(3R)-3,7-dimethyl-6-oxo-octanal

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R)-3,7-dimethyl-6-oxo-octanal
• 英文别名: (R)-3,7-dimethyl-6-oxooctanal；(3r)-3,7-Dimethyl-6-oxooctanal
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: QMGXVXFKXOTDMW-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3R)-3,7-dimethyl-6-oxo-octanal 在 吡啶 、 三乙酰氧基硼氢化钠 、 间氯过氧苯甲酸 、 sodium iodide 作用下， 以 二氯甲烷 、 氯仿 、 丙酮 为溶剂， 反应 21.5h， 生成 isopropyl (R)-4-methyl-6-iodohexanoate
  参考文献：
  名称：

  Synthesis of the Promising Chiral Synthon Isopropyl-4R-Methyl-6-Iodohexanoate from L-(-)-Menthol

  摘要：

  基于 L-(-)-薄荷醇（(R)-p-menth-3-ene）发生区域特异性脱水反应的产物臭氧分解转化为 2,6R-二甲基-8-羟基辛烷-3-酮的过程，提出了一种很有前景的光学纯合成物异丙基-4R-甲基-6-碘己酸酯的合成方法。

  DOI：

  10.1007/s10600-005-0070-6
• 作为产物：
  描述：

  (1R)-menth-3-ene 生成 (3R)-3,7-dimethyl-6-oxo-octanal
  参考文献：
  名称：

  [EN] NOVEL CYCLIC OXYGENATED COMPOUNDS HAVING COOLING, FRAGRANCE, AND FLAVOR PROPERTIES, AND USES THEREOF
  [FR] NOUVEAUX COMPOSES CYCLIQUES OXYGENES POSSEDANT DES PROPRIETES DE RAFRAICHISSEMENT, DE FRAGRANCE ET DE SAVEUR, ET UTILISATIONS DESDITS COMPOSES

  摘要：

  公开号：

  WO2005049562A3

文献信息

• Synthesis from L-menthol of optically active macrolides with N-containing (azine or hydrazide) groups
  作者：G. Yu. Ishmuratov、G. R. Mingaleeva、M. P. Yakovleva、R. R. Muslukhov、E. M. Vyrypaev、E. G. Galkin、A. G. Tolstikov

  DOI：10.1007/s10600-009-9407-x

  日期：2009.7

  Potentially useful 15- and 20-membered macrolides containing azine or hydrazide groups were synthesized from L-menthol via [1+1]-condensation at room temperature of 3R,7-dimethyl-6-oxooctyl-3R,7-dimethyl-6-oxooctanoate, which was obtained from 3R,7-dimethyl-6-oxooctanal via a Tishchenko reaction, with hydrazine hydrate or malonic acid dihydrazide.

  含有吖嗪或酰肼基团的潜在有用的15元和20元大环内酯是由L-薄荷醇通过3R,7-二甲基-6-氧代辛基-3R,7-二甲基-6-在室温下的[1+1]-缩合合成的。辛酸氧酯，由3R,7-二甲基-6-氧代辛醛与水合肼或丙二酸二酰肼通过Tishchenko反应得到。
• Novel Cyclic Oxygenated Compounds Having Cooling, Fragrance, and Flavor Properties, and Uses Thereof
  申请人：Selifonov Sergey

  公开号：US20070274928A1

  公开（公告）日：2007-11-29

  Compositions that include compounds capable of producing a cooling sensory effect such as certain hydroxy-ketones and hydroxy-aldehyde compounds, their cyclic semi-ketals and semiacetals, and other derivatives thereof. The compounds impart a refreshing and cooling sensation of long duration and high potency, and thus are useful in a variety of formulations, including consumer products such as mouth formulations, food and beverage products, tobacco and smoking articles, fragrances, toiletries, ointments, and the like.

  这段话的意思是：包括某些羟基酮和羟基醛化合物、它们的环状半酮和半缩醛以及其他衍生物在内的化合物，可以产生冷却感官效应的组合物。这些化合物具有长时间和高效的清爽和冷却感觉，因此在各种配方中非常有用，包括消费品如口腔制剂、食品和饮料制品、烟草和吸烟用品、香水、化妆品、药膏等。
• Phosphonium Ion-Tethered Secondary Amines for Chemospecific 5-<i>Enolexo</i> Aldol Condensations of 6-Ketoaldehydes
  作者：Akash Sugunan、V. M. Aparna、Goreti Rajendar

  DOI：10.1021/acs.joc.3c02285

  日期：2023.12.15

  targets five-membered carbo- and heterocyclic aldehydes, involving unusual aldehydes as donors and ketones as acceptors. Especially, enolizable aryl keto aldehydes and heteroatom-embedded ketoaldehydes exclusively produced cyclized products with our new catalyst, while other catalysts provided predominantly self-aldol or decomposed products. The scope and diversity of the method demonstrated by synthesizing

  使用基于脯氨酸的烷基鏻离子催化剂，提出了一种新型且高选择性的 6-酮醛的 5- enolexo - exo - trig醛醇缩合反应。大体积且亲氧的鏻离子在促进动态醛胺形成和激活酮基以进行醇醛加成方面起着至关重要的作用。这种创新方法专门针对五元碳醛和杂环醛，涉及不寻常的醛作为供体，酮作为受体。特别是，烯醇化芳基酮醛和杂原子嵌入酮醛仅用我们的新催化剂产生环化产物，而其他催化剂主要提供自醇醛或分解产物。通过合成不同的甲醛，包括环戊烯、茚、二氢呋喃、苯并呋喃、二氢吡咯、吲哚、噻吩、二氢噻喃和苯并噻喃，证明了该方法的范围和多样性。
• Synthesis of macrolides containing an azine or hydrazide fragment via successive tishchenko disproportionation and [1 + 1]-condensation
  作者：G. Yu. Ishmuratov、G. R. Mingaleeva、M. P. Yakovleva、R. R. Muslukhov、O. O. Shakhanova、E. M. Vyrypaev、A. G. Tolstikov

  DOI：10.1134/s1070428011090259

  日期：2011.9

  Eight potentially useful 15-, 17-, 20-, and 22-25-membered macrolides having an azine or hydrazide fragment were synthesized starting from L-menthol, tetrahydropyran, and 4-methyltetrahydropyran via [1 + 1]-condensation of hydrazine hydrate and some dicarboxylic dihydrazides with 7-oxooctyl 7-oxooctanoate, 3-methyl-7-oxooctyl 3-methyl-7-oxooctanoate, and (3R)-3,7-dimethyl-6-oxooctyl (3R)-3,7-dimethyl-6-oxooctanoate obtained by the Tishchenko reaction from 7-oxo-, 3-methyl-7-oxo, and (3R)-3,7-dimethyl-6-oxooctanals, respectively.
• [EN] NOVEL CYCLIC OXYGENATED COMPOUNDS HAVING COOLING, FRAGRANCE, AND FLAVOR PROPERTIES, AND USES THEREOF<br/>[FR] NOUVEAUX COMPOSES CYCLIQUES OXYGENES POSSEDANT DES PROPRIETES DE RAFRAICHISSEMENT, DE FRAGRANCE ET DE SAVEUR, ET UTILISATIONS DESDITS COMPOSES
  申请人：AROMAGEN CORP

  公开号：WO2005049562A3

  公开（公告）日：2005-10-06