(R)-2-methyl-N-((R)-1-phenylpent-4-en-1-yl)propane-2-sulfinamide | 943231-77-4

• 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: (R)-2-methyl-N-((R)-1-phenylpent-4-en-1-yl)propane-2-sulfinamide
• 英文别名: N-(tert-butanesulfinyl)-1-phenylpent-4-en-1-amine
• CAS: 943231-77-4
• 化学式: C₁₅H₂₃NOS
• 分子量: 265.42
• InChiKey: DYDMUEXVSWUNRY-RDTXWAMCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  18.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  29.1
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (R)-2-methyl-N-((R)-1-phenylpent-4-en-1-yl)propane-2-sulfinamide 在 盐酸 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 0.83h， 生成 (R)-(+)-N-Benzyloxycarbonyl-1-phenylpent-4-enylamine
  参考文献：
  名称：

  Microwave-Assisted Tandem Cross Metathesis Intramolecular Aza-Michael Reaction:  An Easy Entry to Cyclic β-Amino Carbonyl Derivatives

  摘要：

  Hoveyda-Grubbs catalyst in combination with BF3 center dot OEt2 efficiently promotes tandem cross metathesis intramolecular aza-Michael reaction between enones and unsaturated carbamates resulting in the creation of beta-amino carbonyl units. The use of microwave irradiation dramatically accelerates the process, enhancing the synthetic utility of this methodology for the preparation of these types of derivatives. When enantiomerically enriched alpha-branched amines were used as starting materials, the process was also very efficient, although with modest selectivity in the newly created stereocenter. The use of microwave irradiation led to an interesting effect, inverting the selectivity in the addition process.

  DOI：

  10.1021/ja0709829
• 作为产物：
  描述：

  4-戊烯醛 在 titanium(IV) tetraethanolate 作用下， 以 二氯甲烷 为溶剂， 反应 21.5h， 生成 (R)-2-methyl-N-((R)-1-phenylpent-4-en-1-yl)propane-2-sulfinamide
  参考文献：
  名称：

  Microwave-Assisted Tandem Cross Metathesis Intramolecular Aza-Michael Reaction:  An Easy Entry to Cyclic β-Amino Carbonyl Derivatives

  摘要：

  Hoveyda-Grubbs catalyst in combination with BF3 center dot OEt2 efficiently promotes tandem cross metathesis intramolecular aza-Michael reaction between enones and unsaturated carbamates resulting in the creation of beta-amino carbonyl units. The use of microwave irradiation dramatically accelerates the process, enhancing the synthetic utility of this methodology for the preparation of these types of derivatives. When enantiomerically enriched alpha-branched amines were used as starting materials, the process was also very efficient, although with modest selectivity in the newly created stereocenter. The use of microwave irradiation led to an interesting effect, inverting the selectivity in the addition process.

  DOI：

  10.1021/ja0709829

文献信息

• Oxidation of Primary Alcohols and Aldehydes to Carboxylic Acids via Hydrogen Atom Transfer
  作者：Wen-Yun Tan、Yi Lu、Jing-Feng Zhao、Wen Chen、Hongbin Zhang

  DOI：10.1021/acs.orglett.1c02188

  日期：2021.9.3

  The oxidation of primary alcohols and aldehydes to the corresponding carboxylic acids is a fundamental reaction in organic synthesis. In this paper, we report a new chemoselective process for the oxidation of primary alcohols and aldehydes. This metal-free reaction features a new oxidant, an easy to handle procedure, high isolated yields, and good to excellent functional group tolerance even in the

  伯醇和伯醛氧化成相应的羧酸是有机合成中的基本反应。在本文中，我们报告了一种用于氧化伯醇和醛的新化学选择性工艺。这种无金属反应具有新的氧化剂、易于操作的程序、高分离产率以及即使在易受攻击的仲醇和叔丁烷亚磺酰胺存在下也具有良好至优异的官能团耐受性的特点。
• Diastereoselective Homoallylation and bis-homoallylation of N-tertbutanesulfinyl Imines with Organomagnesium Compounds
  作者：Ana Sirvent、Francisco Foubelo

  DOI：10.2174/1570178614666171130162244

  日期：2018.4.12

  The addition of but-3-enylmagnesium bromide and pent-4-enylmagnesium bromide to N-tert-butanesulfinyl aldimines in toluene as solvent proceeds with high diastereoselectivity to yield the corresponding products of homoallylation and bis-homoallylation, respectively. The reactions are diastereoselective, and the configuration of the sulfur atom of the sulfinyl group determined the stereochemical outcome. The reaction products are aminoalkene derivatives of potential synthetic interest as precursors of nitrogen containing heterocycles.

  在甲苯溶剂中，丁-3-烯基溴化镁和戊-4-烯基溴化镁与 N-叔丁基亚磺酰亚胺的加成反应具有很高的非对映选择性，可分别生成相应的均烯丙基化产物和双均烯丙基化产物。反应具有非对映选择性，而亚磺酰基硫原子的构型决定了立体化学结果。反应产物是具有潜在合成兴趣的氨基烯衍生物，可作为含氮杂环的前体。
• N-Sulfinyl Amines as a Nitrogen Source in the Asymmetric Intramolecular Aza-Michael Reaction: Total Synthesis of (−)-Pinidinol
  作者：Santos Fustero、Silvia Monteagudo、María Sánchez-Roselló、Sonia Flores、Pablo Barrio、Carlos del Pozo

  DOI：10.1002/chem.201000615

  日期：2010.8.23

  N‐Sulfinyl amines have been successfully employed as nitrogen nucleophiles for the asymmetric intramolecular aza‐Michael reaction. The synthetic strategy involves a cross‐metathesis reaction followed by the Michael‐type cyclization, either in a base‐catalyzed two‐step procedure or in a tandem fashion. The developed methodology allows access to chiral substituted pyrrolidines and piperidines bearing

  N-亚磺胺已被成功地用作不对称分子内氮杂-Michael反应的氮亲核试剂。合成策略涉及交叉易位反应，然后进行迈克尔型环化反应，可采用碱催化的两步法或串联方式进行。发达的方法学允许访问带有一个或两个立体中心的手性取代的吡咯烷和哌啶，并且该方法已用于哌啶生物碱（-）-哌啶子醇的合成。