3-methyl-1-nitrocyclohex-1-ene | 68216-48-8

• 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-1-nitrocyclohex-1-ene
• 英文别名: 3methyl-1-nitrocyclohexene；1-Nitro-3-methylcyclohexen；3-Methyl-1-nitrocyclohexene
• CAS: 68216-48-8
• 化学式: C₇H₁₁NO₂
• 分子量: 141.17
• InChiKey: VKZQKFWARIXSOX-UHFFFAOYSA-N

物化性质

• 沸点：
  76 °C(Press: 1.5 Torr)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 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-1-nitrocyclohex-1-ene 在 叔丁基过氧化氢 、 samarium diiodide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 、 乙二醇 为溶剂， 反应 42.58h， 生成 1,4-Dimethyl-4,5,6,7-tetrahydro-2H-isoindole
  参考文献：
  名称：

  Synthesis of Cycloprodigiosin Identifies the Natural Isolate as a Scalemic Mixture

  摘要：

  The enantiomers of the natural product cycloprodigiosin were prepared using an expedient five-step synthetic sequence that takes advantage of a Schollkopf-Barton-Zard (SBZ) pyrrole annulation with a chiral isocyanoacetate and a nitrocyclohexene derivative. Using chiral HPLC and X-ray crystallographic analyses of the synthetically prepared Material and natural isolate (isolated from the marine bacterium Pseudoalteromonas rubra), naturally occurring cyclo-prodigiosin was determined to be a scalemic mixture occurring in an enantiomeric ratio of 83:17 (R)/(S) at C4'.

  DOI：

  10.1021/acs.orglett.5b01527
• 作为产物：
  描述：

  3-甲基-1-环己烯 生成 3-methyl-1-nitrocyclohex-1-ene
  参考文献：
  名称：

  A new synthesis of conjugated nitro cyclo olefins, unusually versatile synthetic intermediates

  摘要：

  DOI：

  10.1021/ja00487a088

文献信息

• A new, highly efficient synthesis of conjugated nitrocycloalkenes
  作者：Roberto Ballini、Corrado Palestini

  DOI：10.1016/s0040-4039(00)77291-1

  日期：1994.8

  α-nitrocycloalkanones and successive dehydration of the obtained β-nitroalkanols, by acetylation and dehydroacetylation with basic alumina/DMAP, in refluxing dichloromethane, affords, in one-pot procedure, conjugated nitrocycloalkenes.

  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。
• 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。
• Process for producing beta-nitro-enamines and intermediates thereof
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：EP0672646A1

  公开（公告）日：1995-09-20

  Disclosed is a process for producing a β-nitroenamine compound represented by the formula I: wherein R₁ and R₂ are the same or different and independently indicate a hydrogen atom or a straight-chain or branched C₁-C₁₀ alkyl group which may be optionally substituted with at least one group selected from the group consisting of a halogen atom, a lower alkoxy group, an aryloxy group, hydroxyl group or an aryl group, or an aryl group which may be optionally substituted with at least one group selected from the group consisting of a halogen atom, a lower alkyl group, a lower alkoxy group, an aryl group, an aryloxy group, a nitro group, a cyano group, an acylamino group, a lower dialkylamino group, an arylamino group, a hydroxyl group, an arylsulfonyl group, a mercapto group, a lower alkylthio group or an arylthio group, and R₁ and R₂ may bond together to form a cycloalkyl or bicycloalkyl group; and R₃ is a hydrogen atom, a lower alkyl group, a cycloalkyl group or an aralkyl group; and an intermediate for producing the β-nitroenamine compound.

  本发明公开了一种生产由式 I 代表的 β-硝基烯胺化合物的工艺： 其中R₁和R₂相同或不同，且独立地表示氢原子或直链或支链C₁-C₁₀烷基，该烷基可任选被至少一个选自由卤素原子、低级烷氧基、芳氧基、羟基或芳基组成的组中的基团取代，或可任选被至少一个选自由卤素原子、低级烷氧基、芳氧基、芳氧基、羟基或芳基组成的组中的基团取代的芳基、低级烷基、低级烷氧基、芳基、芳氧基、硝基、氰基、酰氨基、低级二烷基氨基、芳氨基、羟基、芳磺酰基、巯基、低级烷硫基或芳硫基，且 R₁ 和 R₂ 可键合在一起形成环烷基或双环烷基；和 R₃ 是氢原子、低级烷基、环烷基或芳烷基；以及生产 β-硝基烯胺化合物的中间体。
• .alpha.-Nitro keto hydrazone and keto imine dianions. Synthetic equivalents for the nitroalkene d3 synthon
  作者：Scott E. Denmark、Jeffrey A. Sternberg、Rainer Lueoend

  DOI：10.1021/jo00241a024

  日期：1988.3
• Ballini Roberto, Palestini Corrado, Tetrahedron Lett, 35 (1994) N 31, S 5731-5734
  作者：Ballini Roberto, Palestini Corrado

  DOI：——

  日期：——