3-methoxycarbonyl-6,10-dimethyl-E,E-5,9-undecadien-2-one | 51933-45-0

• 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-methoxycarbonyl-6,10-dimethyl-E,E-5,9-undecadien-2-one
• 英文别名: methyl 2-geranyl-3-oxobutanonate；Methyl-geranylacetoacetat；methyl (4E)-2-acetyl-5,9-dimethyl-4,8-decadienoate；methyl (4E)-2-acetyl-5,9-dimethyldeca-4,8-dienoate
• CAS: 51933-45-0
• 化学式: C₁₅H₂₄O₃
• 分子量: 252.354
• InChiKey: BSTPZJQNOMFGJU-FMIVXFBMSA-N

物化性质

• 沸点：
  353.5±42.0 °C(Predicted)
• 密度：
  0.956±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-methoxycarbonyl-6,10-dimethyl-E,E-5,9-undecadien-2-one 在 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 以65%的产率得到香叶基丙酮
  参考文献：
  名称：

  Epoxides from Myrcene: New Versatile Tools for the Synthesis of Functionalized Acyclic Terpenoids

  摘要：

  Mono-epoxides prepared from myrcene, were used as synthetic intermediates to obtain citral, linalool, geranylacetone and pseudo-ionone.

  DOI：

  10.1080/00397919908086005
• 作为产物：
  描述：

  Linalool-phenylurethan 、 乙酰乙酸甲酯 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以86%的产率得到3-methoxycarbonyl-6,10-dimethyl-E,E-5,9-undecadien-2-one
  参考文献：
  名称：

  Epoxides from Myrcene: New Versatile Tools for the Synthesis of Functionalized Acyclic Terpenoids

  摘要：

  Mono-epoxides prepared from myrcene, were used as synthetic intermediates to obtain citral, linalool, geranylacetone and pseudo-ionone.

  DOI：

  10.1080/00397919908086005

文献信息

• Efficient Lewis Acid Mediated Epoxyolefin Cyclizations with Pyrones as Terminators in Liquid SO₂ as a Solvent
  作者：Uwe Beifuss、Dietmar Schmidt、Heiko Leutbecher、Jürgen Conrad、Iris Klaiber、Sabine Mika、Gerhard Greiner

  DOI：10.1055/s-2007-984506

  日期：2007.7

  Lewis acids like BF3·OEt2, TiCl4, ZnCl2·OEt2, ZnI2, and InCl3 in liquid SO2 as a solvent at low temperatures have been found to be highly efficient in epoxyolefin cyclizations with pyrones as terminators.

  人们发现，路易斯酸（如 BF3·OEt2、TiCl4、ZnCl2·OEt2、ZnI2 和 InCl3）在低温下以液态 SO2 为溶剂，在以吡喃酮为终止剂的环氧烯烃环化中非常有效。
• An integrated approach to the synthesis of contiguously substituted xanthopurpurins, pachybasins and purpurins.
  作者：Brigitte Caron、Paul Brassard

  DOI：10.1016/s0040-4020(01)80322-7

  日期：1993.1

  Alkylation, hydroxyalkylation and acylation of 3-methyl-, 3-methoxy- and 3,4-dimethoxycrotonates can be induced to occur exclusively in the alpha-Position. Conversion of the products to dienes then provides, through cycloaddition, a wide variety of substitution patterns. This approach is illustrated by simplified syntheses of a number of naturally occurring quinones and confirms the structures proposed for vismiaquinone C, 7-geranylemodin, cinnalutein, 4,5-dihydroxydigitolutein, 2-hydroxyislandicin 1-methyl ether and calyculatone 1-methyl ether.
• Atom economy. A simple Pd catalyzed addition of pronucleophiles with dienes
  作者：Barry M. Trost、Lin Zhi

  DOI：10.1016/s0040-4039(00)74154-2

  日期：1992.3

  Replacing allylic alkylations involving allylic halides, carboxylates, etc. by the simple addition of pronucleophiles to dienes enhances efficiency of use of raw materials and reduces generation of stochiometric by-products.
• A one-pot preparation of α-halo-carbonyl and α-halo-sulfonyl compounds by halo-deacylation
  作者：G. Mignani、D. Morel、F. Grass

  DOI：10.1016/s0040-4039(00)96765-0

  日期：1987.1
• Internal nucleophilic termination in mercuric ion initiated diene cyclizations
  作者：Thomas R. Hoye、Andrew J. Caruso、Mark J. Kurth

  DOI：10.1021/jo00330a037

  日期：1981.8