(1R,2R)-2-methyl-3-oxocyclopentanecarbaldehyde

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2R)-2-methyl-3-oxocyclopentanecarbaldehyde
• 英文别名: (1R,2R)-2-methyl-3-oxocyclopentane-1-carbaldehyde
• 化学式: C₇H₁₀O₂
• 分子量: 126.155
• InChiKey: PORSLRXAINXJMJ-RITPCOANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  甲基环戊烯醇酮 在 2,3-二巯基丁二酸 、 四丁基氟化铵 、 臭氧 作用下， 以 四氢呋喃 为溶剂， 生成 (1R,2R)-2-methyl-3-oxocyclopentanecarbaldehyde
  参考文献：
  名称：

  Enantioselective Nucleophilic Formylation and Cyanation of Conjugated Enones via Michael Addition of Formaldehyde SAMP-Hydrazone

  摘要：

  DOI：

  10.1021/ja9610500

文献信息

• Formaldehyde Dialkylhydrazones as Neutral Formyl Anion and Cyanide Equivalents:  Nucleophilic Addition to Conjugated Enones
  作者：Elena Díez、Rosario Fernández、Consolación Gasch、José M. Lassaletta、José M. Llera、Eloísa Martín-Zamora、Juan Vázquez

  DOI：10.1021/jo970481d

  日期：1997.7.1

  A versatile methodology for the nucleophilic formylation and cyanation of conjugated enones is reported. The procedure is based on the use of formaldehyde dimethylhydrazone, which, acting as a neutral formyl anion equivalent, adds to preformed trialkylsilyl-enone complexes. Both 4-(silyloxy)-3-enal hydrazones 3 or deprotected 4-oxo aldehyde monohydrazones 4 can be obtained as products depending on quenching conditions. In full analogy, an asymmetric version of the reaction using chiral formaldehyde SAMP-hydrazone as a neutral synthon of the chiral formyl anion has been developed, giving rise to the corresponding adducts 5 and 6 in good yields and with excellent diastereoselectivities (de 85-greater than or equal to 98%). Ozonolysis or HCl-mediated hydrolysis of adducts 4 and 6 readily affords racemic and optically enriched 4-oxo aldehydes 7, respectively. Additionally, high-yielding MMPP-oxidative cleavage of 4-oxo hydrazones 4 and 6 has been performed to obtain Li-oxo nitriles 8 in racemic and optically enriched forms, respectively. In this way, interesting chiral bifunctional building blocks, some of them bearing newly created stereogenic quaternary centers, have been efficiently synthesized.
• Enantioselective Nucleophilic Formylation and Cyanation of Conjugated Enones <i>via</i> Michael Addition of Formaldehyde SAMP-Hydrazone
  作者：Jose-María Lassaletta、Rosario Fernández、Eloísa Martín-Zamora、Elena Díez

  DOI：10.1021/ja9610500

  日期：1996.1.1