aci-1-nitropropane sodium salt | 12384-98-4

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: aci-1-nitropropane sodium salt
• 英文别名: 1-nitropropane sodium salt；1-nitro-propane; sodium salt；1-nitro-propane; sodium-salt；1-Nitro-propan; Natrium-Salz；1-Propannitronat-natrium；sodium;1-nitropropane
• CAS: 12384-98-4
• 化学式: C₃H₆NO₂*Na
• 分子量: 111.076
• InChiKey: SOZROHGWPCKAQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.52
• 重原子数：
  7.0
• 可旋转键数：
  1.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  49.13
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  aci-1-nitropropane sodium salt 、 alkaline earth salt of/the/ methylsulfuric acid 以 乙醇 为溶剂， 反应 30.0h， 以62%的产率得到4-methyl-3-nitrotridecane
  参考文献：
  名称：

  钴氧肟介导的自由基烷基-硝基烷基阴离子的交叉偶联

  摘要：

  烷基钴肟肟RCo III（dmgH ）2 py（dmgH =二甲基乙二肟单阴离子）和硝基烷基阴离子的乙醇水溶液的厌氧光解引起交叉偶联，其中与硝基的Hα被R取代。

  DOI：

  10.1016/s0040-4039(00)82393-x
• 作为产物：
  描述：

  硝基丙烷 在 sodium hydroxide 作用下， 以 水 为溶剂， 生成 aci-1-nitropropane sodium salt
  参考文献：
  名称：

  α-硝基hydr：从伯硝基化合物形成膦酸酯衍生物的通用中间体

  摘要：

  通过与芳基重氮盐偶合，然后与亚磷酸酯进行Arbuzov型反应，伯硝基化合物很容易转化为肼代膦酸酯衍生物。

  DOI：

  10.1016/s0040-4039(02)00208-3
• 作为试剂：
  描述：

  2-硝基苯硫氯 在 乙醚 、 aci-1-nitropropane sodium salt 作用下， 生成 (2-nitro-phenyl)-(1-nitro-propyl)-sulfide
  参考文献：
  名称：

  Derivatives of Sulfenic Acids. VI. The Synthesis of α-Nitro Sulfides

  摘要：

  DOI：

  10.1021/ja01152a091

文献信息

• Some CC bond constructions on monosaccharides using cobaloxime-mediated radical alkyl-nitroalkylanion cross coupling reactions
  作者：Bruce P. Branchaud、Gui-Xue Yu

  DOI：10.1016/s0040-4039(00)79754-1

  日期：1991.7

  The formation of monosaccharide cobaloximes and their cross coupling reactions with nitroalkyl anions are demonstrated to be useful in CC bond constructions to produce branched-chain monosaccharides.

  已证明单糖钴肟的形成及其与硝基烷基阴离子的交叉偶联反应可用于CC键结构中以生产支链单糖。
• Michael Type Additions with Nitroparaffins.¹ A Convenient Route to Nitrocyclohexanols
  作者：HENRY FEUER、RONALD HARMETZ

  DOI：10.1021/jo01063a022

  日期：1961.4
• Friedel-Crafts-type reactions involving di- and tricationic species. Onium-allyl dications and O,O-diprotonated aci-nitro species bearing a protonated carbonyl group
  作者：Tomohiko Ohwada、Naoko Yamagata、Koichi Shudo

  DOI：10.1021/ja00004a044

  日期：1991.2

  Stable carbocations do not react with nonactivated benzenes. For example, acetophenone does not react with benzene in the presence of trifluoromethanesulfonic acid (TFSA), while trifluoroacetophenone does do so under acidic conditions owing to activation of the electrophilicity of the hydroxycarbenium cation by the trifluoromethyl group. This and other studies suggest that an electron-withdrawing substituent on the cationic center increases the reactivity toward benzenes. In this paper, involvement of multiply positively charged (dicationic and tricationic) species, which have sufficient electrophilicity toward benzene, is demonstrated in the acid-catalyzed reactions of cinnamaldehyde and its derivatives and also in the acid-catalyzed reactions of nitromethanes. The species formed from cinnamaldehyde, cinnamaldimine, cinnamaldoxime, and their derivatives in TFSA or TFSA-SbF5 have an adequate reactivity toward benzene. O-Protonated cinnamaldehyde and its derivatives, N-protonated cinnamaldimine, and N,N-dimethylcinnamaldiminium salt do not react with benzene. Since a strong acid catalyst is required for the reactions, participation of doubly protonated species, onium-allyl dications, is proposed. Ab initio calculations of (1) the donor-acceptor interaction energies of a neutral donor (such as water and ammonia) and a doubly charged allyl dication and (2) proton affinities demonstrated that the ammonium-allyl dication is more stable than the oxonium-allyl dication, in accordance with the experimental observation. Nitronic acids also react with benzene at the ipso position with respect to the nitro group to give the phenylated oximes in the presence of TFSA. The reaction with benzene is not catalyzed by trifluoroacetic acid, which is sufficiently acidic to monoprotonate a nitronic acid to the protonated aci-nitro form. The reaction requires a stronger acid, trifluoromethanesulfonic acid, suggesting intervention of the dication formed by O,O-diprotonation of aci-nitroalkanes rather than the monoprotonated aci-nitroalkane. As a result of further study on the phenylation reactions, we found a facile phenylation reaction of nitromethanes substituted with an electron-withdrawing group, catalyzed by TFSA, to give phenylated alpha-carbonyloximes in high yields. A triply positively charged cation, an O,O-diprotonated aci-nitro species bearing a protonated ethoxycarbonyl group, which can react with nonactivated benzene, is proposed to be an intermediate in this reaction.
• Method of producing carboxylic acids from nitrohydrocarbons
  申请人：COMMERCIAL SOLVENTS CORP

  公开号：US02113813A1

  公开（公告）日：1938-04-12
• Lippincott; Hass, Industrial and Engineering Chemistry, 1939, vol. 31, p. 119
  作者：Lippincott、Hass

  DOI：——

  日期：——