(S)-N-(1-hydroxy-4-methylpentan-2-yl)-4-methyl-N-(prop-2-yn-1-yl)benzenesulfonamide | 1378523-76-2

• 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: (S)-N-(1-hydroxy-4-methylpentan-2-yl)-4-methyl-N-(prop-2-yn-1-yl)benzenesulfonamide
• 英文别名: N-(1-(hydroxymethyl)-3-methylbutyl)-4-methyl-N-prop-2-ynyl-benzenesulfonamide；N-[(2S)-1-hydroxy-4-methylpentan-2-yl]-4-methyl-N-prop-2-ynylbenzenesulfonamide
• CAS: 1378523-76-2
• 化学式: C₁₆H₂₃NO₃S
• 分子量: 309.43
• InChiKey: BFLYZDRDGAESGH-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 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：
  66
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-N-(1-hydroxy-4-methylpentan-2-yl)-4-methyl-N-(prop-2-yn-1-yl)benzenesulfonamide 在 sodium hydride 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.59h， 生成 3-isobutyl-2-(3-methoxyphenyl)-6-methyl-4-(toluene-4-sulfonyl)-3,4-dihydro-2H-[1,4]oxazine
  参考文献：
  名称：

  A New Approach to 1,4-Oxazines and 1,4-Oxazepines via Base-Promoted Exo Mode Cyclization of Alkynyl Alcohols: Mechanism and DFT Studies

  摘要：

  A new approach was developed to synthesize 1,4-oxazine and 1,4-oxazepine derivatives without solvent and metal. Regioselective cyclization occurred to afford exclusively the exo-clig product, and stereochemistry was studied by circular dichroism and specific optical rotation techniques. The Grignard reaction is a key synthetic step to produce high diastereomeric compounds via Cram's rule and was well supported by DFT calculations. A hydroalkoxylation mechanism was proposed and supported by DFT calculations.

  DOI：

  10.1021/ol301219c
• 作为产物：
  描述：

  (S)-4-methyl-2-(toluene-4-sulfonamido)pentanoic acid 在 锂硼氢 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 乙腈 为溶剂， 反应 5.0h， 生成 (S)-N-(1-hydroxy-4-methylpentan-2-yl)-4-methyl-N-(prop-2-yn-1-yl)benzenesulfonamide
  参考文献：
  名称：

  A New Approach to 1,4-Oxazines and 1,4-Oxazepines via Base-Promoted Exo Mode Cyclization of Alkynyl Alcohols: Mechanism and DFT Studies

  摘要：

  A new approach was developed to synthesize 1,4-oxazine and 1,4-oxazepine derivatives without solvent and metal. Regioselective cyclization occurred to afford exclusively the exo-clig product, and stereochemistry was studied by circular dichroism and specific optical rotation techniques. The Grignard reaction is a key synthetic step to produce high diastereomeric compounds via Cram's rule and was well supported by DFT calculations. A hydroalkoxylation mechanism was proposed and supported by DFT calculations.

  DOI：

  10.1021/ol301219c

文献信息

• Highly exo selective, photochemically promoted cyclization of iodoallene derivatives
  作者：Milos Jovanovic、Milena Simic、Milos Petkovic、Gordana Tasic、Veselin Maslak、Predrag Jovanovic、Vladimir Savic

  DOI：10.1002/jhet.4472

  日期：2022.8

  A photochemically promoted intramolecular cyclization of aryl-, vinyl-, and alkyliodo allenes has been developed. The optimal conditions employed [Ir(ppy)2(dtbbpy)]PF6 (1 mol%) as catalyst affording products with high exo selectivity in moderate to good yields. Chiral substrates showed diastereoselectivity of up to 95/5 favoring trans product.

  已经开发了一种光化学促进的芳基、乙烯基和烷基碘丙二烯的分子内环化。最佳条件采用 [Ir(ppy) 2 (dtbbpy)]PF 6 (1 mol%) 作为催化剂，以中等至良好的收率提供具有高 exo 选择性的产物。手性底物显示高达 95/5 的非对映选择性，有利于反式产物。
• Rhodium-catalyzed diastereoselective synthesis of highly substituted morpholines from nitrogen-tethered allenols
  作者：A. Ziyaei Halimehjani、B. Breit

  DOI：10.1039/d3cc00151b

  日期：——

  Rhodium-catalyzed intramolecular cyclization of nitrogen-tethered allenols was investigated for the synthesis of functionalized morpholines. By using this strategy, various N-protected 2,5- and 2,6-disubstituted as well as 2,3,5- and 2,5,6-trisubstituted morpholines were obtained via an atom-economic pathway with high to excellent yields, diastereo- and enantioselectivities (up to 99% yield, up to

  研究了铑催化的氮拴联烯醇的分子内环化以合成功能化的吗啉。通过使用该策略，通过原子经济途径获得了各种N保护的 2,5- 和 2,6- 二取代以及 2,3,5- 和 2,5,6- 三取代吗啉，收率高至极佳、非对映选择性和对映选择性（产率高达 99%，高达 >99 : 1 dr 和高达 >99.9 ee）。还研究了合成吗啉在臭氧分解、水合、复分解和环氧化反应中的效用。
• Deciphering substitution effects on reductive hydroalkoxylation of alkynyl aminols for stereoselective synthesis of morpholines and 1,4-oxazepanes: total synthesis of tridemorph and fenpropimorph
  作者：Santosh J. Gharpure、Deepika Kalita、Shipra Somani、Juhi Pal

  DOI：10.1039/d4ob00855c

  日期：——

  Acid catalysed reductive etherification of N-propargyl amino alcohols for the stereoselective synthesis of cis-2,5/2,6-disubstituted morpholines and cis-2,6/2,7-disubstituted oxazepanes has been developed. Mechanistic studies revealed that terminal alkynols gave morpholines via a 6-exo-dig hydroalkoxylation–isomerization–reduction cascade. Interestingly, an alkyne hydration–cyclization–reduction sequence

  开发了用于立体选择性合成顺式-2,5/2,6-二取代吗啉和顺式-2,6/2,7-二取代氧氮杂环庚烷的N-炔丙基氨基醇的酸催化还原醚化反应。机理研究表明，末端炔醇通过6- exo-dig加氢烷氧基化-异构化-还原级联产生吗啉。有趣的是，发现炔烃水合-环化-还原序列参与由烷基取代的内部炔醇形成氧氮杂环庚烷。该策略被用作杀菌剂十三吗啉和丁苯吗啉全合成的关键步骤。
• Synthesis of Amino Acid derived 2-Methylene Morpholines and 3,4-dihydro-2H-1,4-Oxazines via Ag (I) promoted Intra-molecular Cyclization of Alkynols
  作者：Amit Kumar、Sandeep Bhattacherjee、Gautam Panda

  DOI：10.24820/ark.5550190.p011.871

  日期：——