2-phenyl-1-nitropentane

• 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: 2-phenyl-1-nitropentane
• 英文别名: 1-Nitropentan-2-ylbenzene
• 化学式: C₁₁H₁₅NO₂
• 分子量: 193.246
• InChiKey: BCNDEYUVHXOCOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯丁酮 在 sodium tetrahydroborate 、 正丁胺 作用下， 以 甲苯 为溶剂， 生成 2-phenyl-1-nitropentane
  参考文献：
  名称：

  Organocatalytic Asymmetric Transfer Hydrogenation of Nitroolefins

  摘要：

  We describe a highly efficient and highly enantioselective Hantzsch ester mediated conjugate transfer hydrogenation of beta,beta-disubstituted nitroolefins that is catalyzed by a Jacobsen-type thiourea catalyst.

  DOI：

  10.1021/ja074045c

文献信息

• Generation of nitroalkanes, hydroximoyl halides and nitrile oxides from the reactions of β-nitrostyrenes with Grignard or organolithium reagents
  作者：Ching-Fa Yao、Kuo-Hsi Kao、Ju-Tsung Liu、Cheng-Ming Chu、Yeh Wang、Wen-Chang Chen、Yu-Mei Lin、Wen-Wei Lin、Ming-Chung Yan、Jing-Yuan Liu、Ming-Ching Chuang、Jin-Lien Shiue

  DOI：10.1016/s0040-4020(97)10356-8

  日期：1998.1

  products 6 and/or 7 are observed if the nitronates, generated from the substrate 1a, are added to 85% aqueous H2SO4 but only the hydrolyzed carboxylic acids 9 are generated when the β-nitrostyrenes 2 are reacted with Grignard reagents and worked up under the same condition. The nitrile oxides 7 can undergo 1,3-dipolar cycloaddition with alkenes or alkynes to generate 2-isoxazolines or isoxazoles. A one-pot

  β型硝基苯乙烯1或2与格氏或有机锂试剂反应在乙醚或THF溶液由1,4-加成中间nitronates以产生甲。当用稀盐酸处理A时，获得高产率的硝基烷3（和肟4）或5。当将中间体A缓慢加入到冰冷的浓氢卤酸中时，可以分离出羟甲酰卤6、8或一氧化氮7。如果从基材1a产生的硝酸盐观察到相同的产物6和/或7。将β-硝基苯乙烯2加入到85％的H 2 SO 4水溶液中，但是当β-硝基苯乙烯2与格氏试剂反应并在相同条件下进行后处理时，仅产生水解的羧酸9。腈氧化物7可与烯烃或炔烃进行1，3-偶极环加成反应以生成2-异恶唑啉或异恶唑。据报道，通过分子内一氧化氮-烯烃环加成反应可以一锅合成[n，3,0]双环（n = 3或4）化合物23-27。
• Metal-Templated Design: Enantioselective Hydrogen-Bond-Driven Catalysis Requiring Only Parts-per-Million Catalyst Loading
  作者：Weici Xu、Marcus Arieno、Henrik Löw、Kaifang Huang、Xiulan Xie、Thomas Cruchter、Qiao Ma、Jianwei Xi、Biao Huang、Olaf Wiest、Lei Gong、Eric Meggers

  DOI：10.1021/jacs.6b02769

  日期：2016.7.20

  octahedral iridium complex, an exceptionally active hydrogen-bond-mediated asymmetric catalyst was developed and its mode of action investigated by crystallography, NMR, computation, kinetic experiments, comparison with a rhodium congener, and reactions in the presence of competing H-bond donors and acceptors. Relying exclusively on weak forces, the enantioselective conjugate reduction of nitroalkenes

  基于使用双环金属化八面体铱配合物形式的刚性球状结构支架的金属模板化方法，开发了一种异常活泼的氢键介导的不对称催化剂，并通过晶体学、核磁共振、计算研究了其作用模式，动力学实验，与铑同类物的比较，以及在竞争性 H 键供体和受体存在下的反应。仅依靠弱力，硝基烯烃的对映选择性共轭还原可以在低至 0.004 mol% (40 ppm) 的催化剂负载下进行，代表高达 20 250 的周转数。催化剂的速率加速为 2.5 × 10(5 ) 确定。催化的起源可追溯到通过精心协调的氢键和催化剂与底物之间的范德华相互作用，有效稳定过渡态电荷。这项研究表明，仅由氢键和范德华相互作用驱动的不对称催化的熟练程度可以通过底物的直接过渡金属配位与传统的活化相媲美。
• [EN] METHOD FOR PRODUCING AN OPTICALLY ACTIVE NITRO COMPOUND<br/>[FR] PROCEDE DE PRODUCTION D'UN COMPOSE NITRO OPTIQUEMENT ACTIF
  申请人：CARREIRA ERICK M

  公开号：WO2004103951A1

  公开（公告）日：2004-12-02

  An optically active nitro compound having two hydrogen atoms on its α-cabon atom and having β-asymmetric carbon atom can be produced by making α, β-unsaturated nitroolefin having a hydrogen atom on its α-cabon atom react with at least two organosilicon compounds having at lest one silicon-hydrogen bond in the molecule in the presence of an asymmetric copper complex, or react with an organosilicon compound having at least one silicon-hydrogen bond in the molecule in the presence of an asymmetric copper complex and water.

  具有两个氢原子的α-碳原子和β-手性碳原子的光学活性硝基化合物可以通过使具有α-碳原子上的氢原子的α，β-不饱和硝基烯烃与至少两个分子中至少有一个硅-氢键的有机硅化合物在存在不对称铜配合物的情况下反应，或者在存在不对称铜配合物和水的情况下，使具有至少一个硅-氢键的有机硅化合物与α-碳原子上的氢原子反应来制备。
• Method for producing an optically active nitro compound
  申请人：Carreira M. Erick

  公开号：US20070037976A1

  公开（公告）日：2007-02-15

  An optically active nitro compound having two hydrogen atoms on its α-cabon atom and having β-asymmetric carbon atom can be produced by making α, β-unsaturated nitroolefin having a hydrogen atom on its α-cabon atom react with at least two organosilicon compounds having at lest one silicon-hydrogen bond in the molecule in the presence of an asymmetric copper complex, or react with an organosilicon compound having at least one silicon-hydrogen bond in the molecule in the presence of an asymmetric copper complex and water.

  具有α-碳原子上两个氢原子和β-不对称碳原子的光学活性硝基化合物可以通过使具有α-碳原子上氢原子的α，β-不饱和硝基烯与至少两种分子中具有至少一个硅-氢键的有机硅化合物在不对称铜配合物存在下反应，或在不对称铜配合物和水存在下与具有至少一个硅-氢键的有机硅化合物反应而制得。
• Additions of organomanganese reagents to conjugated nitroolefins
  作者：I.N.N. Namboothiri、Alfred Hassner

  DOI：10.1016/0022-328x(96)06150-5

  日期：1996.7

  Additions of organomanganese reagents to aromatic and aliphatic conjugated nitroolefins were examined for the first time. In most cases reaction proceeded rapidly at -30 degrees C. Unlike Mn reagents lacking beta-hydrogens (Me, Ph), which lead to oxidative coupling and reductive dimerisation of nitrostyrenes, benzylmanganese chloride gives 1,4-addition in yields exceeding Grignard or Cu-assisted additions. At 0 degrees C alkyl(Bu, Pr)-manganese reagents undergo an addition-migration-elimination process with nitrostyrenes providing a convenient and stereospecific entry into arylated trans-olefins.