E-6-nonen-2-one | 56889-98-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: E-6-nonen-2-one
• 英文别名: (E)-non-6-en-2-one；6E-Nonen-2-one
• CAS: 56889-98-6
• 化学式: C₉H₁₆O
• 分子量: 140.225
• InChiKey: TVHAWOPAFXXIQM-SNAWJCMRSA-N

物化性质

• 沸点：
  46-48 °C(Press: 1.5 Torr)
• 密度：
  0.835±0.06 g/cm3(Predicted)
• LogP：
  2.660 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  10
• 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：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  E-6-nonen-2-one 在 四乙基对甲苯磺酸铵 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 生成 cis-1-Methyl-2-n-propylcyclopentanol
  参考文献：
  名称：

  Electroorganic chemistry. 31. Reductive cyclization of nonconjugated olefinic ketones to cyclic tertiary alcohols

  摘要：

  DOI：

  10.1021/ja00470a031
• 作为产物：
  描述：

  反式-3-己烯-1-醇 在 copper(l) iodide 、 重铬酸吡啶 、 4 A molecular sieve 、 溴 、 magnesium 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 E-6-nonen-2-one
  参考文献：
  名称：

  Pheromone specificity inEriocrania semipurpurella (Stephens) andE. sangii (Wood) (Lepidoptera: Eriocraniidae) based on chirality of semiochemicals

  摘要：

  The fifth abdominal segment of female Eriocrania semipurpurella (Stephens) and E. sangii (Wood) contains a pair of exocrine glands. Hexane extracts of this segment were prepared from both species and analyzed by gas chromatography with simultaneous flame ionization and electroantennographic detection (EAD). For both species, the EAD active peaks were identified as nonan-2-one, (Z)-6-nonen-2-one, and (Z)-6-nonen-2-ol by means of mass spectrometry and comparison of retention indices with those of synthetic standards. Enantiomeric separation of chiral alcohols from the female extracts was achieved by gas chromatographic analysis on a cyclodextrin column. In E. semipurpurella, a mixture of (2S,6Z)-nonen-2-ol and (2R,6Z)-nonen-2-ol (2:1) was found, whereas in E. sangii (2S,6Z)-nonen-2-ol was the predominant enantiomer and only traces of the R enantiomer were indicated by the antennal response. In held tests, a blend of the three compounds was not attractive to conspecific males. A subtractive assay showed that the alcohol in various enantiomeric mixtures was the only attractive compound, whereas addition of (Z)-6-nonen-2-one to the alcohol completely inhibited the attraction of both species. A trapping experiment including a wide range of ratios between the R and S enantiomers showed that baits containing 95-100% of the S enantiomer were attractive to male E. sangii, whereas males of E. semipurpurella were attracted to all tested ratios of the enantiomers. However, the response profiles of male E. semipurpurella differed between populations from southern Sweden, south Finland, and the Kola Peninsula in Russia. In south Sweden males were maximally attracted to a racemic mixture of the alcohols. At the Kola Peninsula E. semipurpurella was attracted to baits containing 95-100% of the R enantiomer. In south Finland all tested ratios between 0 and 100% R enantiomer trapped E. semipurpurella, but the trap catches appeared to be bimodally distributed with peaks around 15 and 70% R enantiomer. The trapping results suggest the existence of pheromone races or sibling species among the specimens identified as E. semipurpurella.

  DOI：

  10.1007/bf02033647

文献信息

• APPLICATIONS OF THE TANDEM [2,3]-WITTIG-OXY-COPE REARRANGEMENT TO SYNTHESES OF<i>exo</i>-BREVICOMIN AND OXOCRINOL. THE SCOPE AND LIMITATION OF THE SIGMATROPIC SEQUENCES AS A SYNTHETIC METHOD FOR δ,ε-UNSATURATED KETONES
  作者：Koichi Mikami、Takeshi Nakai

  DOI：10.1246/cl.1982.1349

  日期：1982.9.5

  The synthetic utility of the title sigmatropic sequence is illustrated in the syntheses of E-6-nonen-2-one, a precursor of exo-brevicomin, and oxocrinol. The scope and limitation of this sequence as a synthetic method for δ,e-unsaturated ketones are also discussed.

