(2R,3R,7R)-2,3-Dimethyl-7-(1-methyl-1-nitro-ethyl)-1,4-dioxa-spiro[4.5]decane | 105969-80-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: (2R,3R,7R)-2,3-Dimethyl-7-(1-methyl-1-nitro-ethyl)-1,4-dioxa-spiro[4.5]decane
• 英文别名: (2R,3R,7R)-2,3-dimethyl-7-(2-nitropropan-2-yl)-1,4-dioxaspiro[4.5]decane
• CAS: 105969-80-0
• 化学式: C₁₃H₂₃NO₄
• 分子量: 257.33
• InChiKey: NSLHOANZNLNQBV-GMTAPVOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  64.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-环己烯-1-酮 在 trans-4,5-methano-L-proline 氯仿 、 对甲苯磺酸 、 2,5-dimethyl-piperazine 作用下， 以 苯 为溶剂， 反应 141.0h， 生成 (2R,3R,7R)-2,3-Dimethyl-7-(1-methyl-1-nitro-ethyl)-1,4-dioxa-spiro[4.5]decane
  参考文献：
  名称：

  Optimization of the Catalytic Asymmetric Addition of Nitroalkanes to Cyclic Enones with trans-4,5-Methano-l-proline

  摘要：

  The conjugate addition of symmetrical 2-nitroalkanes to 2-cycloalkenones catalyzed by trans-4,5-methano-L-proline proceeds with > 99% ee and excellent chemical yields. 1-Nitroalkanes afford diastereomeric syn/anti products that can be separated with good individual enantioselectivities. Proline hydroxamic acid and its trans-4,5-methano-L-proline hydroxamic acid are also effective organocatalysts in the addition of 2-nitropropane to 2-cyclohexenone (75% and 81% ee, respectively).

  DOI：

  10.1021/ol0618407

文献信息

• Catalytic Asymmetric Conjugate Addition of Nitroalkanes to Cycloalkenones
  作者：Stephen Hanessian、Vinh Pham

  DOI：10.1021/ol000170g

  日期：2000.9.1

  Nitroalkanes add to cyclic and acyclic enones in an enantioselective manner in the presence of catalytic quantities of L-proline and trans-2,5-dimethylpiperazine as excess additive.

  在催化量的L-脯氨酸和反式2,5-二甲基哌嗪作为过量添加剂存在下，硝基烷以对映选择性的方式添加到环状和无环烯酮中。
• 4-trans-Amino-proline based di- and tetrapeptides as organic catalysts for asymmetric C–C bond formation reactions
  作者：Svetlana B. Tsogoeva、Sunil B. Jagtap、Zoya A. Ardemasova

  DOI：10.1016/j.tetasy.2006.03.012

  日期：2006.3

  4-trans-Amino-proline based di- and tetrapeptides have been successfully applied as chiral organocatalysts in the enantioselective conjugate addition of nitroalkanes to cyclic enones and the direct aldol reaction. Two 4-trans-amino-proline residues were shown to be sufficient enough to catalyze the conjugate addition reactions with up to 88% ee and up to 100% yield. It has been demonstrated that 4-trans-amino-proline based di- and tetrapeptides are significantly more active than L-proline (at 30 mol %) and can catalyze the direct aldol reaction with good yield and enantioselectivity within 3 h and at lower catalyst loading (5 mol %). (c) 2006 Elsevier Ltd. All rights reserved.