6-allyl-3-methyl-cyclohex-2-enone | 84695-64-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-allyl-3-methyl-cyclohex-2-enone
• 英文别名: 3-Methyl-6-prop-2-enylcyclohex-2-en-1-one
• CAS: 84695-64-7
• 化学式: C₁₀H₁₄O
• 分子量: 150.221
• InChiKey: GBPSCEIJTAVPBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-allyl-3-methyl-cyclohex-2-enone 在 吡啶 、 lithium aluminium tetrahydride 、 臭氧 、 溶剂黄146 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 6.5h， 生成 cis-3-methyl-6-(2-((triethylsilyl)oxy)ethyl)-2-cyclohexenol
  参考文献：
  名称：

  Alkoxides as nucleophiles in (.pi.-allyl)palladium chemistry. Synthetic and mechanistic studies

  摘要：

  DOI：

  10.1021/ja00345a050
• 作为产物：
  描述：

  tert-butyl 2-acetyl-4-pentenoate 在 sodium ethanolate 、 对甲苯磺酸 作用下， 生成 6-allyl-3-methyl-cyclohex-2-enone
  参考文献：
  名称：

  Lawesson,S.-O. et al., Recueil des Travaux Chimiques des Pays-Bas, 1964, vol. 83, p. 464 - 468

  摘要：

  DOI：

文献信息

• Organomanganese (II) reagents XVI1: copper-catalyzed 1,4-addition of organomanganese chlorides to conjugated enones
  作者：Gérard Cahiez、Mouad Alami

  DOI：10.1016/s0040-4039(00)99434-6

  日期：1989.1

  Copper-catalyzed conjugate addition of organomanganese chlorides to conjugated enones in THF, at 0°C, leads to the 1,4 addition products in high yields. The scope of the reaction is very large and the results are generally better than those obtained from organomagnesium compounds in the presence of a copper salt as well as from organocopper or cuprate reagents. Furthermore organomanganese chlorides are indisputably

  在0℃下，铜催化的有机锰氯化物在THF中的共轭烯酮的共轭加成反应，可高产率地产生1,4加成产物。该反应的范围非常大，其结果通常比在铜盐以及有机铜或铜酸盐试剂存在下从有机镁化合物获得的结果更好。此外，有机锰氯化物无疑比后者更便宜，更稳定。
• Mn(III)-mediated radical CC bond formation: regioselective α′-allylation of α,β-unsaturated ketones
  作者：Cihangir Tanyeli、Devrim Özdemirhan

  DOI：10.1016/s0040-4039(02)00726-8

  日期：2002.5

  Mn(OAc)3-mediated regioselective α′-allylation of α,β-unsaturated enones is described. α′-Allyl α,β-unsaturated enones are obtained through a radical process in good yields.

  描述了Mn（OAc）3介导的α，β-不饱和烯酮的区域选择性α'-烯丙基化。通过自由基过程以高收率获得α′-烯丙基α，β-不饱和烯酮。
• Mn(III)-based C–C bond formation: regioselective α′-allylation of various α,β-unsaturated, α and β-alkoxy α,β-unsaturated ketones
  作者：Cihangir Tanyeli、Devrim Özdemirhan

  DOI：10.1016/j.tet.2005.06.031

  日期：2005.8

  The Manganese(III) -based regioselective alpha'-keto radical generation of unsaturated ketones is a versatile synthetic procedure with broad applicability. The generated alpha'-keto radical slowly creates a metal enolate in a solvent at reflux. The resultant metal enolate affords the corresponding alpha'-allylated alpha,beta-unsaturated ketones in good yields. This method is the first example of the metal mediated regioselective alpha'-allylation of alpha,beta-unsaturated ketones. The ketones that have alpha or beta-alkoxy groups also work efficiently. (c) 2005 Elsevier Ltd. All rights reserved.
• Nicolaou, K. C.; Stepan, Antonia F.; Lister, Troy, Journal of the American Chemical Society, 2008, vol. 130, p. 13110 - 13119
  作者：Nicolaou, K. C.、Stepan, Antonia F.、Lister, Troy、Li, Ang、Montero, Ana、et al.

  DOI：——

  日期：——
• Feasibility of an immunoassay for mevalonolactone
  作者：Thomas A. Spencer、Dawn S. Clark、Gary A. Johnson、Sandra K. Erickson、Linda K. Curtiss

  DOI：10.1016/s0968-0896(97)00032-1

  日期：1997.5

  Mevalonic acid is a key intermediate in a broad spectrum of cellular biological processes and their regulation. Availability of a rapid, sensitive and accurate method for its assay would be highly useful. Therefore, the feasibility of developing an immunoassay for mevalonic acid in biological samples was explored. The strategy employed was to synthesize several racemic haptens structurally resembling R-mevalonolactone, the cyclic form of mevalonic acid present at lower pH and presumed to be more antigenic. Two of these haptens were coupled to keyhole limpet hemocyanin, and the resulting conjugates were used successfully to generate antibodies in rabbits. The first antiserum bound to R,S-mevalonolactone much more effectively at pH 4.0 than at pH 6.0, consistent with the structural resemblance of the haptens to the lactone form. This antiserum also bound the free hapten from which it was generated and two others of different structure with comparable effectiveness, and slightly better than it bound R,S-mevalonolactone at pH 4.0. Similar results were obtained with the antiserum to the second hapten. The binding of either antiserum to the natural enantiomer, R-mevalonolactone, was 20 times weaker than to R,S-mevalonolactone, suggesting that the nonbiological enantiomer was more antigenic. Nevertheless, the results demonstrate that an immunochemical approach to accurate quantitation of mevalonic acid in biological samples is feasible. (C) 1997 Elsevier Science Ltd.