5-Methylheptanal | 75579-88-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-Methylheptanal
• 英文别名: 5-methyl-heptanal；anteisocaprylaldehyde
• CAS: 75579-88-3
• 化学式: C₈H₁₆O
• 分子量: 128.214
• InChiKey: RRTVBKXBOQHBMV-UHFFFAOYSA-N

物化性质

• 沸点：
  72 °C(Press: 25 Torr)
• 密度：
  0.8164 g/cm3(Temp: 25 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  9
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  5-Methylheptanal 在 重铬酸吡啶 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 7-Methylnonan-3-one
  参考文献：
  名称：

  Hesperophylax occidentalis (Trichoptera: Limnephilidae): Electroantennogram structure-activity study of sex pheromone component 6-methylnonan-3-one

  摘要：

  Electroantennogram (EAG) analyses of Hesperophylax occidentalis male and female antennae were used to generate dose-response curves for synthetic, racemic 6-methylnonan-3-one and to demonstrate the chemical specificity of male antennal olfactory cells. Male antennae responded to 6-methylnonan-3-one, the main female pheromone component. Females also demonstrated a response to 6-methylnonan-3-one, but a smaller one than males. The chemical specificity of male antennal receptors was determined by comparing EAG activity of synthetic, racemic 6-methylnonan-3-one and a series of structural analogs. The three structural parameters considered, including keto position, chain length, and methyl-group position, were demonstrated to contribute significantly to the reception of synthetic, racemic 6-methylnonan-3-one by male antennae. For straight-chain nonanones with keto groups at different positions, nonan-3-one elicited the greatest EAG responses from male antennae. For straight-chain alkan-3-ones with different chain lengths, the EAG responses of male antennae to nonan-3-one and decan-3-one were the same, but greater than those to other chain lengths. For methyl-branched nonan-3-ones, 6-methylnonan-3-one elicited greater EAG responses from antennae than analogs with the methyl group at another position.

  DOI：

  10.1007/bf02040204
• 作为产物：
  描述：

  5-甲基-1-庚醇 在 hydrous zirconium(IV) oxide modified with Me₃SiCl 、 3-甲基苯甲醛 作用下， 以 xylene 为溶剂， 以69%的产率得到5-Methylheptanal
  参考文献：
  名称：

  醇在三甲基氯化硅烷改性的水合氧化锆（IV）上氧化成醛和酮

  摘要：

  通过三甲基氯硅烷与水合氧化锆(IV)反应制备改性催化剂。然后通过使用羰基化合物作为氢受体将其应用于醇的氧化。在环烷醇的情况下，氧化有效地进行以产生相应的酮。此外，伯脂肪醇在间歇反应系统中以高产率转化为相应的醛。此外，还研究了氧化受各种溶剂和氢受体的影响。

  DOI：

  10.1246/bcsj.66.1699

文献信息

• Processes for preparing beta-hydroxy-ketones and alpha,beta-unsaturated ketones
  申请人：Barnicki Donald Scott

  公开号：US20050004401A1

  公开（公告）日：2005-01-06

  Processes for producing β-hydroxy-ketones and α,β-unsaturated ketones are disclosed which comprise the crossed condensation of an aldehyde with a ketone in the presence of a hydroxide or alkoxide of alkali metal or an alkaline earth metal as catalyst. The products of the process, β-hydroxy-ketones and α,β-unsaturated ketones, are useful for the preparation of many commercially important products in the chemical process industries including solvents, drug intermediates, flavors and fragrances, other specialty chemical intermediates.

  披露了生产β-羟基酮和α,β-不饱和酮的过程，这些过程包括在碱金属或碱土金属的氢氧化物或醇盐的催化下，醛与酮的交叉缩合。该过程的产品，即β-羟基酮和α,β-不饱和酮，对于化学工艺工业中许多商业上重要产品的制备非常有用，包括溶剂、药物中间体、香精和香料、以及其他专用化学品中间体。
• CARBOXYLIC ACID DERIVATIVES AND ADHESION MOLECULE INHIBITORS CONTAINING THE SAME AS THE ACTIVE INGREDIENT
  申请人：TORAY INDUSTRIES, INC.

  公开号：EP1209147A1

  公开（公告）日：2002-05-29

  Prevention or therapy of inflammatory diseases caused by invasion of leukocytes such as monocytes, lymphocytes and eosinophils, by providing a substance which inhibits cell adhesion via an adhesion molecule, especially adhesion molecule VLA-4, is disclosed. A group of carboxylic acid derivatives represented by, for example, and adhesion molecule inhibitors comprising the same as an effective ingredient were provided.

