2-methyl-6-nitrocyclohexan-1-one | 81842-53-7

• 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: 2-methyl-6-nitrocyclohexan-1-one
• CAS: 81842-53-7
• 化学式: C₇H₁₁NO₃
• 分子量: 157.169
• InChiKey: HYCOIAFXVYRZBA-UHFFFAOYSA-N

物化性质

• 沸点：
  273.5±29.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methyl-6-nitrocyclohexan-1-one 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 3.0h， 生成 Acetic acid 2-methyl-6-nitro-cyclohexyl ester
  参考文献：
  名称：

  一种新型，高效的共轭硝基环烯烃的合成方法

  摘要：

  在回流的二氯甲烷中，通过碱性氧化铝/ DMAP的乙酰化和脱氢乙酰化作用，将硼氢化钠还原α-硝基环烷酮，然后将所得的β-硝基链烷醇连续脱水，一锅法制得共轭硝基环烯烃。

  DOI：

  10.1016/s0040-4039(00)77291-1

文献信息

• Direct Synthesis of Keto Nitroaliphatics via Retro-Henry Reaction of Cyclic 2-Nitroalcohols by Anhydrous Copper Sulfate Adsorbed on Silica Gel. A Short Synthesis of (±)-Phoracantholide I
  作者：Anil K. Saikia、Monoj J. Hazarika、Nabin C. Barua、Maitreyee Sarma Bezbarua、Ram P. Sharma、Anil C. Ghosh

  DOI：10.1055/s-1996-4318

  日期：1996.8

  It has been observed that anhydrous CuSO4 adsorbed on silica gel effects the C-C bond cleavage between the hydroxy group and the nitro group of 2-nitroalcohols. In the case of 2-nitrocyclohexanols, the products are RCO(CH2)4CH2NO2 where R is alkyl, aryl, etc. This strategy has been applied for a short synthesis of (±)-phoracantholide I.

  已经观察到无水CuSO4吸附在硅胶上可以促进2-硝基醇中羟基和硝基之间的C-C键断裂。对于2-硝基环己醇，产物为RCO(CH2)4CH2NO2，其中R是烷基、芳基等。这一策略已应用于(±)-phoracantholide I的短合成中。
• An organocatalytic cascade reaction of 2-nitrocyclohexanone and α,β-unsaturated aldehydes with unusual regioselectivity
  作者：Yi-ning Xuan、Zhen-yu Chen、Ming Yan

  DOI：10.1039/c4cc04298k

  日期：——

  organocatalytic cascade reaction of 2-nitrocyclohexanone and alpha,beta-unsaturated aldehydes was developed. Bicyclo[3.3.1]nonanone products were obtained with good yields and excellent enantioselectivities. The reaction occurred with unusual regioselectivity. A dienolate-iminium activation mechanism was proposed. The products were transformed to eight-membered cyclic ketones with high enantioselectivity

  开发了2-硝基环己酮和α，β-不饱和醛的有机催化级联反应。获得具有良好收率和优异对映选择性的双环[3.3.1]壬酮产物。反应以异常的区域选择性发生。提出了一种二烯酸酯-亚铵盐活化机制。将产物转化为具有高对映选择性的八元环酮。
• α-Nitro ketones 7:1 synthesis of conjugated nitrocyclohexenes
  作者：Pimchit Dampawan、Walter W. Zajac

  DOI：10.1016/s0040-4039(00)86767-2

  日期：1982.1

  The reduction of 2-nitrocyclohexanones to the 2-nitrocyclohexanols with sodium borohydride followed by treatment of the β-nitroalcohols with sodium hydride and subsequent acidification of the salts leads to the regioselective synthesis of conjugatednitrocyclohexenes from cyclohexanones.

  用硼氢化钠将2-硝基环己酮还原为2-硝基环己醇，然后用氢化钠处理β-硝基醇，然后将其酸化，从而由环己酮进行区域选择性合成共轭硝基环己烯。
• Retro Claisen cleavage of α-nitrocycloalkanones using trimethylsilylmethylmagnesium chloride (Peterson reagent): Synthesis of functionalized β-keto-trimethylsilanes.
  作者：Roberto Ballini、Giuseppe Bartoli、Riccardo Giovannini、Enrico Marcantoni、Marino Petrini

  DOI：10.1016/s0040-4039(00)73688-4

  日期：1993.5

  Beta-ketosilanes, bearing a nitro functionality, can be prepared by nucleophilic ring cleavage of alpha-nitrocycloalkanones with the Peterson reagent. This high yielding process shows considerable chemoselectivity but fails with large rings (C(n)>7). This unusual reactivity is tentatively explained considering the silicon beta effect.
• Ballini Roberto, Palestini Corrado, Tetrahedron Lett, 35 (1994) N 31, S 5731-5734
  作者：Ballini Roberto, Palestini Corrado

  DOI：——

  日期：——