  标题 sigmatropic 序列的合成效用在 E-6-nonen-2-one、exo-brevicomin 的前体和 oxocrinol 的合成中得到了说明。还讨论了该序列作为 δ,e-不饱和酮的合成方法的范围和限制。
• Synthesis of β-silyl ketones via reaction of trimethylsilyllthium with unsaturated hydrazones. Application to the synthesis of brevicomin
  作者：Paul F. Hudrlik、Anne M. Hudrlik、Tilahun Yimenu、Morris A. Waugh、G. Nagendrappa

  DOI：10.1016/s0040-4020(01)86637-0

  日期：1988.1

  undergoes conjugate addition to dimethylhydrazones of α,β-unsaturated ketones. The resulting metalloenamine intermediates can be alkylated, and the resulting hydrazone products cleaved to give α-substituted-β-silyl ketones. These reactions, together with a silicon-directed Baeyer-Villiger reaction, have been applied to the synthesis of brevicomin.

  三甲基甲硅烷基锂与α，β-不饱和酮的二甲基hydr共轭加成。可以将所得的金属烯胺中间体烷基化，并将所得的products产物裂解，得到α-取代的-β-甲硅烷基酮。这些反应，以及硅定向的Baeyer-Villiger反应，已被用于合成brevicomin。
• Stereochemistry of an oxidative 1,4-fragmentation of γ-stannyl alcohols with a hypervalent organoiodine compound and the synthesis of erythro-6-acetoxyhexadecan-5-olide
  作者：Masahito Ochiai、Tatsuzo Ukita、Yoshimitsu Nagao、Eiichi Fujita

  DOI：10.1039/c39850000637

  日期：——

  Iodine(III)-mediated oxidative 1,4-fragmentation of the 2,3-trans- and 2,3-cis-3-stannyl alcohols, (6a,b) and (6c), proceeds stereospecifically to give the E- and Z-enals, (7) and (8), respectively, and stetreoselective synthesis of the mosquito pheromone, erythro-6-acetoxyhexadecan-5-olide (5), starting from the E-enal(7), was accomplished.

  碘（III）介导的2,3-反式和2,3-顺式-3-锡烷基醇（6a，b）和（6c）的氧化1,4-片段立体定向产生E-和Z-烯醛（7）和（8）分别完成，并且从E-烯醛（7）开始，立体选择性地合成了蚊子信息素，赤型-6-乙酰氧基六癸-5-醇化物（5）。
• Lewis Acid-Induced Reactions of γ-Trialkylstannyl Ketones. Cyclization, Carbon-Carbon Bond Cleavage, and 1,5-Hydride Shift
  作者：Tadashi Sato、Kazutaka Tachibana、Akira Kawase、Tomokazu Hirose

  DOI：10.1246/cl.1993.937

  日期：1993.6

  γ-Trialkylstannyl ketones underwent cyclobutanation, C-C bond cleavage, or 1,5-hydride shift, depending upon the substitution pattern of the substrates.

  根据底物的取代模式，γ-三烷基锡酮发生了环丁烷化、C-C 键裂解或 1,5-酸酐转移。
• Ep2 Receptor Agonists
  申请人：Borman Richard Anthony

  公开号：US20080045596A1

  公开（公告）日：2008-02-21

  A compound selected from one of the following: or a salt, solvate, chemically protected form or prodrug thereof, and its use in treating conditions alleviated by agonism of an EP 2 receptor.

  从以下化合物中选择一个：或其盐、溶剂化物、化学保护形式或前药，以及其在治疗通过EP2受体激动缓解的疾病中的应用。