  通过提供一种通过粘附分子抑制细胞粘附的物质，特别是粘附分子VLA-4，来预防或治疗由单核细胞、淋巴细胞和嗜酸性粒细胞侵袭引起的炎症性疾病的方法被揭示。提供了一组由羧酸衍生物代表的粘附分子抑制剂，例如，以其为有效成分的粘附分子抑制剂。
• PROCESS FOR THE PRODUCTION OF NEOPENTYLGLYCOL USING FORMALDEHYDE WITH A LOW METHANOL CONTENT
  申请人：Sirch Tilman

  公开号：US20080004475A1

  公开（公告）日：2008-01-03

  A process is provided for the preparation of polymethylol compounds of formula (I): (HOCH 2 ) 2 —C—(R) 2 ,   (I) in which the radicals R independently of one another are each a further methylol group, an alkyl group having from 1 to 22 C atoms or an aryl or aralkyl group having from 6 to 22 C atoms, by (a) condensing aldehydes having from 2 to 24 C atoms with formaldehyde in an aldol reaction using tertiary amines as a catalyst to give alkanals of formula (II): in which the radicals R independently of one another are each as defined above, (b) then separating, by distillation, the reaction mixture obtained into a bottom product comprising predominantly the compounds of formula II and a low-boiling stream consisting of unconverted or partially converted starting materials, and (c) hydrogenating the distillation bottom, wherein the aldol reaction is carried out with an aqueous formaldehyde solution having a methanol content of 0.35 to 0.5% by weight of methanol, the low-boiling stream is separated off at a pressure of 1 to 3 bar and temperatures of 100 to 135° C. and completely or partially recycled into the aldol reaction. This procedure advantageously makes it possible specifically to prevent the formation of by-products and hence to increase the yield of the desired polymethylol compound. We have found that this object is achieved by a process for the preparation of polymethylol compounds of formula (I): (HOCH 2 ) 2 —C—(R) 2 ,   (I) in which the radicals R independently of one another are each a further methylol group, an alkyl group having from 1 to 22 C atoms or an aryl or aralkyl group having from 6 to 22 C atoms, by (a) condensing aldehydes having from 2 to 24 C atoms with formaldehyde in an aldol reaction using tertiary amines as a catalyst to give alkanals of formula (II): in which the radicals R independently of one another are each as defined above, (b) then separating, by distillation, the reaction mixture obtained (aldolization product) into a bottom product comprising predominantly the compounds of formula II and a low-boiling stream consisting of unconverted or partially converted starting materials, and (c) hydrogenating the distillation bottom, wherein the aldol reaction is carried out with an aqueous formaldehyde solution having a methanol content of 0.35 to 0.5% by weight, the separation of the low-boiling stream is effected at a pressure of 1.1 to 3 bar, preferably 1.5 bar, and a temperature of 100 to 135° C., preferably of 102 to 125° C., and the low-boiling stream is completely or partially recycled into the aldol reaction, preferably the entire low-boiling stream being recycled. In the aldol reaction, a partially converted starting compound of formula (III): can also be formed in which the radicals R independently of one another are each hydrogen or are as defined above. According to the invention, this partially converted starting compound of formula (III), together with the desired alkanal of formula (II), is separated from the other by-products and the unreacted starting compounds and reacted again in an aldol reaction with formaldehyde having a methanol content of 0.35% by weight to 0.5% by weight, using tertiary amines as a catalyst.

  提供了一种制备通式(I)的聚羟甲基化合物的方法：(HOCH2)2—C—(R)2，其中R基团彼此独立地分别为另一个羟甲基、具有1至22个碳原子的烷基、或具有6至22个碳原子的芳基或芳烷基，该方法包括：(a) 在叔胺催化剂存在下，通过醇醛反应将具有2至24个碳原子的醛与甲醛缩合，得到通式(II)的烷基醛：其中R基团彼此独立地如上定义，(b) 然后通过蒸馏将获得的反应混合物分离成主要包含通式(II)化合物的底部产物和由未转化或部分转化的起始材料组成的低沸点流，以及(c) 氢化蒸馏底部，其中醇醛反应使用含有0.35%至0.5%重量甲醇的甲醛水溶液进行，低沸点流在1至3巴的压力和100至135°C的温度下分离，并完全或部分循环回醇醛反应中。这种方法特别有利于防止副产物的形成，从而提高所需聚羟甲基化合物的收率。我们发现，通过一种制备通式(I)的聚羟甲基化合物的方法可以实现这一目标：(HOCH2)2—C—(R)2，其中R基团彼此独立地如上定义，该方法包括：(a) 在叔胺催化剂存在下，通过醇醛反应将具有2至24个碳原子的醛与甲醛缩合，得到通式(II)的烷基醛：其中R基团彼此独立地如上定义，(b) 然后通过蒸馏将获得的反应混合物（醇醛化产物）分离成主要包含通式(II)化合物的底部产物和由未转化或部分转化的起始材料组成的低沸点流，以及(c) 氢化蒸馏底部，其中醇醛反应使用含有0.35%至0.5%重量甲醇的甲醛水溶液进行，低沸点流的分离在1.1至3巴的压力下进行，优选1.5巴，温度为100至135°C，优选102至125°C，低沸点流完全或部分循环回醇醛反应中，优选整个低沸点流循环。在醇醛反应中，还可以形成部分转化的起始化合物通式(III)：其中R基团彼此独立地分别为氢或如上定义。根据本发明，这种部分转化的起始化合物通式(III)与所需的烷基醛通式(II)一起，从其他副产物和未反应的起始化合物中分离出来，并在叔胺催化剂存在下，使用含有0.35%重量至0.5%重量甲醇的甲醛进行再次醇醛反应。
• PROCESS FOR PREPARING POLYALCOHOLS FROM FORMALDEHYDE HAVING A LOW FORMIC ACID CONTENT
  申请人：Sirch Timan

