(S)-3-(furan-2-yl)-4-methyl-4-nitro-1-phenyl-pentan-1-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-3-(furan-2-yl)-4-methyl-4-nitro-1-phenyl-pentan-1-one
• 英文别名: (S)-3-(furan-2-yl)-4-methyl-4-nitro-1-phenylpentan-1-one；(3S)-3-(furan-2-yl)-4-methyl-4-nitro-1-phenylpentan-1-one
• 化学式: C₁₆H₁₇NO₄
• 分子量: 287.315
• InChiKey: HNWYXRFEAVRLLG-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  76
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (2E)-3-(2-呋喃基)-1-苯基-2-丙烯-1-酮 、 2-硝基丙烷 在 2Br^(1-)*C₉₀H₆₈F₂₄N₂⁽²⁺⁾ 、 potassium carbonate 作用下， 以 甲苯 为溶剂， 以98%的产率得到(S)-3-(furan-2-yl)-4-methyl-4-nitro-1-phenyl-pentan-1-one
  参考文献：
  名称：

  通过调节相转移催化剂的构象柔性来逆转对映选择性

  摘要：

  朝着完美的不对称催化方向发展：当将二元醇衍生的N螺环季铵盐用作向烷烃及其类似物共轭添加硝基烷烃的相转移催化剂时，观察到了令人感兴趣的对映选择性逆转。已经设计并合成了新型手性催化剂（参见结构）。

  DOI：

  10.1002/anie.200906814

文献信息

• Asymmetric Michael Addition Catalyzed by d-Glucose-based Azacrown Ethers
  作者：Tibor Novák、János Tatai、Péter Bakó、Mátyás Czugler、György Keglevich、László Tóke

  DOI：10.1055/s-2001-11395

  日期：——

  Novel sugar-based azacrown ethers with phosphinoxidoalkyl side chain (2 a - e) have been synthesized. They show significant asymmetric induction as phase transfer catalysts in the Michael addition of 2-nitropropane to chalcone (95% ee) and to 3-fur-2-yl-1-phenyl-propenone (80% ee).

  我们合成了具有膦酰氧基烷基侧链（2 a - e）的新型糖基氮杂环醚。在 2-硝基丙烷与查尔酮（95% ee）和 3-呋喃-2-基-1-苯基-丙烯酮（80% ee）的迈克尔加成反应中，它们作为相转移催化剂显示出明显的不对称诱导作用。
• Enantioselective Michael addition of 2-nitropropane to chalcone analogues catalyzed by chiral azacrown ethers based on α-d-glucose and d-mannitol
  作者：Tibor Bakó、Péter Bakó、György Keglevich、Nikoletta Báthori、Mátyás Czugler、János Tatai、Tibor Novák、Gyula Parlagh、László Tőke

  DOI：10.1016/s0957-4166(03)00351-3

  日期：2003.7

  The chiral monoaza-15-crown-5 type lariat ethers 1 and 2 derived from alpha-(D)-glucose and from (D)-mannitol, respectively, have been applied as phase transfer catalysts in the enantioselective Michael addition of 2-nitropropane to aromatic 3b-c and heteroaromatic 3d-h chalcone analogues. Among the catalysts, the glucose-based le with a phosphinoxidobutyl side arm proved to be the most effective, it inducing 34% e.e. for 4b, 59% e.e. for 4c, 80% e.e. for 4d, 64% e.e. for 4e, 17% e.e. for 4f. Catalyst la having 3-hydroxypropyl substituent resulted in 81% e.e. for compound 4g. The formation of the (+)-(S)-enantiomer of 4 was preferred using crown ethers 1a-c, while the (-)-(R)-enantiomer was in excess with catalyst 2. The absolute configuration of the Michael adduct 4d was determined by single-crystal X-ray analysis. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Reversal of Enantioselectivity by Tuning the Conformational Flexibility of Phase-Transfer Catalysts
  作者：Ming-Qing Hua、Han-Feng Cui、Lian Wang、Jing Nie、Jun-An Ma

  DOI：10.1002/anie.200906814

  日期：2010.4.1

  Towards perfect asymmetric catalysis: When binol‐derived N‐spiro quaternary ammonium salts were used as phase‐transfer catalysts in the conjugate addition of nitroalkanes to chalcones and its analogues, an intriguing reversal of enantioselectivity was observed. Novel chiral catalysts have been designed and synthesized (see structure).

  朝着完美的不对称催化方向发展：当将二元醇衍生的N螺环季铵盐用作向烷烃及其类似物共轭添加硝基烷烃的相转移催化剂时，观察到了令人感兴趣的对映选择性逆转。已经设计并合成了新型手性催化剂（参见结构）。