(3aRS,6aRS)-3-methylene-5-(p-toluenesulfonyl)-hexahydro-2H-furo[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: (3aRS,6aRS)-3-methylene-5-(p-toluenesulfonyl)-hexahydro-2H-furo[2,3-c]pyrrol-2-one
• 英文别名: 3-methylene-5-(toluene-4-sulfonyl)hexahydrofuro[2,3-c]pyrrol-2-one；(3aRS,6aRS)-3-methylene-5-tosylhexahydro-2H-furo[2,3-c]pyrrol-2-one；(3aS,6aS)-3-methylidene-5-(4-methylphenyl)sulfonyl-3a,4,6,6a-tetrahydrofuro[2,3-c]pyrrol-2-one
• 化学式: C₁₄H₁₅NO₄S
• 分子量: 293.343
• InChiKey: YZWOZRQQVFGQBS-CHWSQXEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3aRS,6aRS)-3-methylene-5-(p-toluenesulfonyl)-hexahydro-2H-furo[2,3-c]pyrrol-2-one 在 六甲基磷酰三胺 、 copper(l) iodide 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以67%的产率得到(3RS,3aSR,6aSR)-3-methyl-5-tosylhexahydro-2H-furo[2,3-c]pyrrol-2-one
  参考文献：
  名称：

  A Convenient Synthesis of α-Methylene-γ-butyrolactones from Allenyl Carbonyl Units Mediated by Mo(CO)₆ through Intramolecular Cyclocarbonylation

  摘要：

  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.

  DOI：

  10.1021/jo049252z
• 作为产物：
  描述：

  4-甲基-N-(丙-2-炔-1-基)苯-1-磺酰胺 在 十二羰基三钌 、 potassium carbonate 、 二异丙胺 、 三氟乙酸 、 copper(I) bromide 作用下， 以 1,4-二氧六环 、 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 120.0 ℃ 、2.03 MPa 条件下， 反应 23.5h， 生成 (3aRS,6aRS)-3-methylene-5-(p-toluenesulfonyl)-hexahydro-2H-furo[2,3-c]pyrrol-2-one
  参考文献：
  名称：

  α-亚甲基-γ-丁内酯的合成：Ru催化的烯基醛和烯基酮的环羰基化。

  摘要：

  DOI：

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

文献信息

• 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.
• Regulation of Stereoselectivity Using Lewis Acid in the Cyclization of Allenic Aldehydes Catalyzed by Palladium Complex
  作者：Chan-Mo Yu、Jinsuop Youn、Min-Kyoung Lee

  DOI：10.1021/ol0513701

  日期：2005.8.1

  [GRAPHICS]A highly diastereoselective synthesis of 3 is achieved from the reaction of 1 with hexamethylditin catalyzed by palladium complex in the presence of 20 mol % tris(pentafluorophenyl)borane as a Lewis acid additive for a reversal of diastereoselectivity, whereas 2 is formed in the absence of Lewis acid additive. The method described herein is successful with various substrates 1 in good yields and high levels of diastereoselectivity.
• 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.