8-壬烯-2-酮 | 5009-32-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 8-壬烯-2-酮
• 中文别名: 正-8-壬烯-2-酮；壬-8-烯-2-酮
• 英文名称: 8-nonen-2-one
• 英文别名: non-8-en-2-one
• CAS: 5009-32-5
• 化学式: C₉H₁₆O
• mdl: MFCD11553466
• 分子量: 140.225
• InChiKey: OIFXLYCBBBXCIB-UHFFFAOYSA-N

物化性质

• LogP：
  2.52
• 物理描述：
  Colourless liquid; Fruity aroma
• 溶解度：
  Practically insoluble to insoluble in water
• 密度：
  0.853-0.855
• 折光率：
  1.436-1.437
• 保留指数：
  1055
• 稳定性/保质期：
  存在于主流烟气中。

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  10
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2914190090

制备方法与用途

生产方法：

1. 通过让1,8-二壬烯与叔丁基过氧化氢发生反应而获得。

反应信息

• 作为反应物：
  描述：

  8-壬烯-2-酮 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以81%的产率得到壬-8-烯-2-醇
  参考文献：
  名称：

  大病毒素A的组成型C 22-羧酸的不对称合成

  摘要：

  已经开发出大病毒素A的C 22-三羟基脂肪酸组分的有效不对称合成。关键步骤是高度对映选择性（i）脂肪酶催化的酰化作用；（ii）InCl 3-（S）-BINOL介导的烯丙基化作用；以及（iii）不对称二羟基化（ADH）反应。通过将所得的二醇非对映异构体转化为所需的环氧对映体，可以克服ADH反应的中等非对映选择性。

  DOI：

  10.1016/j.tet.2015.01.010
• 作为产物：
  描述：

  5-己烯醛 在 9,10-二氰基蒽 、 三苯基膦 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 80.0h， 生成 8-壬烯-2-酮
  参考文献：
  名称：

  Designing Photosystems for Harvesting Photons into Electrons by Sequential Electron-Transfer Processes:  Reversing the Reactivity Profiles of α,β-Unsaturated Ketones as Carbon Radical Precursor by One Electron Reductive β-Activation

  摘要：

  Two photosystems are developed to harvest visible-light photons into electrons via sequential electron transfer processes. Photosystem-A (PS-A) consisted of DCA as light harvesting electron acceptor and Ph3P as sacrificial electron donor, whereas photosystem-B (PS-B) employed DCA as usual electron acceptor, DMN as a primary electron donor, and ascorbic acid as a secondary and sacrificial election donor. alpha,beta-Unsaturated ketones are utilized as secondary electron acceptors. The design of these photosystems is based on the thermodynamic feasibility of electron transfer between each participating components. Electron transfer from DCA(.-) to alpha,beta-unsaturated ketones leads to their beta-activation as carbon centered radicals which cyclizes efficiently to tethered activated olefins. Cyclization with a nonactivated olefin is found to be moderate. The cyclization stereochemistries have been illustrated by studying the PET activation of 5 and 21. The exclusive trans-stereochemistry observed in 8 is explained by considering the thermodynamic, equilibration of initially formed syn-intermediate 10 from 5. The isolation of trace amount of 9 in this reaction substantiates the syn-intermediacy as primary intermediate which is further confirmed by the isolation of 25 from 21. Formation of 25 suggests that wherever the syn-intermediate is thermodynamically more stable, it invariably undergoes further cyclization to geometrically well-placed enolate double bond. An interesting observation is made by isolating 9 as a major product from the PET activation of 5 using PS-B. Stabilization of 10 by ascorbic acid is suggested to be the plausible explanation for this unusual observation. Radicals produced by the reductive beta-activation of alpha,beta-unsaturated ketones follow well established radical cyclization rules which is exemplified by studying the reactions of 39 and 40. Generality of these cyclizations is demonstrated from the PET reactions of 29-32. Synthesis of 49, an important structural framework of biologically active angularly fused triquinanes, from 48 is included in this study to demonstrate the varied applicability of this strategy.

  DOI：

  10.1021/ja9641564

文献信息

• Highly Productive α-Alkylation of Ketones with Alcohols Mediated by an Ir–Oxalamidato/Solid Base Catalyst System
  作者：Hideo Shimizu、Hironori Maeda、Hideki Nara

  DOI：10.1021/acs.oprd.0c00362

  日期：2020.11.20

  An Ir–oxalamidato complex in combination with a solid base (e.g., magnesium aluminometasilicate/Ca(OH)2) significantly improved the catalyst productivity in α-alkylation of methyl ketones with primary alcohols. Optimization through systematic variation of the oxalamidato ligand led to a practical turnover number (TON) of 10 000–40 000.

  Ir-草胺酰胺配合物与固体碱（例如，铝硅酸镁/ Ca（OH）2）结合可显着提高甲基酮与伯醇的α-烷基化反应的催化剂生产率。通过系统改变草酰胺的配体而进行的优化导致实际营业额（TON）为10,000至40,000。
• Dendrimer–Palladium Complex Catalyzed Oxidation of Terminal Alkenes to Methyl Ketones
  作者：Pumza P. Zweni、Howard Alper

  DOI：10.1002/adsc.200404013

  日期：2004.6

  complexation to dibenzylidenepalladium(0) gave the desired silica-supported dendrimer–palladium catalyst complexes G0 to G4-C2-Pd. These catalysts showed activity towards the oxidation of terminal alkenes to methyl ketones. A dependence of catalytic activity on the spacer length of the diamine in PAMAM was observed.

