3-Hydroxy-1-(2.6.6-trimethyl-1.3-cyclohexadien-1-yl)-1-butanon | 41436-47-9

• 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: 3-Hydroxy-1-(2.6.6-trimethyl-1.3-cyclohexadien-1-yl)-1-butanon
• 英文别名: 3-Hydroxy-1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)butan-1-one
• CAS: 41436-47-9
• 化学式: C₁₃H₂₀O₂
• 分子量: 208.301
• InChiKey: JZYGEEGHUZSFEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  r-4-Acetyl-4-brom-t-3,5,5-trimethylcyclohexen 在 乙基溴化镁 、 lithium carbonate 、 lithium fluoride 、 N-甲基苯胺 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 生成 3-Hydroxy-1-(2.6.6-trimethyl-1.3-cyclohexadien-1-yl)-1-butanon
  参考文献：
  名称：

  Ayyar,K.S. et al., Journal of the Chemical Society. Perkin transactions I, 1975, p. 1727 - 1736

  摘要：

  DOI：

文献信息

• Rationalizing the Formation of Damascenone: Synthesis and Hydrolysis of Damascenone Precursors and Their Analogues, in both Aglycone and Glycoconjugate Forms
  作者：Merran A. Daniel、Carolyn J. Puglisi、Dimitra L. Capone、Gordon M. Elsey、Mark A. Sefton

  DOI：10.1021/jf8018134

  日期：2008.10.8

  megastigma-4,6,7-trien-9-ol (7) and megastigma-6,7-dien-9-ol (8) were synthesized. No 1,3-transposition of oxygen to form analogues of damascenone was observed when 7 and 8 were subjected to mild acidic conditions. Such transposition takes place only with highly conjugated acetylenic precursors such as 6 or tertiary allenic alcohols such as 2. The placement of glucose at C-3 of 5 and at C-9 of 6 gave the

  megastigma-4,6,7-trien-3,9-diol（5）和megastigma-3,4-dien-7-yn-9-ol（6）在pH 3.0和3.2的乙醇水溶液中储存仅在室温下为damascenone（1）和damascenone加合物。二醇（5）在pH 3.0和pH 3.2下分别具有32和48小时转化的半衰期。在相同的pH值下，炔醇（6）的半衰期分别为40和65 h。为了研究5和先前研究的烯丙三醇2中C-9羟基官能团的反应性，两种模型化合物megastigma-4,6,7-trien-9-ol（7）和megastigma-6,7合成了-dien-9-ol（8）。当将7和8置于温和的酸性条件下时，未观察到氧的1,3-易位形成大马mas酮的类似物。仅用高度共轭的炔属前体（如6）或叔烯丙醇（如2）进行这种转座。将葡萄糖分别置于C-3为5和C-9为6时分别得到糖苷9和10。这种葡糖缀合的
• Fate of Damascenone in Wine:  The Role of SO₂
  作者：Merran A. Daniel、Gordon M. Elsey、Dimitra L. Capone、Michael V. Perkins、Mark A. Sefton

  DOI：10.1021/jf048582h

  日期：2004.12.1

  Damascenone has been shown to undergo reaction with common wine components. Following the action of acid and heat alone, two bicyclic compounds, 4,9,9-trimethyl-8-methylenebicyclo[3.3.1]non-6-en-2-one (2) and 4,4,9-trimethyl-8-methylenebicyclo[3.3.1] non-6-en-2-one (3), were isolated. However, this conversion takes place only very slowly, if at all, under milder conditions (45 degrees C). When treated

  已证明大马烯酮会与常见的葡萄酒成分发生反应。仅在酸和热作用下，两个双环化合物即4,9,9-三甲基-8-亚甲基双环[3.3.1] non-6-en-2-one（2）和4,4,9-三甲基-分离出8-亚甲基双环[3.3.1]非6-en-2-one（3）。但是，这种转换仅在非常温和的条件下（45摄氏度）才非常缓慢（如果有的话）进行。当在pH 3.0和5.5的条件下用各种亲核试剂处理时，除了在pH 5.5时添加半胱氨酸和2-巯基乙醇（约40％和约30％）外，缓冲水溶液中的大马烯酮浓度会少量降低（10-20％），分别）和SO2（pH 3.0时> 90％; pH 5.5时100％）。制备了来自该最后组合的加合物，其显示为大马烯酮的C9磺酸衍生物。
• Process for preparing
  申请人：International Flavors & Fragrances Inc.

  公开号：US04157350A1

  公开（公告）日：1979-06-05

  Described is a process for preparing an equilibrium mixture containing 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-1,3-butanedione and its enol, which equilibrium mixture contains compounds having the structures: ##STR1## which process involves first reacting a methyl magnesium halide with 1-acetyl-2,6,6-trimethyl-1,3-cyclohexadiene to form a first organometallic compound; reacting the first organometallic compound with an acetyl halide to form a second organometallic compound, a novel intermediate; and then reacting said second organometallic compound with a hydrolyzing agent such as aqueous acid to form said equilibrium mixture.

  本发明涉及一种制备1-(2,6,6-三甲基-1,3-环己二烯-1-基)-1,3-丁二酮及其烯醇的平衡混合物的过程，该平衡混合物含有以下结构的化合物：##STR1## 该过程首先涉及将甲基镁卤和1-乙酰基-2,6,6-三甲基-1,3-环己二烯反应，形成第一有机金属化合物；将第一有机金属化合物与乙酰卤反应，形成第二有机金属化合物，一种新的中间体；然后将所述第二有机金属化合物与水解剂（如水酸）反应，形成所述平衡混合物。
• 1-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-1,3-butanedione and
  申请人：International Flavors & Fragrances Inc.

  公开号：US04157351A1

  公开（公告）日：1979-06-05

  Processes and compositions are described for the use in tobacco flavor and aroma and perfume aroma augmenting, modifying, enhancing and imparting compositions and as tobacco, perfume, cologne and perfumed article aroma imparting materials of 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-1,3-butanedione which has the structure: ##STR1## which also, in its enolate form, has the structure: ##STR2##

  描述了用于烟草风味和香气以及香水香气增强、修改、增强和赋予组合物的过程和组成，以及作为烟草、香水、古龙水和香水物品香气赋予材料的1-(2,6,6-三甲基-1,3-环己二烯-1-基)-1,3-丁二酮，其结构为：##STR1##，在其烯醇酸盐形式中也具有以下结构：##STR2##
• Compounds for a controlled release of active molecules
  申请人：——

  公开号：US20040220074A1

  公开（公告）日：2004-11-04

  The present invention relates to the field of perfumery. More particularly, it concerns compounds comprising at least one &bgr;-oxy or &bgr;-thio carbonyl moiety capable of liberating a perfuming molecule such as, for example, an &agr;,&bgr;-unsaturated ketone, aldehyde or carboxylic ester. The present invention concerns also the use of the compounds in perfumery as well as the perfuming compositions or perfumed articles comprising the invention's compounds.

  本发明涉及香料领域。更具体地，它涉及包含至少一个β-氧或β-硫酰基团的化合物，该化合物能够释放出一种香料分子，例如α，β-不饱和酮，醛或羧酸酯。本发明还涉及将该化合物用于香料以及包含本发明化合物的香料组合物或带香物品。