6a-methyl-3-methylene-5-(toluene-4-sulfonyl)hexahydrofuro[2,3-c]pyrrol-2-one

• 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: 6a-methyl-3-methylene-5-(toluene-4-sulfonyl)hexahydrofuro[2,3-c]pyrrol-2-one
• 英文别名: (3aRS,6aRS)-6a-methyl-3-methylene-5-tosylhexahydro-2H-furo[2,3-c]pyrrol-2-one；(3aS,6aS)-6a-methyl-3-methylidene-5-(4-methylphenyl)sulfonyl-4,6-dihydro-3aH-furo[2,3-c]pyrrol-2-one
• 化学式: C₁₅H₁₇NO₄S
• 分子量: 307.37
• InChiKey: KREYYGFBZBLJIX-UKRRQHHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-methyl-1-(toluene-4-sulfonyl)-4-(1-triethylsilanylvinyl)pyrrolidin-3-ol 在 溴 、 双三苯基膦二羰基镍 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.67h， 生成 6a-methyl-3-methylene-5-(toluene-4-sulfonyl)hexahydrofuro[2,3-c]pyrrol-2-one
  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

• Synthesis of<i>α</i>-Methylene-<i>γ</i>-butyrolactones: Ru-Catalyzed Cyclocarbonylation of Allenyl Aldehydes and Allenyl Ketones
  作者：Suk-Ku Kang、Kwang-Jin Kim、Young-Taek Hong

  DOI：10.1002/1521-3773(20020503)41:9<1584::aid-anie1584>3.0.co;2-y

  日期：2002.5.3
• 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.