N-buta-2,3-dienyl-4-methyl-N-(2-oxobutyl)benzenesulfonamide

• 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: N-buta-2,3-dienyl-4-methyl-N-(2-oxobutyl)benzenesulfonamide
• 化学式: C₁₅H₁₉NO₃S
• 分子量: 293.387
• InChiKey: UQZIXMBTYLTQGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  三乙基硅烷 、 N-buta-2,3-dienyl-4-methyl-N-(2-oxobutyl)benzenesulfonamide 在 acetylacetonatodicarbonylrhodium(l) 、 一氧化碳 作用下， 以 乙醚 为溶剂， 70.0 ℃ 、1.01 MPa 条件下， 以56%的产率得到3-ethyl-1-(toluene-4-sulfonyl)-4-(1-triethylsilanylvinyl)pyrrolidin-3-ol
  参考文献：
  名称：

  Silylative Carbocyclization of Allenyl-carbonyl Units with Et₃SiH Catalyzed by Rhodium:  Cis-Stereoselective Synthesis of Homoallylic Cycloalkanols

  摘要：

  GraphicsA new procedure for the synthesis of cis-2-triethylsilylvinyl-cyclopentanois and -cyclohexanols from allenyl-aldehydes and -ketones with Et-3-SiH through rhodium-catalyzed silylative carbocyclization is described. The use of Rh(acac)(CO)(2) (1 mol %) to promote the reaction results in a mild and convenient protocol for the three-component assembly.

  DOI：

  10.1021/ol034787k

文献信息

• cis-Stereoselective nickel-catalyzed cyclization/alkylation and arylation reactions of allenyl-aldehydes and -ketones with organozinc reagentsElectronic supplementary information (ESI) available: typical procedures, NMR-data, and X-ray data. See http://www.rsc.org/suppdata/cc/b2/b207620a/
  作者：Suk-Ku Kang、Seok-Keun Yoon

  DOI：10.1039/b207620a

  日期：2002.11.4

  Highly stereoselective alkylative and arylative cyclization reactions of allenyl-aldehydes and -ketones with organozinc reagents occur efficiently in the presence of catalytic Ni(COD)2 to afford cis-fused homoallylic cyclopentanols.

  在催化Ni（COD）2的存在下，烯丙基-醛和-酮与有机锌试剂的高度立体选择性烷基化和芳基化环化反应可有效发生，以提供顺式稠合均烯丙基环戊醇。
• A Convenient Synthesis of α-Methylene-γ-butyrolactones from Allenyl Carbonyl Units Mediated by Mo(CO)₆ through Intramolecular Cyclocarbonylation
  作者：Chan-Mo Yu、Young-Taek Hong、Joon-Hwan Lee

  DOI：10.1021/jo049252z

  日期：2004.11.1

  A novel procedure for the synthesis of cis-fused bicyclic alpha-methylene-gamma-butyrolactones from allenyl carbonyl functionalities via the molybdenum-mediated cyclocarbonylation is described. The use Of MO(CO)(6) with DMSO to promote reaction results in an efficient and convenient protocol through the three-component assembly in high yields.
• Silylative Carbocyclization of Allenyl-carbonyl Units with Et₃SiH Catalyzed by Rhodium:  Cis-Stereoselective Synthesis of Homoallylic Cycloalkanols
  作者：Suk-Ku Kang、Young-Taek Hong、Joon-Hwan Lee、Won-Yeol Kim、Inhee Lee、Chan-Mo Yu

  DOI：10.1021/ol034787k

  日期：2003.8.1

  GraphicsA new procedure for the synthesis of cis-2-triethylsilylvinyl-cyclopentanois and -cyclohexanols from allenyl-aldehydes and -ketones with Et-3-SiH through rhodium-catalyzed silylative carbocyclization is described. The use of Rh(acac)(CO)(2) (1 mol %) to promote the reaction results in a mild and convenient protocol for the three-component assembly.