(4S,5R)-5-formyl-4-nitro-(3-oxobutyl)cyclohex-1-ene | 361526-21-8

• 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: (4S,5R)-5-formyl-4-nitro-(3-oxobutyl)cyclohex-1-ene
• 英文别名: (4S,5R)-5-formyl-1,2-dimethyl-4-nitro-4-(3''-oxobutyl)cyclohex-1-ene；(1R,6S)-3,4-dimethyl-6-nitro-6-(3-oxobutyl)cyclohex-3-ene-1-carbaldehyde
• CAS: 361526-21-8
• 化学式: C₁₃H₁₉NO₄
• 分子量: 253.298
• InChiKey: ZZXDGMSTQPHYGY-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  80
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S,5R)-5-formyl-4-nitro-(3-oxobutyl)cyclohex-1-ene 在 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 以72%的产率得到2-acetyl-4,7-dihydro-5,6-dimethylindene
  参考文献：
  名称：

  Nitrous acid elimination from 4-alkyl-5-formyl-4-nitrocyclohex-1-enes: synthesis of mono and bicyclic benzene and dihydrobenzene derivatives

  摘要：

  Elimination of nitrous acid from 4-alkyl-5-formyl-4-nitrocyclohex-1-enes, by treatment with silica gel or potassium carbonate, is described. Whereas in the former case the product consisted in a mixture of the starting material, 2-alkyl-4,5dimethylcyclohexa-1,4-diene-1-carbaldehyde and 2-alkyl-4,5-dimethylbenzaldehyde, reaction with potassium carbonate at 60 degreesC yielded exclusively aromatic compounds. Furthermore, when a ketone Function was present in the gamma -position of the ail;yl chain at C-4, the alkaline medium promoted an intramolecular. aldol condensation, bring obtained bicyclic products. PM3 calculations have been made to justify the result of the cyclization. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00828-0
• 作为产物：
  描述：

  (4R,5R)-1,2,3,4,5-penta-O-acetyl-1-C-(1,2-dimethyl-4-nitrocyclohex-1-en-5-yl)-D-manno-pentitol 在 sodium periodate 、 sodium methylate 、 四甲基胍 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 25.75h， 生成 (4S,5R)-5-formyl-4-nitro-(3-oxobutyl)cyclohex-1-ene
  参考文献：
  名称：

  由5-糖基-4-硝基环己基-1-烯制备对映体纯的4-烷基-5-甲酰基-4-硝基环己基-1-烯

  摘要：

  在所有情况下，碱催化（TMG，DBU或TEA）在5-glyco-4-nitrocyclohex-1-enes 1a或1b与许多单或α，β-di取代的缺电子烯烃之间的不对称Michael反应，加合物，其中所述糖侧链和添加的组上C-4的环己烯环的呈反式-relationship。此外，一些加合物已用于通过两步法制备对映体纯的4-烷基-5-甲酰基-4-硝基环己基-1-烯，涉及两步过程，即各自糖侧链的碱催化（NaOMe）脱乙酰化作用，以及随后的氧化裂解（NaIO 4）。当1a或1b与马来酸二甲酯，富马酸二甲酯或反式甲酯反应时用DBU（代替TMG）作为催化剂进行-4-氧戊烯酸酯，就地消除了亚硝酸。

  DOI：

  10.1016/s0957-4166(02)00416-0

文献信息

• Preparation of enantiomerically pure 4-alkyl-5-formyl-4-nitrocyclohex-1-enes from 5-glyco-4-nitrocyclohex-1-enes
  作者：R. Ballini、G. Bosica、M.V. Gil、E. Román、J.A. Serrano

  DOI：10.1016/s0957-4166(02)00416-0

  日期：2002.8

  electron-deficient alkenes yielded, in all cases, adducts in which the sugar side-chain and the added group on C-4 of the cyclohexene ring showed a trans-relationship. Furthermore, some of the adducts have been used to prepare enantiomerically pure 4-alkyl-5-formyl-4-nitrocyclohex-1-enes by a two-step process involving base-catalyzed (NaOMe) deacetylation of their respective sugar side-chains and subsequent

  在所有情况下，碱催化（TMG，DBU或TEA）在5-glyco-4-nitrocyclohex-1-enes 1a或1b与许多单或α，β-di取代的缺电子烯烃之间的不对称Michael反应，加合物，其中所述糖侧链和添加的组上C-4的环己烯环的呈反式-relationship。此外，一些加合物已用于通过两步法制备对映体纯的4-烷基-5-甲酰基-4-硝基环己基-1-烯，涉及两步过程，即各自糖侧链的碱催化（NaOMe）脱乙酰化作用，以及随后的氧化裂解（NaIO 4）。当1a或1b与马来酸二甲酯，富马酸二甲酯或反式甲酯反应时用DBU（代替TMG）作为催化剂进行-4-氧戊烯酸酯，就地消除了亚硝酸。
• Nitrous acid elimination from 4-alkyl-5-formyl-4-nitrocyclohex-1-enes: synthesis of mono and bicyclic benzene and dihydrobenzene derivatives
  作者：M.V Gil、E Román、J.A Serrano

  DOI：10.1016/s0040-4039(01)00828-0

  日期：2001.7

  Elimination of nitrous acid from 4-alkyl-5-formyl-4-nitrocyclohex-1-enes, by treatment with silica gel or potassium carbonate, is described. Whereas in the former case the product consisted in a mixture of the starting material, 2-alkyl-4,5dimethylcyclohexa-1,4-diene-1-carbaldehyde and 2-alkyl-4,5-dimethylbenzaldehyde, reaction with potassium carbonate at 60 degreesC yielded exclusively aromatic compounds. Furthermore, when a ketone Function was present in the gamma -position of the ail;yl chain at C-4, the alkaline medium promoted an intramolecular. aldol condensation, bring obtained bicyclic products. PM3 calculations have been made to justify the result of the cyclization. (C) 2001 Elsevier Science Ltd. All rights reserved.