  公开号：US20080167506A1

  公开（公告）日：2008-07-10

  The invention relates to a process for preparing polymethylol compounds of the formula (I) (HOCH 2 ) 2 —C—R 2 (I) where the radicals R are each, independently of one another, a further methylol group or an alkyl group having from 1 to 22 carbon atoms or an aryl or aralkyl group having from 6 to 22 carbon atoms, by condensation of aldehydes having from 2 to 24 carbon atoms with formaldehyde in an aldol reaction using tertiary amines as catalyst to form alkanals of the formula (II) where the radicals R each independently have one of the abovementioned meanings, and subsequent hydrogenation of the latter. The particular inventive feature of this process is that the aldol reaction is carried out using an aqueous formaldehyde solution having a formic acid content of <150 ppm and preferably <100 ppm. In this way of carrying out the process, the formation of by-products can advantageously be prevented in a targeted manner and the yield of the desired polymethylol compound can thereby be increased.

  该发明涉及一种制备多羟甲基化合物的方法，其化学式为(I)(HOCH2)2—C—R2(I)，其中基团R分别独立地为另一个甲醇基团或具有1至22个碳原子的烷基基团或具有6至22个碳原子的芳香基或芳基烷基基团，通过将具有2至24个碳原子的醛与甲醛在醛缩反应中使用三级胺作为催化剂进行缩合，形成化学式(II)的脂醛，其中基团R各自独立地具有上述含义之一，并随后对其进行氢化。该方法的特殊创新特点在于，在使用含有甲醛的水溶液进行醛缩反应时，其甲酸含量小于150 ppm，最好小于100 ppm。通过采用这种方法进行处理，可以有针对性地防止副产物的形成，并从而增加所需多羟甲基化合物的产率。
• METHOD FOR PREPARING POLYMETHYLOLS
  申请人：Sirch Tilman

  公开号：US20120004472A1

  公开（公告）日：2012-01-05

  The present invention relates to a process for distilling an aqueous polymethylol mixture which comprises a polymethylol of the formula (I) (HOCH 2 ) 2 —C—R 2 (I) in which each R is independently a further methylol group or an alkyl group having 1 to 22 carbon atoms or an aryl or aralkyl group having 6 to 22 carbon atoms, a tertiary amine, water and the adduct of tertiary amine and formic acid (amine formate), which comprises performing the distillation in a distillation column which is connected at the bottom to an evaporator, the bottom temperature being above the evaporation temperature of the monoester of formic acid and polymethylol (polymethylol formate) which forms during distillation. The present invention further relates to a composition comprising polymethylol and 1 to 10 000 ppm by weight of polymethylol formate, and to the use thereof.

  本发明涉及一种蒸馏含水多羟甲基混合物的工艺，该混合物包含通式(I)的多羟甲基化合物(HOCH2)2—C—R2(I)，其中每个R独立地为另一个羟甲基团或具有1至22个碳原子的烷基团，或具有6至22个碳原子的芳基或芳烷基团，以及叔胺、水和叔胺与甲酸的加合物（胺甲酸酯），该工艺包括在连接于底部蒸发器的蒸馏塔中进行蒸馏，底部温度高于蒸馏过程中形成的一甲酸酯和多羟甲基化合物（多羟甲基甲酸酯）的蒸发温度。本发明还涉及包含多羟甲基化合物及1至10000ppm重量的多羟甲基甲酸酯的组合物及其用途。