环己基-羟基-乙醛 | 38559-29-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 环己基-羟基-乙醛
• 英文名称: α-Cyclohexyl-glykolaldehyd
• 英文别名: cyclohexyl-hydroxy-acetaldehyde；1-formyl-1-hydroxymethylcyclohexane；Cyclohexylketol；2-cyclohexyl-2-hydroxyacetaldehyde
• CAS: 38559-29-4
• 化学式: C₈H₁₄O₂
• 分子量: 142.198
• InChiKey: GPICSMAPTRXDOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  环己基-羟基-乙醛 在 indium 、 对甲苯磺酸 作用下， 以 水 为溶剂， 反应 11.0h， 生成 (4S,5R)-4-Allyl-5-cyclohexyl-2,2-dimethyl-[1,3]dioxolane
  参考文献：
  名称：

  Addition of Allylindium Reagents to Aldehydes Substituted at C_α or C_β with Heteroatomic Functional Groups. Analysis of the Modulation in Diastereoselectivity Attainable in Aqueous, Organic, and Mixed Solvent Systems

  摘要：

  The stereochemical course of indium-promoted allylations to alpha- and beta-oxy aldehydes has been investigated in solvents ranging from anhydrous THF to pure H2O. The free hydroxyl derivatives react with excellent diastereofacial control to give significantly heightened levels of syn-1,2-diols and anti-1,3-diols. Relative reactivities were determined in the alpha-series, and the hydroxy aldehyde proved to be the most reactive substrate. This reactivity ordering suggests that the selectivity stems from chelated intermediates. The rate acceleration observed in water can be heightened by initial acidification. Indeed, the indium-promoted allylation reaction mixtures become increasingly acidic on their own. Preliminary attention has been accorded to salt effects, and tetraethylammonium bromide was found to exhibit a positive synergistic effect on product distribution. Finally, mechanistic considerations are presented in order to allow for assessment of the status of these unprecedented developments at this stage of advancement of the field.

  DOI：

  10.1021/ja953682c
• 作为产物：
  描述：

  环己烷基甲醛 在 sodium hydroxide 、 聚合甲醛 作用下， 以 甲醇 为溶剂， 以51%的产率得到环己基-羟基-乙醛
  参考文献：
  名称：

  Azaspiro compounds

  摘要：

  这项发明涉及一种使用从以下式中选择的化合物的方法：其中R.sup.1是氢、烷基或烯基；R.sup.2是氢、烷基、环烷基或单核芳基或者R.sup.1和R.sup.2连同它们连接的碳原子形成环烷基或环烷氧基烷；R.sup.3是羟基、烷基、烷氧羰基、羟基较低烷基或者具有以下式的基团：--C(.dbd.Y)NR.sup.4 R.sup.5其中R.sup.4是氢、烷基或烯基，R.sup.5是烷基、烯基羰氧基烷或单核芳基，或者R.sup.4和R.sup.5可能与它们连接的氮原子结合形成具有1到3个杂原子的5到7成员杂环的环；Y是O或S；X是烷基、烷氧羰基烷或氰基；m是0到2的整数，n和n'是每个具有1到2值的整数，虚线表示可选的碳到碳双键，含有所述化合物作为防虫剂的组合物以及新化合物。

  公开号：

  US04400512A1

文献信息

• COMPOSITIONS AND METHODS FOR THE TREATMENT OF PATHOLOGICAL CONDITION(S) RELATED TO GPR35 AND/OR GPR35-HERG COMPLEX
  申请人：Deng Huayun

  公开号：US20120022116A1

  公开（公告）日：2012-01-26

  Disclosed are compositions and methods for the prevention and/or treatment of diseases which are pathophysiologically related to GPR35, and/or GPR35-hERG signaling complex. For example, disclosed are compounds for preventing and/or treating diseases which are pathophysiologically related to GPR35 in a subject. The compounds having a formula (I), (II) or (III):

  揭示了与GPR35及/或GPR35-hERG信号复合物在病理生理上相关的疾病的预防和/或治疗的组合物和方法。例如，揭示了用于预防和/或治疗与GPR35在受试者中病理生理相关的疾病的化合物。这些化合物具有以下公式(I)、(II)或(III)：
• [EN] METHOD FOR PRODUCING ALPHA-KETOALDEHYDE COMPOUND<br/>[FR] PROCÉDÉ DE PRODUCTION D'UN COMPOSÉ D'ALPHA-CÉTOALDÉHYDE
  申请人：SUMITOMO CHEMICAL CO

