(E)-1-ethoxyhept-1-ene | 16627-11-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-1-ethoxyhept-1-ene
• 英文别名: ethyl 1-heptenyl ether；1t-ethoxy-hept-1-ene；1-Ethoxy-1-heptene
• CAS: 16627-11-5
• 化学式: C₉H₁₈O
• 分子量: 142.241
• InChiKey: SDTIAHWPSZKYHU-CMDGGOBGSA-N

物化性质

• 沸点：
  165-168 °C
• 密度：
  0.8033 g/cm3(Temp: 25 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  10
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-1-ethoxyhept-1-ene 在 三甲基氯硅烷 、 Benzyltriethylammonium borohydride 、 氧气 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以80%的产率得到正庚醇
  参考文献：
  名称：

  烯醇醚与苄基三乙基氢硼化铵和三甲基氯硅烷的新颖而不同寻常的反应

  摘要：

  已发现苄基三乙基硼氢化铵-氯三甲基硅烷试剂体系在非常温和的反应条件下，与环状和环状烯醇醚1进行新颖而不同寻常的反应，分别分别高收率地分别生成二醇和醇2。

  DOI：

  10.1016/s0040-4039(00)60976-0
• 作为产物：
  描述：

  溴丁基-镁 、 丙烯醛缩二乙醇 以 乙醚 为溶剂， 生成 (E)-1-ethoxyhept-1-ene
  参考文献：
  名称：

  Quelet,R. et al., Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques, 1967, vol. 264, p. 1316 - 1319

  摘要：

  DOI：

文献信息

• Oxidation of Diols and Ethers by NaBrO₃/NaHSO₃Reagent
  作者：Satoshi Sakaguchi、Daisuke Kikuchi、Yasutaka Ishii

  DOI：10.1246/bcsj.70.2561

  日期：1997.10

  NaBrO3 combined with NaHSO3 was found to be an excellent oxidizing reagent of alcohols, diols, and ethers under mild conditions. A variety of aliphatic and cyclic diols were selectively oxidized with satisfactory yields to the corresponding hydroxy ketones and/or diketones, which are difficult to selectively prepare due to a concomitant formation of cleaved products. For example, 2-hydroxycyclohexanone and 1,2-cyclohexanedione were selectively formed by allowing 1,2-cyclohexanediol to react with NaBrO3/NaHSO3 reagent in a selected solvent. On the other hand, an alkyl ether, such as dioctyl ether, reacted with NaBrO3/NaHSO3 in water at room temperature to give octyl octanoate in 82% yield. The same oxidation at higher temperature (60 °C) produced the α-brominated ester, octyl 2-bromooctanoate, which is considered to be formed through an alkenyl alkyl ether as the intermediate. The treatment of 1-ethoxy-1-heptene with NaBrO3/NaHSO3 afforded ethyl 2-bromoheptanoate and 2-bromoheptanoic acid as the major products.

  NaBrO3与NaHSO3组合被发现是一种在温和条件下对醇、二醇和醚类具有优异氧化能力的试剂。多种脂肪族和环状二醇被选择性地氧化为相应的羟基酮和/或二酮，产率令人满意，这些产物由于伴随生成断裂产物而难以选择性制备。例如，通过在选定溶剂中使1,2-环己二醇与NaBrO3/NaHSO3试剂反应，选择性地生成了2-羟基环己酮和1,2-环己二酮。另一方面，在室温下，二辛醚在水中的NaBrO3/NaHSO3反应以82%的产率得到了辛基辛酸酯。同样的氧化反应在较高温度（60°C）下产生了α-溴代酯，即辛基2-溴辛酸酯，这被认为是通过烯基烷基醚作为中间体形成的。使用NaBrO3/NaHSO3处理1-乙氧基-1-庚烯，主要产物是乙基2-溴庚酸酯和2-溴庚酸。
• Borata-Wittig olefination reactions of ketones, carboxylic esters and amides with bis(pentafluorophenyl)borata-alkene reagents
  作者：Tongdao Wang、Sonja Kohrt、Constantin G. Daniliuc、Gerald Kehr、Gerhard Erker

  DOI：10.1039/c7ob01591g

  日期：——

  PhCH2CH2–). They underwent “non-classical” borata-Wittig olefination reactions with ethylformate to give the respective enolether carbonylation products, or their C1-elongated aldehydes (after hydrolysis). The borata-alkene [Ph–(CH2)2–CHB(C6F5)2−] [Li+HTMP] (16a) gave the respective “non-classical” borata-Wittig olefination products, the enolethers 25a,b and 27, respectively, upon treatment with methyl- or ethyl

  用LiTMP对强亲电性硼烷衍生物氨基– CH 2 CH 2 CH 2 –B（C 6 F 5）2 6进行质子化，得到硼烷-烯烃[氨基–（CH 2）2 –CH B（C 6 ˚F 5）2 - ] [李+ ]} 2 9其中后行轻便[2 + 2]与二苯甲酮或芴酮，得到相应的1,2- oxaboretanides环加成反应11A，b 。化合物9和11通过X射线衍射表征。化合物11a，b的热解或水解得到相应的borata-Wittig烯化产物12a，b。类似地，各种R–CH 2 –CH 2 –B（C 6 F 5）2硼烷（通常是通过将末端烯烃R–CH CH 2与Piers's硼烷[HB（C 6 F 5）2 ]加氢硼化生成）去质子化，得到相应的硼烷链烯烃16a–e（R：Ph–CH 2 –，n C 4 H 9，tBu，Cy，PhCH 2 CH 2 –）。他们与甲酸乙酯进行了“非经典”的borata-Witt
• METHODS FOR LABELING A SUBSTRATE USING A HETERO-DIELS-ALDER REACTION
  申请人：POPIK VLADIMIR V.

