4-methyl-N-[(2S)-1-oxopropan-2-yl]-N-prop-2-ynylbenzenesulfonamide | 1232168-45-4

• 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: 4-methyl-N-[(2S)-1-oxopropan-2-yl]-N-prop-2-ynylbenzenesulfonamide
• CAS: 1232168-45-4
• 化学式: C₁₃H₁₅NO₃S
• 分子量: 265.333
• InChiKey: JPBUHSDHWDRUJU-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-methyl-N-[(2S)-1-oxopropan-2-yl]-N-prop-2-ynylbenzenesulfonamide 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.59h， 生成 2-(2-methoxyphenyl)-3,6-dimethyl-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)-N-(1-hydroxypropan-2-yl)-4-methyl-N-(prop-2-yn-1-yl)benzenesulfonamide 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 4-methyl-N-[(2S)-1-oxopropan-2-yl]-N-prop-2-ynylbenzenesulfonamide
  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

• Cp*RuCl‐Vinyl Carbenes: Two Faces and the Bifunctional Role in Catalytic Processes
  作者：Damián Padín、Jesús A. Varela、Carlos Saá

  DOI：10.1002/chem.202000391

  日期：2020.6.10

  Ruthenium vinyl carbenes derived from Cp/Cp*RuCl‐based complexes (Cp=cyclopentadiene, Cp*=1,2,3,4,5‐pentamethylcyclopentadiene) have been routinely invoked as key intermediates in tandem reactions involving a carbene/alkyne metathesis (CAM). A priori, these intermediates resemble the Grubbs‐type family of catalysts, but they exhibit a completely different reactivity pattern that few, if any, other

  在涉及卡宾/炔烃复分解的串联反应中，通常将Cp / Cp * RuCl基络合物（Cp =环戊二烯，Cp * = 1,2,3,4,5-戊甲基环戊二烯）衍生的钌乙烯基卡宾烯作为关键中间体（ CAM）。先验地，这些中间体类似于Grubbs型催化剂家族，但是它们展现出完全不同的反应模式，到目前为止，几乎没有其他催化系统可以复制。这些物质与α-未取代的和α-取代的炔基的反应性证明了这些中间体的特殊性。尽管Z-乙烯基二氢恶嗪优先从前者获得，但Z-乙烯基环氧吡咯烷是由后者获得。光谱和计算数据的组合现在证明一个η 3钌乙烯基卡宾的配位模式和路易斯碱性氯化物配体的存在会产生两个明显不同的立体电子面，这是这些物质非常规反应的原因。
• Diastereoselective Syntheses of Functionalized Five-Membered Carbocycles and Heterocycles by a SmI₂-Promoted Intramolecular Coupling of Bromoalkynes and α,β-Unsaturated Esters
  作者：Kazunori Takahashi、Toshio Honda

  DOI：10.1021/ol101034s

  日期：2010.7.2

  An intramolecular coupling of bromoalkynes with alpha,beta-unsaturated esters afforded functionalized five-membered carbocycles and heterocycles with high diastereoselectivities in excellent yields. The vinyl bromides newly generated as the products serve as adequate intermediates for further chemical modification.