  公开号：WO2013018626A1

  公开（公告）日：2013-02-07

  An object of the present invention is to provide a new method for producing an ALPHA-ketoaldehyde compound from a 2-oxo-primary alcohol compound. The present invention provides a method for producing an ALPHA-ketoaldehyde compound including a step of oxidizing a 2-oxo-primary alcohol compound in the presence of platinum, a platinum compound, iron or an iron compound. The 2-oxo-primary alcohol compound is preferably a compound represented by the formula (1a), and the ALPHA-ketoaldehyde compound is preferably a compound represented by the formula (2a), wherein Ra is a C1-C6 alkyl group which may have a substituent or a C6-C20 aryl group which may have a substituent.

  本发明的一个目的是提供一种从2-氧代初级醇化合物制备ALPHA-酮醛化合物的新方法。本发明提供了一种制备ALPHA-酮醛化合物的方法，包括在铂、铂化合物、铁或铁化合物存在下氧化2-氧代初级醇化合物的步骤。2-氧代初级醇化合物最好是由式（1a）表示的化合物，而ALPHA-酮醛化合物最好是由式（2a）表示的化合物，其中Ra是一个可能带有取代基的C1-C6烷基基团或可能带有取代基的C6-C20芳基基团。
• A Novel Approach to γ-Hydroxy-α,β-unsaturated Compounds
  作者：Henryk Krawczyk、Katarzyna Wąsek、Jacek Kędzia

  DOI：10.1055/s-0028-1083162

  日期：——

  A simple synthesis of (E)-alk-1-enyl mesylates from (E)-alk-1-enylphosphonates is reported. Construction of γ-hydroxy-α,β-unsaturated compounds was achieved by a two-step process involving dihydroxylation of the enol mesylates followed by HWE reaction of the resulting α-hydroxy aldehydes with activated methylphosphonates. Enantioselective synthesis of the title compounds is also reported.

  报告了一种从(E)-alk-1-烯基膦酸盐简单合成(E)-alk-1-烯基甲磺酸酯的方法。通过烯醇甲磺酸酯的二羟基化，然后将得到的δ-羟基醛与活化的甲基膦酸盐进行 HWE 反应，分两步合成了δ-羟基δ,δ-不饱和化合物。报告还介绍了标题化合物的对映选择性合成。
• Zur Kenntnis der TTC-Reaktion von α-Ketolsteroiden. 4. Mitt. Umsetzung von α-Ketol-Tautomeren
  作者：H. Möhrle、D. Schittenhelm、E. Federolf

  DOI：10.1002/ardp.19723050805

  日期：——

  Die Darstellung von α‐Hydroxyaldehyden und α‐Acetoxyaldehyden als Modellsubstanzen für die Dehydrierung mit Triphenyltetrazoliumchlorid wird beschrieben. Während α‐Hydroxyaldehyde mit TTC infolge Dimerisierung fast nicht reagieren, liefern α‐Acetoxyaldehyde ein Säuregemisch. Aufgrund der Ergebnisse wird ein Mechanismus für die Reaktion vorgeschlagen.

  描述了 α-羟基醛和 α-乙酰氧基醛作为与三苯基四唑氯化物脱氢的模型物质的制备。虽然α-羟基醛由于二聚作用几乎不与TTC反应，但α-乙酰氧基醛会产生酸的混合物。根据结果​​提出了反应机理。
• Antianaphylactic agents. 1. 2-(Acylamino)oxazoles
  作者：W. J. Ross、R. G. Harrison、M. R. J. Jolley、M. C. Neville、A. Todd、J. P. Verge、W. Dawson、W. J. F. Sweatman

  DOI：10.1021/jm00190a011

  日期：1979.4

  The synthesis and biological properties of 35 2-(acylamino)oxazoles are described. The majority of the compounds inhibit the release of slow-reacting substance of anaphylaxis (SRS-A) in vitro from sensitized guinea pig chopped lung. In addition, several of the compounds inhibited the release of SRS-A from passively sensitized human chopped lung and protected guinea pigs from the effects of anaphylaxis in a modified Herxheimer test.