ethyl 2,4-dimethyl-4-pentenoate | 90646-75-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 2,4-dimethyl-4-pentenoate
• 英文别名: ethyl 2,4-dimethylpent-4-enoate；2,4-Dimethyl-penten-(4)-saeure-(1)-ethylester
• CAS: 90646-75-6
• 化学式: C₉H₁₆O₂
• 分子量: 156.225
• InChiKey: XNSTVAFSRSRYQC-UHFFFAOYSA-N

物化性质

• 沸点：
  165.3±9.0 °C(Predicted)
• 密度：
  0.888±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl 2,4-dimethyl-4-pentenoate 在 palladium on activated charcoal 吡啶 、 lithium aluminium tetrahydride 、 氢气 、 magnesium 、 lithium bromide 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 6.0h， 生成 4,6-二甲基-1-庚醇
  参考文献：
  名称：

  Neutral compounds from male castoreum of North American beaver,Castor canadensis

  摘要：

  North American beavers (Casio, canadensis) mark their territories with castoreum, the strong-smelling paste in their castor sacs. In their own territories, beavers respond with scent marking to experimental scent marks that consist of strange castoreum (or selected components). In part, the unique odor of castoreum is due to large amounts of phenolic compounds rind neutral compounds. Purifed neutral compounds were analyzed by GC, GC-MS, and NMR; identities of the neutral compounds were confirmed by comparing the properties of authentic compounds with those of the isolated compounds. We identified 13 neutral compounds that had not been reported before for castoreum. Most of these are oxygen-containing monoterpenes, Of the nine neutral compounds reported by Lederer (1949), only three are confirmed in our analysis; the other six neutral compounds are either absent or are not volatile enough to be detected by our methods. Eight compounds-6-methyl-1-heptanol, 4,6-dimethyl-1-heptanol, isopinocamphone, pinocamphone, two linalool oxides, and their acetates-were synthesized for structure identification and bioassays.

  DOI：

  10.1007/bf02033674
• 作为产物：
  描述：

  原丙酸三乙酯 、 2-甲基-2-丙烯-1-醇 在 丙酸 作用下， 以93%的产率得到ethyl 2,4-dimethyl-4-pentenoate
  参考文献：
  名称：

  Neutral compounds from male castoreum of North American beaver,Castor canadensis

  摘要：

  North American beavers (Casio, canadensis) mark their territories with castoreum, the strong-smelling paste in their castor sacs. In their own territories, beavers respond with scent marking to experimental scent marks that consist of strange castoreum (or selected components). In part, the unique odor of castoreum is due to large amounts of phenolic compounds rind neutral compounds. Purifed neutral compounds were analyzed by GC, GC-MS, and NMR; identities of the neutral compounds were confirmed by comparing the properties of authentic compounds with those of the isolated compounds. We identified 13 neutral compounds that had not been reported before for castoreum. Most of these are oxygen-containing monoterpenes, Of the nine neutral compounds reported by Lederer (1949), only three are confirmed in our analysis; the other six neutral compounds are either absent or are not volatile enough to be detected by our methods. Eight compounds-6-methyl-1-heptanol, 4,6-dimethyl-1-heptanol, isopinocamphone, pinocamphone, two linalool oxides, and their acetates-were synthesized for structure identification and bioassays.

  DOI：

  10.1007/bf02033674

文献信息

• Process for the preparation of novel aromatic compounds
  申请人：Firmenich SA

  公开号：US05442124A1

  公开（公告）日：1995-08-15

  A process for the preparation of novel compounds with a tetraline-type structure, which are useful as perfuming ingredients, is described.

  描述了一种制备具有四氢萘型结构的新化合物的方法，这些化合物可用作香料成分。
• Au- and Pt-Catalyzed Cycloisomerizations of 1,5-Enynes to Cyclohexadienes with a Broad Alkyne Scope
  作者：Jianwei Sun、Matthew P. Conley、Liming Zhang、Sergey A. Kozmin

  DOI：10.1021/ja063384n

  日期：2006.8.1

  Elucidation of this unusual reaction mechanism enabled us, in turn, to significantly expand the scope of the cycloisomerization by incorporation of a quaternary center at the C(3) position of the enyne. Indeed, we established that PtCl(2) (5 mol %) efficiently catalyzed the cycloisomerizations of 1,5-enynes containing terminal, internal, and arene-conjugated alkynes. Since a variety of 1,5-enynes are readily

  我们描述了金和铂催化的 1,5-烯炔环异构化的发展。这种催化过程显示出广泛的炔烃范围，并提供了一系列高度官能化的 1,4- 和 1,3- 环己二烯。在 1-siloxy-1-yne-5-enes 的情况下，反应在环境温度下被 AuCl（1 mol%）有效催化，得到甲硅烷氧基环己二烯或相应的 1,2- 和 1,3-环己烯酮。原脱甲硅烷化。我们建议该反应通过涉及一系列 1,2-烷基转移的新机制进行。反过来，阐明这种不寻常的反应机制使我们能够通过在烯炔的 C(3) 位置加入季铵中心来显着扩大环异构化的范围。事实上，我们确定 PtCl(2) (5 mol %) 有效地催化了 1 的环异构化，包含末端、内部和芳烃共轭炔的 5-烯炔。由于各种 1,5-烯炔很容易获得，环异构化为许多后续合成应用提供了广泛的高取代环己二烯的快速方法。
• 1,2-Migrations in free radicals related to coenzyme B12-dependent rearrangements
  作者：Susan. Wollowitz、Jack. Halpern

