(2R,3S,4R,5R)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(furan-3-yl)-2-methyl-4-nitrocyclohexan-1-one | 194807-38-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (2R,3S,4R,5R)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(furan-3-yl)-2-methyl-4-nitrocyclohexan-1-one
• CAS: 194807-38-0
• 化学式: C₁₈H₂₉NO₅Si
• 分子量: 367.517
• InChiKey: OOGZCLWYKSYHHZ-JJAZEVLHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.26
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  85.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R,5R)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(furan-3-yl)-2-methyl-4-nitrocyclohexan-1-one 在 镍 ruthenium trichloride 、 sodium periodate 、 氢气 作用下， 以 四氯化碳 、 乙醚 、 乙醇 、 水 、 乙腈 为溶剂， 60.0 ℃ 、9.12 MPa 条件下， 反应 6.5h， 生成 (+)-methyl (1S,2S,3S,4R)-3-(tert-butyldimethylsilyloxymethyl)-2-amino-4-methyl-5-oxocyclohexane-1-carboxylate
  参考文献：
  名称：

  Synthesis of Enantiomerically Pure Functionalized cis- and trans-2-Aminocyclohexanecarboxylic Acid Derivatives

  摘要：

  DOI：

  10.1021/jo981511v
• 作为产物：
  描述：

  1-(3-呋喃基)-2-硝基乙烯 、 tert-butyl-[(2E)-4-[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]-3-methylpenta-2,4-dienoxy]-dimethylsilane 在 sodium acetate 、 溶剂黄146 作用下， 生成 (2R,3S,4R,5R)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(furan-3-yl)-2-methyl-4-nitrocyclohexan-1-one
  参考文献：
  名称：

  Cycloaddition Reactions of Chiral 2-Amino-1,3-butadienes with Nitroalkenes:  Synthesis of Enantiomerically Pure 4-Nitrocyclohexanones¹

  摘要：

  2-Amino-1,3-butadienes bearing commercially available S-(+)-2-(methoxymethyl)pyrrolidine as chiral auxiliary undergo a [4 + 2] cycloaddition reaction with nitroalkenes to furnish 4-nitrocyclohexanones upon hydrolysis of the resulting enamine. The cycloadducts are obtained with good yields and very high enantiomeric excesses. The reaction has been performed with aromatic and aliphatic conjugated nitroalkenes. Moreover, a 2-amino diene which features a (Z) double bond undergoes a Michael addition reaction with nitroalkenes, which gives rise to open chain compounds with high enantioselectivity. After acidic hydrolysis, the open chain compounds cyclize to form chiral substituted furans.

  DOI：

  10.1021/jo970237m

文献信息

• Cycloaddition Reactions of Chiral 2-Amino-1,3-butadienes with Nitroalkenes:  Synthesis of Enantiomerically Pure 4-Nitrocyclohexanones¹
  作者：José Barluenga、Fernando Aznar、Cristina Ribas、Carlos Valdés

  DOI：10.1021/jo970237m

  日期：1997.10.1

  2-Amino-1,3-butadienes bearing commercially available S-(+)-2-(methoxymethyl)pyrrolidine as chiral auxiliary undergo a [4 + 2] cycloaddition reaction with nitroalkenes to furnish 4-nitrocyclohexanones upon hydrolysis of the resulting enamine. The cycloadducts are obtained with good yields and very high enantiomeric excesses. The reaction has been performed with aromatic and aliphatic conjugated nitroalkenes. Moreover, a 2-amino diene which features a (Z) double bond undergoes a Michael addition reaction with nitroalkenes, which gives rise to open chain compounds with high enantioselectivity. After acidic hydrolysis, the open chain compounds cyclize to form chiral substituted furans.
• Synthesis of Enantiomerically Pure Functionalized <i>cis</i>- and <i>trans</i>-2-Aminocyclohexanecarboxylic Acid Derivatives
  作者：José Barluenga、Fernando Aznar、Cristina Ribas、Carlos Valdés

  DOI：10.1021/jo981511v

  日期：1998.12.1