]oxirane
  参考文献：
  名称：

  A stereodivergent approach to syn- and anti-β-hydroxy-γ-amino acids. Enantioselective synthesis of N-Boc-statine and N-Boc-3-epistatine mediated by sulfoxides

  摘要：

  Asymmetric syntheses of the syn- and anti-stereoisomers of N-Boc statine, based on the stereodivergent reduction of a single sulfoxide 5, derived from N-Boc-L-leucine, are reported. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00819-4
• 作为产物：
  描述：

  (R)-(+)-甲基对甲苯砜 、 BOC-L-亮氨酸甲酯 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 以89%的产率得到(3S,R_S)-N-(tert-butoxycarbonyl)-3-amino-5-methyl-1-[(4-methylphenyl)sulfinyl]-2-hexanone
  参考文献：
  名称：

  γ-Amino vinyl sulfoxides in asymmetric synthesis. Synthesis of optically pure α-substituted β-amino nitriles

  摘要：

  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.

  DOI：

  10.1016/j.tet.2008.10.037

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.
• A stereodivergent approach to syn- and anti-β-hydroxy-γ-amino acids. Enantioselective synthesis of N-Boc-statine and N-Boc-3-epistatine mediated by sulfoxides
  作者：Francisco Yuste、Angel Dı́az、Benjamı́n Ortiz、Rubén Sánchez-Obregón、Fernando Walls、José L.Garcı́a Ruano

  DOI：10.1016/s0957-4166(02)00819-4

  日期：2003.3

  Asymmetric syntheses of the syn- and anti-stereoisomers of N-Boc statine, based on the stereodivergent reduction of a single sulfoxide 5, derived from N-Boc-L-leucine, are reported. (C) 2003 Elsevier Science Ltd. All rights reserved.