  DOI：10.1021/ja00218a020

  日期：1988.5

  Les radicaux libres XC(CH 3 )(COOR)CH 2 • , ou X=C(=0)Me, C(=O)SEt, C(=0)OEt, C(=CH 2 )Me, et C 6 H 5 , sont generes par reaction des bromures correspondants avec (n-bu) 3 SnH. Etude de la reaction de migration-1,2 de X pour former les radicaux • C(CH 3 )(COOR)(CH 2 X)

  Les radicaux libres XC(CH 3 )(COOR)CH 2 • , ou X=C(=0)Me, C(=O)SEt, C(=0)OEt, C(=CH 2 )Me, et C 6 H 5 ，sont generes par reaction des bromures对应物avec (n-bu) 3 SnH。Etude de la reaction de migration-1,2 de X pour form les radicaux • C(CH 3 )(COOR)(CH 2 X)
• Aromatic compounds, a process for preparation thereof and use of same as
  申请人：Firmenich S.A.

  公开号：US05162588A1

  公开（公告）日：1992-11-10

  Compound of formula ##STR1## wherein a) indexes m and n are identical and stand each for an integer number equal to zero, symbols R.sup.1 and R.sup.2 are identical and represent each a hydrogen atom, or are different and represent each a hydrogen atom or a methyl radical, symbols R.sup.5 and R.sup.8 stand each for a methyl radical, symbols R.sup.6 and R.sup.7 can be identical or different and designate each a hydrogen atom or a methyl radical and, either symbol R.sup.4 represents a methyl radical and symbol R.sup.3 stands for a hydrogen atom or a methyl radical, or symbols R.sup.3 and R.sup.4 represent each a methylene radical belonging to a ring such as indicated by the dotted line, with the proviso that the following combinations are excluded: 1. R.sup.1 =R.sup.2 =R.sup.3 =R.sup.6 =R.sup.7 =H, or 2. R.sup.1 =R.sup.2 =R.sup.3 =H and R.sup.6 or R.sup.7 =CH.sub.3, or 3. R.sup.2 =CH.sub.3 and R.sup.3 =R.sup.6 =R.sup.7 =H, or 4. R.sup.2 =CH.sub.3 and R.sup.3 =H and R.sup.6 or R.sup.7 =CH.sub.3, or 5. R.sup.1 =R.sup.3 =CH.sub.3, or 6. R.sup.3 =R.sup.4 =CH.sub.2 and R.sup.2 or R.sup.7 =CH.sub.3 ; or wherein b) indexes m and n are different and define each an integer number equal to 0 or 1, symbol R.sup.2 stands for a hydrogen atom or a methyl radical, symbols R.sup.1 and R.sup.3 designate each a hydrogen atom, symbol R.sup.4 represents a methyl radical and, either symbols R.sup.5 and R.sup.6 are identical (n=1) and represent each a methylene radical belonging to a ring such as indicated by the dotted line, R.sup.7 representing a hydrogen atom and R.sup.8 a methyl radical, or symbol R.sup.5 stands for a methyl radical and symbol R.sup.6 for a hydrogen atom, R.sup.7 and R.sup.8 being then identical (m=1) and designating each a methylene radical belonging to a ring such as indicated by the dotted line; or any mixture of two or more structural isomers of formula (I). Compounds (I) develop odor notes of the musky type and can therefore be used as active ingredients in perfuming compositions and perfumed articles of varied nature. A process for the preparation of compounds (I) is described.

  化合物的式子为##STR1##其中a）索引m和n相同，分别代表等于零的整数，符号R.sup.1和R.sup.2相同，分别代表氢原子，或者不同，分别代表氢原子或甲基基团，符号R.sup.5和R.sup.8分别代表甲基基团，符号R.sup.6和R.sup.7可以相同也可以不同，分别指代氢原子或甲基基团，要么符号R.sup.4代表甲基基团，符号R.sup.3代表氢原子或甲基基团，要么符号R.sup.3和R.sup.4分别代表属于环的亚甲基基团，如虚线所示，但以下组合被排除：1. R.sup.1 = R.sup.2 = R.sup.3 = R.sup.6 = R.sup.7 = H，或2. R.sup.1 = R.sup.2 = R.sup.3 = H且R.sup.6或R.sup.7 = CH.sub.3，或3. R.sup.2 = CH.sub.3且R.sup.3 = R.sup.6 = R.sup.7 = H，或4. R.sup.2 = CH.sub.3且R.sup.3 = H且R.sup.6或R.sup.7 = CH.sub.3，或5. R.sup.1 = R.sup.3 = CH.sub.3，或6. R.sup.3 = R.sup.4 = CH.sub.2且R.sup.2或R.sup.7 = CH.sub.3；或b）索引m和n不同，分别定义为等于0或1的整数，符号R.sup.2代表氢原子或甲基基团，符号R.sup.1和R.sup.3各自指代氢原子，符号R.sup.4代表甲基基团，要么符号R.sup.5和R.sup.6相同（n=1）且分别代表属于环的亚甲基基团，如虚线所示，R.sup.7代表氢原子，R.sup.8代表甲基基团，要么符号R.sup.5代表甲基基团，符号R.sup.6代表氢原子，R.sup.7和R.sup.8则相同（m=1），分别指代属于环的亚甲基基团，如虚线所示；或者化合物（I）的两种或更多结构异构体的任意混合物。化合物（I）具有麝香类型的气味，因此可以用作调香组合物和各种性质的香水产品中的活性成分。描述了一种制备化合物（I）的方法。
• Polycyclic Musks. I. Acyl- and Dinitropolyalkyltetralin Derivatives
  作者：T. F. Wood、W. M. Easter、M. S. Carpenter、J. Angiolini

  DOI：10.1021/jo01044a022

  日期：1963.9