(4R)-5-nitro-4-(1-naphthalenyl)pentan-2-one | 1231764-00-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (4R)-5-nitro-4-(1-naphthalenyl)pentan-2-one
• 英文别名: (R)-4-(naphthalen-1-yl)-5-nitropentan-2-one；4-(naphthalen-1-yl)-5-nitropentan-2-one
• CAS: 1231764-00-3
• 化学式: C₁₅H₁₅NO₃
• 分子量: 257.289
• InChiKey: CQMXLIFVZVPDFK-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.18
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  60.21
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  在 三乙胺 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 生成 (4R)-5-nitro-4-(1-naphthalenyl)pentan-2-one
  参考文献：
  名称：

  α-硝基乙酸酯与 α,β-不饱和烯酮的有机催化对映选择性迈克尔加成：获得手性 γ-硝基酮和 δ-酮酯的途径

  摘要：

  描述了由手性双功能有机催化剂促进的 α-硝基乙酸酯与 α,β-不饱和烯酮的催化对映选择性共轭加成反应。将 α-硝基乙酸酯处理成 α,β-不饱和烯酮得到了具有高对映选择性的相应迈克尔加合物。共轭加成物很容易转化为手性 γ-硝基酮和 δ-酮酯。

  DOI：

  10.5012/bkcs.2011.32.1.291

文献信息

• Asymmetric Michael addition of ketones to nitroolefins: pyrrolidinyl-oxazole-carboxamides as new efficient organocatalysts
  作者：Ahmed Kamal、Manda Sathish、Vunnam Srinivasulu、Jadala Chetna、Kunta Chandra Shekar、Shalini Nekkanti、Yellaiah Tangella、Nagula Shankaraiah

  DOI：10.1039/c4ob01223b

  日期：——

  Chiral pyrrolidinyl-oxazole-carboxamides were synthesized and used as efficient new organocatalysts for the asymmetric Michael addition of ketones with nitroalkenes under solvent-free conditions. Gratifyingly, the corresponding Michael adducts were obtained in higher yields (up to 99%) and excellent stereoselectivities (up to >99/1 dr and 99% ee). Transition state models have been proposed to account

  合成了手性吡咯烷基-恶唑-羧酰胺，并将其用作高效的新型有机催化剂，用于在无溶剂条件下将酮与硝基烯烃不对称迈克尔加成。令人欣慰的是，获得了相应的迈克尔加合物，收率更高（高达99％）和出色的立体选择性（高达> 99/1 dr和99％ee）。已经提出过渡态模型来解释这些迈克尔加成反应的高对映选择性和非对映选择性，并且还已经使用密度泛函方法研究了能量学。这些结果支持优先形成的SYN通过的方式-产品反式-β-硝基苯经过重新的-面防烯胺。
• Enantioselective organocatalytic conjugate addition of α-nitroacetate to α,β-unsaturated ketones in water
  作者：Hyoung Wook Moon、Dae Young Kim

  DOI：10.1016/j.tetlet.2010.03.105

  日期：2010.5

  catalytic enantioselective conjugate addition reaction of α-nitroacetate to α,β-unsaturated ketones promoted by chiral bifunctional organocatalysts is described. The treatment of α-nitroacetate to α,β-unsaturated ketones under aqueous-phase reaction conditions afforded the corresponding Michael adducts with high enantioselectivity. The conjugate addition adducts are easily converted to chiral δ-keto nitroalkanes

  描述了α-硝基乙酸与由手性双官能有机催化剂促进的α，β-不饱和酮的催化对映选择性共轭加成反应。在水相反应条件下将α-硝基乙酸酯处理为α，β-不饱和酮，得到具有高对映选择性的相应的迈克尔加合物。共轭加合物容易转化为手性δ-酮硝基烷和δ-酮酯。
• Effective asymmetric Michael addition of acetone to nitroalkenes promoted by chiral proline amide-thiourea bifunctional catalysts
  作者：Qiao-wei Wang、Lin Peng、Ji-ya Fu、Qing-chun Huang、Li-xin Wang、Xiao-ying Xu

  DOI：10.3998/ark.5550190.0011.229

  日期：——

  A series of secondary amine-thiourea catalysts 1a-1d derived from L-proline and chiral diamine were prepared and successfully applied to the Michael addition of acetone to trans-nitroalkenes in excellent yields (up to 99%) and enantioselectivities (44-91% ee).

  制备了一系列衍生自 L-脯氨酸和手性二胺的仲胺-硫脲催化剂 1a-1d 并成功应用于丙酮与反式硝基烯烃的迈克尔加成反应，产率高达 99%，对映选择性（44-91%） ee)。
• Asymmetric Michael addition of acetone to β-nitrostyrenes catalyzed by novel organocatalysts derived from D-isomannide or L-isoidide
  作者：Ling-Yan Chen、Stéphane Guillarme、Andrew Whiting、Christine Saluzzo.

  DOI：10.3998/ark.5550190.p008.429

  日期：——

  Novel bifunctional organocatalysts were prepared from D-isomannide or L-isoidide in three steps. These catalysts were then evaluated in the asymmetric Michael addition of acetone to trans--nitrostyrenes. Although moderate enantioselectivities were observed, this study has highlighted that a simple chiral primary diamine can catalyze this reaction. Furthermore, the reaction was also performed with

  新型双功能有机催化剂由 D-异甘露醇或 L-异甘露醇分三步制备。然后在丙酮与反式--硝基苯乙烯的不对称迈克尔加成反应中评估这些催化剂。尽管观察到了中等的对映选择性，但这项研究强调了简单的手性伯二胺可以催化该反应。此外，该反应还使用异甘露醇衍生的二亚胺进行，该二亚胺在酸性条件下原位转化为活性催化剂，导致最佳对映选择性。