1-nitro-3-(2-nitroethyl)benzene | 99595-87-6

• 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: 1-nitro-3-(2-nitroethyl)benzene
• 英文别名: 2-(3-nitrophenyl)-1-nitroethane
• CAS: 99595-87-6
• 化学式: C₈H₈N₂O₄
• mdl: MFCD03410720
• 分子量: 196.163
• InChiKey: FFBMBNOWZMJDCS-UHFFFAOYSA-N

物化性质

• 熔点：
  115.5-116 °C
• 沸点：
  368.7±25.0 °C(Predicted)
• 密度：
  1.335±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  91.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 1-nitro-3-(2-nitroethyl)benzene 在 sodium acetate 作用下， 以 四氢呋喃 为溶剂， 生成 2-nitro-3-(3-nitrophenyl)propan-1-ol
  参考文献：
  名称：

  可循环使用的有机链反应体系：迈克尔-半缩醛化反应中具有季立体中心的旋光顺式-δ-Lactols的立体选择性沉淀。

  摘要：

  描述了β-取代的β-硝基乙醇与α，β-不饱和醛之间的级联迈克尔-半缩醛化反应，它为具有四级立体中心的顺式-δ-内酯提供了方便高效的合成方法，具有中等收率和优异的对映选择性。基于通过过滤分离出的顺式-δ-内酯的选择性沉淀，滤液中的催化体系可以直接重复使用并循环八次，而对映选择性没有任何明显的下降。

  DOI：

  10.1002/adsc.201000553
• 作为产物：
  描述：

  2-硝基-1-(3-硝基苯基)乙酸乙酯 在 sodium tetrahydroborate 、 溶剂黄146 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 生成 1-nitro-3-(2-nitroethyl)benzene
  参考文献：
  名称：

  Metal-directed synthesis of aminobenzyl polyaza macrecycles: candidates for attachment to polymers and biomolecules

  摘要：

  Copper(II)-directed condensation between 4,7-diazadecane-1,10-diamine, formaldehyde and 1-nitro-3-(2-nitroethyl)benzene yielded the macrocyclic [10-nitro-10-(3-nitrobenzyl)-1,4,8,12-tetraazacyclopentadecane]copper(II) ion. Reduction (Zn,HCl) gave the pendant-arm macrocycle 10-(3-aminobenzyl)-1,4,8,12-tetraazacyclopentadec-10-ylamine as the hydrochloride salt. Condensation reactions with 1-nitro-4-(2-nitroethyl)benzene and 2-phenylnitroethane were also successful. The capacity of the aminobenzyl C-pendant introduced by this facile chemistry for covalent attachment has been examined by attachment of 10-(3-aminobenzyl)-1,4,8,12-tetraazacyclopentadec-10-ylamine to the acidic cation-exchange resin CM Bio-Gel A and to horse heart cytochrome c, employing a water-soluble carbodiimide coupling agent at pH 5 to promote amide formation. The attachment was probed by copper(II) complexation to the bound macrocycle and subsequent spectroscopic or voltammetric analysis.

  DOI：

  10.1039/dt9940003107

文献信息

• Zeolite (H-ZSM 5)-catalysed reduction of conjugated nitroalkenes with sodium cyanoborohydride
  作者：Anuradha Gupta、Azizul Haque、Yashwant D. Vankar

  DOI：10.1039/cc9960001653

  日期：——

  Conjugated nitroalkenes are readily reduced to the corresponding nitroalkanes with sodium cyanoborohydride in the presence of the zeolite H-ZSM 5 in methanol.

  在甲醇中，配合着H-ZSM 5沸石的存在下，共轭硝基烯烃很容易被氰基硼氢化钠还原为相应的硝基烷烃。
• Heteroaryl-substituted pyrrole derivatives, their preparation and their therapeutic uses
  申请人：SANKYO COMPANY, LIMITED

  公开号：US20040054173A1

  公开（公告）日：2004-03-18

  Compounds having activity against production of an inflammatory cytokine of formula (I)′: 1 A′ is pyrrole; R 1′ is phenyl or naphthyl; R 2′ is pyridyl or pyrimidinyl; R 3′ is (IIa)′, (IIb)′ or (IIc)′: 2 m′ is 1; E′ is nitrogen; D′ is >C(R 5′ )—, R 5′ is hydrogen, Substituent &agr;′ or Substituent &bgr;′; B′ is nitrogen-containing 5-membered heterocyclic; R 4′ is 1 to 3 substituents from Substituent &agr;′, Substituent &bgr;′ and Substituent &ggr;′; R 1′ and R 3′ are bonded to two atoms of the pyrrole adjacent to the pyrrole atom bonded to R 2′ ; Substituent &agr;′ is hydroxyl, nitro, cyano, halogen, alkoxy, halogeno alkoxy, alkylthio, halogeno alkylthio or —NR a′ R b′ ; R a′ and R b′ are hydrogen, alkyl, alkenyl, alkynyl, aralkyl or alkylsulfonyl, or R a′ and R b′ with the nitrogen atom form a heterocyclyl; Substituent &bgr;′ is alkyl, alkenyl, alkynyl, aralkyl or cycloalkyl; Substituent &ggr;′ is oxo, hydroxyimino, alkoxyimino, alkylene, alkylenedioxy, alkylsulfinyl, alkylsulfonyl, aryl, aryloxy, alkylidenyl or aralkylidenyl.

