香茅醛肟 | 135500-74-2

• 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
• 中文名称: 香茅醛肟
• 英文名称: rac-E-3,7-dimethyloct-6-enaldehyde oxime
• 英文别名: Citronellaldoxime；citronellal oxime；3,7-dimethyl-oct-6-enal oxime；3,7-Dimethyl-Oct-6-en-1-al-Oxim；(NE)-N-(3,7-dimethyloct-6-enylidene)hydroxylamine
• CAS: 135500-74-2
• 化学式: C₁₀H₁₉NO
• 分子量: 169.267
• InChiKey: JUCCIEVMICHZPK-DHZHZOJOSA-N

物化性质

• 沸点：
  130 °C(Press: 13 Torr)
• 密度：
  0.8920 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  香茅醛肟 在 chloroamine-T 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以82%的产率得到trimethyl-3,3,6 hexahydro-3,3a,4,5,6,7 benzioxazole-2,1
  参考文献：
  名称：

  A New Method for the Generation of Nitrile Oxides and Its Application to the Synthesis of 2-Isoxazolines

  摘要：

  醛肟与氯胺-T 反应会生成腈氧化物，腈氧化物可在分子内或分子间与烯烃化合物发生原位反应，从而以良好的收率生成异噁唑啉。

  DOI：

  10.1055/s-1989-27152
• 作为产物：
  描述：

  香茅醛 在 盐酸羟胺 、 sodium carbonate 作用下， 以 乙醇 、 水 为溶剂， 生成 香茅醛肟
  参考文献：
  名称：

  Arthropod maturation inhibitors

  摘要：

  一些萜类化合物及其环氧化物被合成，并发现当应用于生长阶段较早的昆虫时，可以防止昆虫的成熟。

  公开号：

  US03933865A1

文献信息

• Cyanide-Free and Broadly Applicable Enantioselective Synthetic Platform for Chiral Nitriles through a Biocatalytic Approach
  作者：Tobias Betke、Philipp Rommelmann、Keiko Oike、Yasuhisa Asano、Harald Gröger

  DOI：10.1002/anie.201702952

  日期：2017.9.25

  A cyanide‐free platform technology for the synthesis of chiral nitriles by biocatalytic enantioselective dehydration of a wide range of aldoximes is reported. The nitriles were obtained with high enantiomeric excess of >90 % ee (and up to 99 % ee) in many cases, and a “privileged substrate structure” with respect to high enantioselectivity was identified. Furthermore, a surprising phenomenon was observed

  报道了通过多种醛糖肟的生物催化对映选择性脱水合成手性腈的无氰化平台技术。具有高对映体过量> 90％的得到的腈EE（和高达99％ee值）在许多情况下，和“特权基板结构”相对于高对映选择性鉴定。此外，观察到令人惊讶的对映体特异性现象，通常在酶催化中没有观察到。取决于是否使用 外消旋醛肟肟底物的E或Z异构体，优选用相同的酶形成相应腈的一种或另一种对映体。
• Beckmann Rearrangement of Oximes under Very Mild Conditions
  作者：Lidia De Luca、Giampaolo Giacomelli、Andrea Porcheddu

  DOI：10.1021/jo025960d

  日期：2002.8.1

  A variety of ketoximes, easily prepared from the corresponding ketones, undergo the Beckmann rearrangement upon treatment with 2,4,6-trichloro[1,3,5]triazine in N,N-dimethylformamide at room temperature in excellent yields. This procedure can be applied to aldoximes for obtaining the corresponding nitriles.

  容易从相应的酮制得的各种酮肟在室温下用N，N-二甲基甲酰胺中的2,4,6-三氯[1,3,5]三嗪处理后，以优异的收率进行贝克曼重排。该程序可以应用于醛肟以获得相应的腈。
• Aromachemicals
  申请人：Turin Luca

