3-methyl-3-nitro-1-butene | 1809-67-2

• 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: 3-methyl-3-nitro-1-butene
• 英文别名: 3-methyl-3-nitrobut-1-ene
• CAS: 1809-67-2
• 化学式: C₅H₉NO₂
• 分子量: 115.132
• InChiKey: XKNWVDRBOMGBKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-methyl-3-nitro-1-butene 在 氢气 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 生成 3-amino-1-(dimethylamino)-3-methylbutan-2-ol
  参考文献：
  名称：

  Novel 3-chlorooxazolidin-2-ones as antimicrobial agents

  摘要：

  Antimicrobial resistance against many known therapeutics is on the rise. We examined derivatives of 3-chlorooxazolidin-2-one 1a (X = H) as antibacterial and antifungal agents. The key findings were that the activity and apparent in vitro cytotoxicity could be controlled by the substitution of charged solubilizers at the 4- and 5-positions. These changes both significantly increase the antifungal potency and decrease cytotoxicity. Particularly effective were trialkylammonium groups which led to 400- to 600-fold increases in the antifungal therapeutic index when compared to their unsubstituted counterparts. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.03.036
• 作为产物：
  描述：

  ethyl 4-methyl-4-nitro-pentanoate 在 sodium hydroxide 、 苄基三乙基氯化铵 、 苯乙腈 作用下， 生成 3-methyl-3-nitro-1-butene
  参考文献：
  名称：

  Makosza,M.; Jawdosiuk,M., Bulletin de l'Academie Polonaise des Sciences, Serie des Sciences Chimiques, 1968, vol. 16, p. 597 - 600

  摘要：

  DOI：

文献信息

• Lewis acid-induced nucleophilic substitution reactions of aliphatic nitro compounds with carbon nucleophiles
  作者：Noboru Ono、Tetsuya Yanai、Akio Kamimura、Aritsune Kaji

  DOI：10.1039/c39860001285

  日期：——

  Tertiary, benzyl, and allylic nitro compounds undergo nuclephilic substitution reactions with carbon nucleophiles such as electron rich aromatic compounds, allylsilanes, or silyl enol ethers in the presence of SnCl4.

  在SnCl 4的存在下，叔，苄基和烯丙基硝基化合物与碳亲核试剂如富电子芳族化合物，烯丙基硅烷或甲硅烷基烯醇醚进行亲核取代反应。
• Regioselective Preparation of Allylic Sulfones by Palladium-Catalyzed Reactions of Allylic Nitro Compounds with Sodium Benzenesulfinate
  作者：Noboru Ono、Isami Hamamoto、Takashi Kawai、Aritsune Kaji、Rui Tamura、Masato Kakihana

  DOI：10.1246/bcsj.59.405

  日期：1986.2

  thermodynamically-stable isomers is negligible. On the other hand, the palladium-catalyzed sulfonylation of allylic acetates with sodium benzenesulfinate is accompanied by the isomerization to give the thermodynamically-controlled products selectively. These results can be explained by assuming that allylic nitro compounds are more reactive to the palladium catalyst than allylic acetates and sulfones.

  在 N,N-二甲基甲酰胺 (DMF) 中 5 mol% Pd(PPh3)4 存在下，在 20–70 °C 下，用苯亚磺酸钠处理烯丙基硝基化合物 1–10 小时，导致形成占优势的烯丙基砜动力学控制的产品。产物分布主要受烯丙基单元取代基的电子性质控制，异构化为热力学稳定的异构体可以忽略不计。另一方面，钯催化的乙酸烯丙酯与苯亚磺酸钠的磺酰化伴随异构化，选择性地得到热力学控制的产物。这些结果可以通过假设烯丙基硝基化合物比烯丙基乙酸酯和砜对钯催化剂更具反应性来解释。
• Regio-and stero-selective γ-substitution of allylic nitro compounds with lithium dialkylcuprates
  作者：Noboru Ono、Isami Hamamoto、Aritsune Kaji

  DOI：10.1039/c39840000274

  日期：——

  Regio-and stereo-selective γ-Substitution of allylic nitro compounds with lithium dialkylcuprates provides a new synthesis for trisubstituted olefins.

  二烷基铜酸锂将烯丙基硝基化合物的区域和立体选择性γ取代为三取代的烯烃提供了新的合成方法。
• Regioselective Monoalkylation of Ketones with Allylic Nitro Compounds
  作者：Noboru Ono、Isami Hamamoto、Aritsune Kaji

  DOI：10.1246/bcsj.58.1863

  日期：1985.6

  Lithium enolates from 2-methylcyclohexanone and p-methylacetophenone react with allylic nitro compounds in the presence of triethylborane (2 equiv) and Pd(PPh3)4 (5 mol%) to give monoallylated compounds regioselectively.

  在三乙基硼烷（2 当量）和 Pd(PPh3)4 (5 mol%) 存在下，2-甲基环己酮和对甲基苯乙酮的锂烯醇化物与烯丙基硝基化合物反应，区域选择性地生成单烯丙基化化合物。
• Nucleophilic addition of secondary nitro compounds to acetylene
  作者：Boris F. Kukharev、Valery K. Stankevich、Galina R. Klimenko

  DOI：10.1070/mc2002v012n02abeh001541

  日期：2002.1

  The products of C-vinylation were prepared in 52–65% yield by the reaction of secondary nitroalkanes with acetylene in DMSO–KOH.

  通过仲硝基烷烃与乙炔在DMSO-KOH中的反应制备C-乙烯基化产物，产率为52-65％。