(S)-4-(4-bromophenyl)-5-nitropentan-2-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-4-(4-bromophenyl)-5-nitropentan-2-one
• 英文别名: (4S)-4-(4-bromophenyl)-5-nitropentan-2-one
• 化学式: C₁₁H₁₂BrNO₃
• 分子量: 286.125
• InChiKey: OXMTWLYQHOHPJP-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (3S)-1',1'-dimethylethyl 2-acetyl-4-nitro-3-(4-bromophenyl)butyrate 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 4.0h， 生成 (S)-4-(4-bromophenyl)-5-nitropentan-2-one
  参考文献：
  名称：

  Ni(II)−双[(R,R)-N,N'-二苄基环己烷-1,2-二胺]Br2催化1,3-二羰基化合物对共轭硝基烯烃的对映选择性迈克尔加成

  摘要：

  1,3-二羰基化合物与硝基烯烃的高度对映选择性迈克尔加成已经开发出来，它采用了新开发的Ni（II）-（双）二胺基催化剂。反应范围包括取代和未取代的丙二酸酯、β-酮酯和带有芳香族和脂肪族残基的硝基烯烃。值得注意的是该复合物易于合成。

  DOI：

  10.1021/ja052935r

文献信息

• Enantioselective Conjugate Addition of Both Aromatic Ketones and Acetone to Nitroolefins Catalyzed by Chiral Primary Amines Bearing Multiple Hydrogen-Bonding Donors
  作者：Zhong-Wen Sun、Fang-Zhi Peng、Ze-Qian Li、Li-Wei Zou、Shao-Xiong Zhang、Xiang Li、Zhi-Hui Shao

  DOI：10.1021/jo300011x

  日期：2012.4.20

  of chiral primary amine catalysts bearing multiple hydrogen-bonding donors have been designed and synthesized. The newly developed bifunctional organocatalysts efficiently catalyzed not only enantioselective conjugate addition of aromatic ketones to nitroolefins in good yields (up to 87%) with excellent enantioselectivities (97→99% ee) but also enantioselective conjugate addition of acetone to nitroolefins

  设计并合成了带有多个氢键供体的新型手性伯胺催化剂。新开发的双功能有机催化剂不仅能以良好的收率（97→99％ee）以良好的收率（高达87％）高效催化芳族酮对硝基烯烃的对映选择性共轭加成，而且还能以优异的收率（90催化丙酮）将丙酮对硝基选择性共轭加成。 –96％）具有高对映选择性（高达97％ee）。
• A Novel Bifunctional Sulfonamide Primary Amine-Catalyzed Enantioselective Conjugate Addition of Ketones to Nitroolefins
  作者：Fei Xue、Shilei Zhang、Wenhu Duan、Wei Wang

  DOI：10.1002/adsc.200800445

  日期：2008.10.6

  The enantioselective conjugate addition of a variety of ketones to nitroolefins has been developed. The process is efficiently catalyzed by a novel bifunctional sulfonamide primary amine in good yields and with good levels of enantioselectivity.

  已经开发了多种酮向硝基烯烃的对映选择性共轭加成。新型双官能磺酰胺伯胺可有效催化该过程，且收率和对映选择性均良好。
• Highly enantioselective Michael addition of acetone to nitroolefins catalyzed by chiral bifunctional primary amine-thiourea catalysts with acetic acid
  作者：Qing Gu、Xing-Tao Guo、Xin-Yan Wu

  DOI：10.1016/j.tet.2009.04.087

  日期：2009.7

  Highly enantioselective Michael reaction of acetone with a variety of nitroolefins catalyzed by N-[(1R,2R)-2-aminocyclohexyl]-N′-(2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl)-thiourea (1b) together with acetic acid is described. The Michael addition products were obtained in high yields (76–94%) and up to 96% ee.

  N -[（1 R，2 R）-2-氨基环己基] -N '-（2,3,4,6-四-O-乙酰基-β- d催化的丙酮与多种硝基烯烃的高度对映选择性迈克尔反应描述了-吡喃葡萄糖基）-硫脲（1b）与乙酸。迈克尔加成产物的收率很高（76-94％），ee最高可达96％。
• Highly Enantioselective Michael Addition of Acetone to Nitro Olefins Catalyzed by Chiral Bifunctional Primary Amine-Thiophosphoramide Catalyst
  作者：Aidang Lu、Tao Liu、Ronghua Wu、Youming Wang、Zhenghong Zhou、Guiping Wu、Jianxin Fang、Chuchi Tang

  DOI：10.1002/ejoc.201000945

  日期：2010.10

  A series of bifunctional primary amine-thiophosphoramides were synthesized, which proven to be effective organocatalysts for the asymmetric Michael reaction of acetone to both aryl and alkyl nitro olefins in the presence of phenol as a protic additive. The corresponding adducts were obtained in excellent chemical yields (up to >99 %) with excellent enantioselectivities (up to 97 % ee).

  合成了一系列双功能伯胺-硫代磷酰胺，证明是在苯酚作为质子添加剂存在下丙酮与芳基和烷基硝基烯烃的不对称迈克尔反应的有效有机催化剂。相应的加合物以优异的化学产率（高达 > 99 %）和优异的对映选择性（高达 97 % ee）获得。
• Noyori's Ts-DPEN Ligand: Simple yet Effective Catalyst for the Highly Enantioselective Michael Addition of Acetone to Nitroalkenes
  作者：Lin Peng、Xiao-Ying Xu、Liang-Liang Wang、Jun Huang、Jian-Fei Bai、Qing-Chun Huang、Li-Xin Wang

  DOI：10.1002/ejoc.200901509

  日期：2010.4

  Highly enantioselective Michael addition of acetone to a variety of nitroalkenes promoted by simple chiral primary amine bifunctional catalysts (e.g., Noyori's Ts-DPEN ligand) together with terephthalic acid in excellent yields (84-99 %) and enantioselectivities (93―98 % ee) is reported.

  在简单的手性伯胺双功能催化剂（例如 Noyori 的 Ts-DPEN 配体）和对苯二甲酸的促进下，丙酮与各种硝基烯烃的高度对映选择性迈克尔加成反应，以优异的产率 (84-99%) 和对映选择性 (93-98% ee)被报道。