  具有对抗公式(I)′炎症细胞因子生成活性的化合物： 1 A′是吡咯；R 1′ 是苯基或萘基；R 2′ 是吡啶基或嘧啶基；R 3′ 是(IIa)′，(IIb)′或(IIc)′： 2 m′是1；E′是氮；D′是>C(R 5′ )—, R 5′ 是氢，取代基α′或取代基β′；B′是含氮的5-成员杂环；R 4′ 是来自取代基α′，取代基β′和取代基γ′的1至3个取代基；R 1′ 和R 3′ 分别与吡咯环上与R 2′ 相连的吡咯原子的两个相邻原子成键；取代基α′是羟基，硝基，氰基，卤素，烷氧基，卤代烷氧基，烷基亚砜，卤代烷基亚砜或—NR a′ R b′ ；R a′ 和R b′ 是氢，烷基，烯基，炔基，芳烷基或烷基亚磺酰基，或者R a′ 和R b′ 与氮原子形成杂环；取代基β′是烷基，烯基，炔基，芳烷基或环烷基；取代基γ′是氧代，羟基亚胺，烷氧基亚胺，亚烷基，亚烷基二氧，烷基亚磺酰基，烷基亚磺酰基，芳基，芳氧基，亚烷基或芳亚烷基。
• Heteroaryl-substituted pyrrole derivates, their preparation and their therapeutic uses
  申请人：Sankyo Company Limited

  公开号：EP1243589A1

  公开（公告）日：2002-09-25

  Compounds of formula (I): [wherein: A is a pyrrole ring; R1 is an optionally substituted phenyl or naphthyl group; R2 is an optionally substituted pyridyl or pyrimidinyl group; R3 represents a group of the formula -X-R4, wherein X is a single bond or an alkenylene group, and R4 is an optionally substituted nitrogen-containing heterocyclyl group; selected from the group consisting of 8-azabicyclo[3.2.1]octenyl, 9-azabicyclo[3.3.1]nonenyl and quinuclidinenyl groups, PROVIDED THAT said substituents R1 and R3 are bonded to the two atoms of said pyrrole ring which are adjacent to the atom of the pyrrole ring to which said substituent R2 is bonded] have excellent inhibitory activity against the production of inflammatory cytokines.

  化合物的结构式（I）：[其中：A为吡咯环；R1为可选取代的苯或萘基团；R2为可选取代的吡啶或嘧啶基团；R3代表具有下述结构的基团-X-R4，其中X为单键或烯基链，R4为可选取代的含氮杂环基团；所选取自8-氮杂双环[3.2.1]辛烯基、9-氮杂双环[3.3.1]壬烯基和喹啉环基团，前提是所述取代基R1和R3连接到所述吡咯环的两个相邻原子，这两个原子与所述取代基R2连接的吡咯环原子相邻]具有出色的抑制炎症细胞因子产生活性。
• The highly chemoselective transfer hydrogenation of the carbon–carbon double bond of conjugated nitroalkenes by a rhodium complex
  作者：Jing Xiang、Er-Xiao Sun、Chun-Xia Lian、Wei-Cheng Yuan、Jin Zhu、Qiwei Wang、Jingen Deng

  DOI：10.1016/j.tet.2012.04.028

  日期：2012.6

  Chemoselective transfer hydrogenation of conjugated nitroalkenes catalyzed by [RhCl2Cp∗]2–diamine complex (Cp∗=η5-C5Me5) using HCOOH/Et3N (5:2) (TEAF) as a hydrogen source was realized. A variety of nitrostyrenes, β-methyl nitrostyrenes, and 3-methyl-4-nitro-5-alkenyl-isoxazoles were reduced smoothly in good to excellent yields in short reaction time. Other functional groups are inert under the reaction

  通过[催化的RhCl缀合的硝基烯烃化学选择性转移氢化2的Cp * ] 2 -二胺复合物（CP * =η 5 -C 5我5）使用HCOOH / ET 3 N（5：2）（TEAF）作为氢源，实现。各种硝基苯乙烯，β-甲基硝基苯乙烯和3-甲基-4-硝基-5-链烯基-异恶唑均能在短时间内以良好或极好的收率顺利还原。在反应条件下，其他官能团是惰性的。
• Reduction of α,β-unsaturated nitrocompounds with tributyltin hydride.
  作者：J.M. Aizpurua、M. Oiarbide、C. Palomo

  DOI：10.1016/s0040-4039(00)96731-5

  日期：1987.1

  Nitroalkenes upon treatment with tributyltin hydride in the absence of any catalyst provide a new method for the reduction of α,β -unsaturated nitrocompounds. Oxidative cleavage of the intermediate stannyl nitronates yielded carbonyl compounds in good yields.

  在没有任何催化剂的情况下用氢化三丁基锡氢化处理的硝基烯烃提供了一种还原α，β-不饱和硝基化合物的新方法。中间体甲磺酸锡烷基酯的氧化裂解以高收率得到羰基化合物。