  公开号：US20060094640A1

  公开（公告）日：2006-05-04

  Improved aromachemical derivatives, and fragrances and flavorings including the derivatives, that have a longer useful shelf life than the aromachemicals from which they can be derived, are disclosed. In particular, the derivatives maintain the fragrance characteristics of the aromachemicals, while lowering the allergic properties, increasing the stability, and/or increasing the odor intensity. Also disclosed are methods of making the derivatives, and articles of manufacture including the derivatives. In one embodiment, the derivatives are prepared by replacing one or more double bonds in citral with a thioether, cyclopropyl, oxirane, or thiirane group. The cyclopropane ring can be unsubstituted, or substituted with one or two lower alkyl, preferably methyl groups. The alkyl groups can optionally be substituted, for example, with electron donating groups, electron with drawing groups, groups which increase the hydrophilicity or hydrophobocity, and the like. In another embodiment, the derivatives are prepared by replacing the aldehyde group in the essential oil with a nitrile, methyl ether or acetal group. The acetal groups can provide the compounds with a long lasting flavor or fragrance, where the acetals slowly hydrolyze to provide the aldehyde group in the parent essential oil. In some embodiments, both the aldehyde and at least one of the double bond functional groups are both derivatized as described herein. Examples of suitable articles of manufacture include candles, air fresheners, perfumes, disinfectant compositions, hypochlorite (bleach) compositions, beverages such as beer and soda, denture cleanser tablets and flavored orally-delivered products such as lozenges, candies, and the like.

  本发明公开了改良的芳香化学衍生物，以及包含这些衍生物的香料和调味料，它们的有效货架寿命比它们可以衍生的芳香化学品更长。特别是，这些衍生物保持了芳香化学品的香气特性，同时降低了过敏性，增加了稳定性和/或增加了气味强度。本发明还公开了制备这些衍生物的方法以及包括这些衍生物的制品。在一个实施例中，这些衍生物是通过用硫醚、环丙基、环氧烷或硫代环氧烷基取代柠檬醛中的一个或多个双键来制备的。环丙烷环可以是未取代的，或者用一个或两个较低的烷基，优选是甲基基取代。烷基可以选择性地被取代，例如，用电子给予基团，电子吸引基团，增加亲水性或疏水性的基团等。在另一个实施例中，这些衍生物是通过用腈、甲醚或缩醛基取代精油中的醛基来制备的。缩醛基可以为化合物提供持久的风味或香气，其中缩醛缓慢水解以提供母体精油中的醛基。在一些实施例中，醛基和至少一个双键官能团都是根据本文所述进行衍生的。适当的制品包括蜡烛、空气清新剂、香水、消毒剂组合物、次氯酸盐（漂白剂）组合物、啤酒和苏打水等饮料、假牙清洁剂片和口味制品，例如含片、糖果等。
• A process for producing nitrile compounds
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：EP0080700A1

  公开（公告）日：1983-06-08

  In a process for producing a nitrile compound from a corresponding aldehyde exhibited by the general formula (I) and a hydroxylamine inorganic acid salt or from an aldoxime exhibited by the general formula (II), (In the general formulas shown hereinabove, R' represents an aryl group having 6 to 9 carbon atoms and R2 represents an alkyl or alkenyl group having 1 to 9 carbon atoms or an aryl group having 6 to 9 carbon atoms), a process, wherein water produced in the reaction is azeotropically distilled out of the reaction system with the aid of a solvent which makes an azeotropic mixture with water. The nitrile compound is useful as an important intermediate for the synthesis of pharmaceuticals or pesticides.

  在由通式(I)所示的相应醛和羟胺无机酸盐或由通式(II)所示的醛肟生产腈化合物的工艺中，（在上述通式中，R'代表具有 6 至 9 个碳原子的芳基，R2 代表具有 1 至 9 个碳原子的烷基或烯基或具有 6 至 9 个碳原子的芳基），反应中产生的水借助与水共沸的溶剂从反应体系中蒸馏出来。 腈化合物可作为合成药物或农药的重要中间体。
• Improved aromachemicals
  申请人：Flexitral, Inc.

  公开号：EP1705171A1

  公开（公告）日：2006-09-27

  The present invention provides a derivative of an aromachemical obtainable by a process which comprises replacing at least one double bond in an aromachemical by a three-membered ring, wherein the three membered ring includes the two carbons of the double bond, each of which is bonded to an oxygen, a sulfur or a C(R)2 group, wherein R is, independently, H, C1-5 alkyl or C1-5 substituted alkyl, and wherein the substituents on the substituted alkyl groups are selected from the group consisting of halo, hydroxy, thiol, thioether, amine, carboxylic acid, ester, nitro, cyano, sulfonic acid, urea, and thiourea.

  本发明提供了一种芳香族化合物的衍生物，可通过一种工艺获得，该工艺包括用三元环取代芳香族化合物中的至少一个双键，其中三元环包括双键的两个碳，每个碳都与氧键合、硫或 C(R)2 基团，其中 R 独立地为 H、C1-5 烷基或 C1-5 取代的烷基，而取代的烷基上的取代基选自卤、羟基、硫醇、硫醚、胺、羧酸、酯、硝基、氰基、磺酸、脲和硫脲组成的组。