  公开号：US20110108411A1

  公开（公告）日：2011-05-12

  Methods for labeling a substrate using a hetero-Diels-Alder reaction are disclosed. The hetero-Diels-Alder reaction includes the reaction of an o-quinone methide (e.g., an o-naphthoquinone methide) with a polarized olefin to form a hetero-Diels-Alder adduct. The o-quinone methide or the polarized olefin can be attached to a surface of a substrate, and the other of the o-quinone methide or the polarized olefin can include a detectable label. The o-quinone methide can conveniently be generated by irradiation of a precursor compound, preferably in an aqueous solution, suspension, or dispersion.

  公开了使用异构Diels-Alder反应标记基底的方法。异构Diels-Alder反应包括将邻苯二酚亚甲基（例如，邻萘醌亚甲基）与极化烯烃反应，形成异构Diels-Alder加合物。邻苯二酚亚甲基或极化烯烃可以附着在基底的表面上，另一个邻苯二酚亚甲基或极化烯烃可以包含可检测的标记。邻苯二酚亚甲基可以通过辐照前体化合物方便地生成，最好在水溶液、悬浮液或分散液中。
• Selective Oxidation of Vinyl Ethers and Silyl Enol Ethers with Hydrogen Peroxide Catalyzed by Peroxotungstophosphate
  作者：Hiroyo Yamamoto、Masaya Tsuda、Satoshi Sakaguchi、Yasutaka Ishii

  DOI：10.1021/jo970440h

  日期：1997.10.1

  equivalent of 2-hydroxyoctanal, in 70% yield. The oxidation of acyclic silyl enol ethers such as 1-[(trimethylsilyl)oxy]-1-octene under these conditions gave 1-hydroxy-2-octanone in 72% yield, while the same oxidation in dichloromethane alone resulted in cleavage of the enol double bond to form heptanal in 71% yield. Cyclic silyl enol ethers were converted into the corresponding alpha-hydroxy ketones in 48-71%

  首先通过使用过氧钨磷磷酸盐（PCWP）作为催化剂，用过氧化氢水溶液氧化乙烯基和甲硅烷基烯醇醚。例如，在室温下，在甲醇和二氯甲烷的混合溶剂中，在存在PCWP（0.5 mol％）的情况下，化学计量为35％H（2）O（2）的1-乙氧基-1-辛烯的氧化反应1-乙氧基-1-甲氧基-2-羟基辛烷（2-羟基辛醛的合成当量），产率为70％。在这些条件下，无环甲硅烷基烯醇醚如1-[（（三甲基甲硅烷基）氧基] -1-辛烯的氧化以72％的收率得到1-羟基-2-辛酮，而仅在二氯甲烷中的相同氧化导致烯醇的裂解。双键形成庚醛，产率为71％。
• Acyclic enol ethers, isomers thereof, organoleptic uses thereof and processes for preparing same
  申请人：——

  公开号：US20040013779A1

  公开（公告）日：2004-01-22

  Described are synthetically produced substantially pure enol ether compositions which are cis and/or trans isomers of enol ethers having the structures: 1 wherein R 1 is C 4 -C 10 straight chain alkyl or C 9 8-alkenyl; and wherein R 2 is C 1 -C 4 alkyl, C 3 -C 4 2-alkenyl, C 4 3-alkenyl or C 10 non-allenic alkadienyl and uses thereof in imparting, augmenting or enhancing the aroma and/or taste of a consumable material such as a perfume composition, a cologne, a perfumed article such as a soap, cosmetic, hair preparation or detergent, a foodstuff, a chewing gum or an alcoholic or non-alcoholic beverage such as a carbonated beverage or fruit liquer. Also described is a process for synthesis of such enol ethers by means of (i) first forming an acetal having the structure: R 1 —CH 2 —CH(OR 2 ) 2 (ii) then carrying out a thermal decomposition reaction at pH<7 and then (iii) fractionally distilling the resulting reaction product to provide the enol ether.

  本文介绍了合成的基本纯度的烯醇醚组合物，其为具有以下结构的烯醚的顺式和/或反式异构体：其中，R1为C4-C10直链烷基或C9-C8烯基；R2为C1-C4烷基，C3-C4 2-烯基，C4-3烯基或C10非亚麻烯烷基，以及其在赋予、增强或提高可食用物质的香味和/或口感方面的用途，如香水组合物、古龙香水、香皂、化妆品、发制品或洗涤剂、食品、口香糖或酒精或非酒精饮料，如碳酸饮料或果汁酒。本文还介绍了通过以下方法合成这种烯醇醚的过程：(i)首先形成具有结构的缩醛：R1—CH2—CH(OR2)2(ii)然后在pH<7的条件下进行热分解反应，然后(iii)分馏所得的反应产物以提供烯醚。