isosylveterpinolene | 25946-29-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: isosylveterpinolene
• 英文别名: m-Mentha-1(6),3(8)-dien; Isosylveterpinolen；6,3(8)-m-Menthadien; Silvesterpinolen；m-Menthadien-(6,3(8))；5-Isosylveterpinolene；1-methyl-5-propan-2-ylidenecyclohexene
• CAS: 25946-29-6
• 化学式: C₁₀H₁₆
• 分子量: 136.237
• InChiKey: WPOQYXKDKVBMSB-UHFFFAOYSA-N

物化性质

• 沸点：
  182.0±15.0 °C(Predicted)
• 密度：
  0.853±0.06 g/cm3(Predicted)
• 保留指数：
  1116

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  isosylveterpinolene 在 溴 作用下， 以 乙醚 、 戊醇 为溶剂， 生成 1,3,6,8-Tetrabrom-m-menthan
  参考文献：
  名称：

  Muraleedharan,N.V.; Verghese,J., Journal of the Indian Chemical Society, 1972, vol. 49, p. 289 - 292

  摘要：

  DOI：
• 作为产物：
  描述：

  3-甲基环己-3-烯-1-酮 在 正丁基锂 、 N,N-二甲基甲酰胺二甲基缩醛 、 二异丙胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 isosylveterpinolene
  参考文献：
  名称：

  Identification ofm-Mentha-3(8),6-diene (Isosylveterpinolene) in Black Pepper Oil

  摘要：

  m-Mentha-3(8),6-diene (= isosylveterpinolene; 5),which has not been found in nature before, was shown by GC/MS analysis and co-injection with a synthetic sample to be present to the extent of 0.12-0.17% in black and green pepper oil. The synthetic reference 5 was prepared by deconjugation of 3-methylcyclohex-2-en-1-one (1), subsequent alkylation with lithium 2-lithio-2-methylpropanoate, and decarboxylative dehydration of the resulting hydroxycarboxylic acid 3 employing dimethylformamide dimethyl acetal. On polar GC columns, 5 was eluted between p-cymene and terpinolene, and was characterized by an MS similar to that of terpinolene, but with the fragment mit 121 (59, [M - Me](+)) being less intense than that of the molecular ion at mit 136 (67, M+). Since m-mentha-3(8),6-diene was also found to the extent of 0.24% in the headspace of ground black peppercorns, it can be considered to be of genuine natural origin, and thus is the first established example of a naturally occurring m-menthadiene.

  DOI：

  10.1002/(sici)1522-2675(19990113)82:1<53::aid-hlca53>3.0.co;2-7

文献信息

• Organocatalytic Multicomponent α-Methylenation/Diels–Alder Reactions: A Versatile Route to Substituted Cyclohexenecarbaldehyde Derivatives
  作者：Yue Zou、Quanrui Wang、Andreas Goeke

  DOI：10.1002/chem.200800145

  日期：2008.6.9

  describes the design and optimization of an effective organocatalytic three-component domino alpha-methylenation/Diels-Alder reaction to produce vinyl-substituted cyclohexenecarboxaldehydes in a highly regioselective fashion. In these one-pot transformations, 2-formyl-1,3-butadienes (4) were prepared in situ from alpha,beta-unsaturated aldehydes and formalin and were subsequently trapped with a variety

  本文介绍了一种有效的有机催化三组分多米诺骨牌α-甲基化/ Diels-Alder反应的设计和优化，该反应以高度区域选择性的方式生产乙烯基取代的环己烯甲醛。在这些一锅转化中，由α，β-不饱和醛和福尔马林原位制备2-甲酰基-1，3-丁二烯（4），随后被各种丁1，3-二烯捕获。反应的结果取决于二烯的电子性质。1-乙烯基环己烯甲醛6是通过使用富含无环电子的二烯形成的，而最初形成的4与环戊二烯的环加合物进行了Cope重排，导致形成了四氢3 H-茚5醛7。这些反应涉及的机制是从实验结果推论得出的。此外，该方法还扩展到二氢呋喃和二氢吡喃的一锅多米诺甲基化/ Diels-Alder反应，生成螺环内酯22。在这些反应中，不稳定的中间体羟乙基和羟丙基丙烯醛表现为二烯亲和性，与具有良好二烯的二烯进行环加成反应产率和选择性。通过使用这些有机催化多米诺法作为多样性导向的合成方法，产生了各种各样的官能化的1-乙烯基环
• Muraleedharan,N.V.; Verghese,J., Journal of the Indian Chemical Society, 1972, vol. 49, p. 289 - 292
  作者：Muraleedharan,N.V.、Verghese,J.

  DOI：——

  日期：——
• Identification ofm-Mentha-3(8),6-diene (Isosylveterpinolene) in Black Pepper Oil
  作者：Cornelius Nussbaumer、Riccardo Cadalbert、Philip Kraft

  DOI：10.1002/(sici)1522-2675(19990113)82:1<53::aid-hlca53>3.0.co;2-7

  日期：1999.1.13

  m-Mentha-3(8),6-diene (= isosylveterpinolene; 5),which has not been found in nature before, was shown by GC/MS analysis and co-injection with a synthetic sample to be present to the extent of 0.12-0.17% in black and green pepper oil. The synthetic reference 5 was prepared by deconjugation of 3-methylcyclohex-2-en-1-one (1), subsequent alkylation with lithium 2-lithio-2-methylpropanoate, and decarboxylative dehydration of the resulting hydroxycarboxylic acid 3 employing dimethylformamide dimethyl acetal. On polar GC columns, 5 was eluted between p-cymene and terpinolene, and was characterized by an MS similar to that of terpinolene, but with the fragment mit 121 (59, [M - Me](+)) being less intense than that of the molecular ion at mit 136 (67, M+). Since m-mentha-3(8),6-diene was also found to the extent of 0.24% in the headspace of ground black peppercorns, it can be considered to be of genuine natural origin, and thus is the first established example of a naturally occurring m-menthadiene.