  制备了具有不同间隔长度的二氧化硅支撑的聚酰胺型（PAMAM）树状聚合物。引入二苯基膦基后，与二亚苄基钯（0）的络合得到所需的二氧化硅负载的树状聚合物-钯催化剂配合物G0至G4-C2-Pd。这些催化剂显示出对末端烯烃氧化为甲基酮的活性。观察到催化活性对PAMAM中二胺间隔物长度的依赖性。
• Highly efficient amphiphilic cleavage of γ-iodo carbonyl substrates with aluminum system
  作者：Yuichiro Kondo、Kana Kon-i、Takashi Ooi、Keiji Maruoka

  DOI：10.1016/s0040-4039(99)01718-9

  日期：1999.12

  CC bonds of γ-iodo carbonyl substrates has been realized by the effective use of a combined Lewis acid/base system consisting of aluminum tris(2,6-diphenylphenoxide) . This new amphiphilic bond cleavage reaction can be applied to a wide variety of γ-iodo carbonyl substrates and therefore serves as a highly efficient and general route to both cyclic and acyclic unsaturated carbonyl compounds.

  通过有效地使用由三（2,6-二苯基苯氧基铝）组成的路易斯酸/碱组合体系，已经实现了γ-碘羰基底物的αβCC键的概念上新的两亲裂解。这种新的两亲键裂解反应可应用于多种γ-碘羰基底物，因此可作为高效且通用的合成环状和非环状不饱和羰基化合物的途径。
• METHOD FOR CONVERTING HYDROXYL GROUP OF ALCOHOL
  申请人：Takasago International Corporation

  公开号：US20210047254A1

  公开（公告）日：2021-02-18

  The present invention relates to: a method for converting a hydroxyl group of an alcohol; and a catalyst which makes the method possible. A method for converting a hydroxyl group of an alcohol according to the present invention is characterized by producing a compound represented by CH(R 1 )(R 2 )Nu (wherein R 1 , R 2 and Nu are as defined below) by reacting an alcohol represented by CH(R 1 )(R 2 )OH (wherein each of R 1 and R 2 represents a hydrogen atom, an optionally substituted alkyl group, or the like) and a compound having an active proton, which is represented by H-Nu (wherein Nu represents a group represented by —CHX 1 -EWG 1 or —NR 3 R 4 ; X 1 represents a hydrogen atom or the like; EWG 1 represents an electron-withdrawing group; and each of R 3 and R 4 represents a hydrogen atom, an optionally substituted alkyl group, or the like), with each other in the presence of a complex of a group 7-11 metal of the periodic table and at least one solid base that is selected from the group consisting of layered double hydroxides, composite oxides and calcium hydroxide.

  本发明涉及：将醇的羟基转化为的方法；以及使该方法成为可能的催化剂。根据本发明的将醇的羟基转化为的方法的特征在于，在周期表的7-11族金属群的复合物存在下，通过将一个由CH(R1)(R2)OH（其中R1和R2分别表示氢原子、可选择取代的烷基基团或类似物）表示的醇与一个具有活性质子的化合物（其中Nu表示由—CHX1-EWG1或—NR3R4表示的基团；X1表示氢原子或类似物；EWG1表示电子吸引基团；R3和R4分别表示氢原子、可选择取代的烷基基团或类似物）反应，从而产生一个由CH(R1)(R2)Nu（其中R1、R2和Nu如下定义）表示的化合物。同时，所述反应中至少选择一种来自层状双氢氧化物、复合氧化物和氢氧化钙的固体碱作为催化剂。
• BITTER TASTE MODIFIERS INCLUDING SUBSTITUTED 1-BENZYL-3-(1-(ISOXAZOL-4-YLMETHYL)-1H-PYRAZOL-4-YL)IMIDAZOLIDINE-2,4-DIONES AND COMPOSITIONS THEREOF
  申请人：SENOMYX, INC.

  公开号：US20160376263A1

  公开（公告）日：2016-12-29

  The present invention includes compounds and compositions known to modify the perception of bitter taste, and combinations of said compositions and compounds with additional compositions, compounds, and products. Exemplary compositions comprise one or more of the following: cooling agents; inactive drug ingredients; active pharmaceutical ingredients; food additives or foodstuffs; flavorants, or flavor enhancers; food or beverage products; bitter compounds; sweeteners; bitterants; sour flavorants; salty flavorants; umami flavorants; plant or animal products; compounds known to be used in pet care products; compounds known to be used in personal care products; compounds known to be used in home products; pharmaceutical preparations; topical preparations; cannabis-derived or cannabis-related products; compounds known to be used in oral care products; beverages; scents, perfumes, or odorants; compounds known to be used in consumer products; silicone compounds; abrasives; surfactants; warming agents; smoking articles; fats, oils, or emulsions; and/or probiotic bacteria or supplements.

  本发明涵盖已知用于改变苦味感知的化合物和组合物，以及所述组合物和化合物与额外的组合物、化合物和产品的组合。示例组合物包括以下一种或多种：冷却剂；无活性药物成分；活性药用成分；食品添加剂或食品；调味剂或调味增强剂；食品或饮料产品；苦味化合物；甜味剂；苦味剂；酸味调味剂；咸味调味剂；鲜味调味剂；植物或动物产品；已知用于宠物护理产品中的化合物；已知用于个人护理产品中的化合物；已知用于家用产品中的化合物；制药制剂；局部制剂；大麻衍生或与大麻相关的产品；已知用于口腔护理产品中的化合物；饮料；香味、香水或除臭剂；已知用于消费品中的化合物；硅化合物；磨料；表面活性剂；发热剂；吸烟物品；脂肪、油脂或乳化剂；和/或益生菌或补充剂。

表征谱图