Benzyl-((S)-1-methyl-4-oxo-pentyl)-carbamic acid tert-butyl ester | 445432-15-5

• 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: Benzyl-((S)-1-methyl-4-oxo-pentyl)-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-benzyl-N-[(2S)-5-oxohexan-2-yl]carbamate
• CAS: 445432-15-5
• 化学式: C₁₈H₂₇NO₃
• 分子量: 305.417
• InChiKey: FVFJGCXKNANTFD-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Benzyl-((S)-1-methyl-4-oxo-pentyl)-carbamic acid tert-butyl ester 、 三甲基硅烷化重氮甲烷 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 Benzyl-((S)-1,3-dimethyl-cyclopent-2-enyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Scope and limitations of the alkylidene carbene 1,5-CH insertion reactions of α-amino acid-derived substrates

  摘要：

  A range of alpha-amino acid-derived cyclisation precursors were synthesised from suitably protected alpha-amino esters, via a Dibal-H/Wittig/catalytic hydrogenation strategy and each of these was subjected to alkylidene carbene-forming conditions (lithio(trimethylsilyl)diazomethane, THF). The cyclisations proceeded in poor to good yield, with the best cyclisations occurring to produce spirocyclic products. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(02)00585-3
• 作为产物：
  描述：

  N-benzyl-N-Boc-L-alaninal 在 palladium on activated charcoal 氢气 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 Benzyl-((S)-1-methyl-4-oxo-pentyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Scope and limitations of the alkylidene carbene 1,5-CH insertion reactions of α-amino acid-derived substrates

  摘要：

  A range of alpha-amino acid-derived cyclisation precursors were synthesised from suitably protected alpha-amino esters, via a Dibal-H/Wittig/catalytic hydrogenation strategy and each of these was subjected to alkylidene carbene-forming conditions (lithio(trimethylsilyl)diazomethane, THF). The cyclisations proceeded in poor to good yield, with the best cyclisations occurring to produce spirocyclic products. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(02)00585-3

文献信息

• Metal-Free, Mild, Nonepimerizing, Chemo- and Enantio- or Diastereoselective N-Alkylation of Amines by Alcohols via Oxidation/Imine–Iminium Formation/Reductive Amination: A Pragmatic Synthesis of Octahydropyrazinopyridoindoles and Higher Ring Analogues
  作者：Imran A. Khan、Anil K. Saxena

  DOI：10.1021/jo4012249

  日期：2013.12.6

  A mild step and atom-economical nonepimerizing chemo- and enantioselective N-alkylating procedure has been developed via oxidation/imine–iminium formation/reduction cascade using TEMPO–BAIB–HEH–Brønsted acid catalysis in DMPU as solvent and a stoichiometric amount of amine. The optimized conditions were further extended for the nonenzymatic kinetic resolution of the chiral amine thus formed under nonenzymatic

  通过在DMPU中使用TEMPO-BAIB-HEH-Brønsted酸催化作为溶剂和化学计量的胺，通过氧化/亚胺-亚胺形成/还原级联反应，开发了一种温和的步骤以及原子经济的非三聚化学和对映选择性N-烷基化方法。优化的条件进一步扩展为使用VAPOL衍生的磷酸（VAPOL-PA）作为布朗斯台德酸催化剂在非酶原位氢转移条件下形成的手性胺的非酶动力学拆分。所呈现的反应的对映选择性级联被成功地用于在octahydropyrazinopyridoindole的合成和其较高的环类似物。
• Scope and limitations of the alkylidene carbene 1,5-CH insertion reactions of α-amino acid-derived substrates
  作者：Renameditswe Mapitse、Christopher J Hayes

  DOI：10.1016/s0040-4039(02)00585-3

  日期：2002.5

  A range of alpha-amino acid-derived cyclisation precursors were synthesised from suitably protected alpha-amino esters, via a Dibal-H/Wittig/catalytic hydrogenation strategy and each of these was subjected to alkylidene carbene-forming conditions (lithio(trimethylsilyl)diazomethane, THF). The cyclisations proceeded in poor to good yield, with the best cyclisations occurring to produce spirocyclic products. (C) 2002 Published by Elsevier Science Ltd.