1-hydroxynonan-2-one | 1072-08-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1-hydroxynonan-2-one
• 英文别名: 1-hydroxy-2-nonanone
• CAS: 1072-08-8
• 化学式: C₉H₁₈O₂
• 分子量: 158.241
• InChiKey: MIBPMIMLABIQGY-UHFFFAOYSA-N

物化性质

• 熔点：
  34-35 °C
• 沸点：
  96 °C(Press: 16 Torr)
• 密度：
  0.921±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  1-hydroxynonan-2-one 在 正丁基锂 、 碘 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 7.17h， 生成 4-heptyl-3-iodofuran-2(5H)-one
  参考文献：
  名称：

  乙炔炔二醇的亲电碘环化合成取代的3-碘香豆素和3-碘代丁烯内酯

  摘要：

  各种4-取代的3- iodocoumarins和的一种方便和一般合成4,5-二取代的3- iodobutenolides经由异6-描述内切-挖iodocyclization的3-乙氧基-1-（2-烷氧基苯基）-2-炔1-烷氧基-4-乙氧基-3-yn-1,2-二醇的1-ols和5- endo - dig碘环化。该反应在非常温和的条件下使用I 2在CH 2 Cl 2中或在室温下于甲苯中进行。OMe和OMOM组中的氧气被用作分子内环化的有效亲核试剂，从而以良好或优异的收率获得了产物。

  DOI：

  10.1021/jo400499r
• 作为产物：
  描述：

  2-壬酮 在 四氧化锇 水 、 N-甲基吗啉氧化物 、 lithium diisopropyl amide 作用下， 生成 1-hydroxynonan-2-one
  参考文献：
  名称：

  酮的α-羟基氧化作用：四氧化O / N-甲基吗啉-N-氧化物氧化甲硅烷基烯醇醚

  摘要：

  甲硅烷基烯醇醚的四氧化s / N-甲基吗啉-N-氧化物氧化反应是通过动力学或热力学区域化学控制的方式从酮中衍生出来的，可产生高至优异收率的α-酮醇。

  DOI：

  10.1016/s0040-4039(01)92501-8

文献信息

• Studies on hypolipidemic agents. II Synthesis of 1-arenesulfonyloxy-2-alkanone derivatives as potent esterase inhibitors and hypolipidemic agents.
  作者：KAZUO OGAWA、TADAFUMI TERADA、YOSHIYUKI MURANAKA、TOSHIHIRO HAMAKAWA、SADAO HASHIMOTO、SETSURO FUJII

  DOI：10.1248/cpb.34.3252

  日期：——

  Many 2-oxoalkyl arenesulfonate derivatives having straight or branched alkyl chains of different lengths, 2-oxoalkyl bis-arenesulfonate derivatives, and alkyl arenesulfonate derivatives having a ketal moiety at the 2-position on the alkyl chain were synthesized, and their esterase-inhibitory activities, as well as hypolipidemic activities, were evaluated.Among these compounds, 1-(2, 4, 6-trimethylbenzenesulfonyloxy)-2-dodecanone (III-1u), and 1-(2, 3, 4, 6-tetramethylbenzenesulfonyloxy)-2-hexanone (III-1w), -2-octanone (III-1x) and -2-decanone (III-1y) exhibited potent esterase-inhibitory activities (IC50=3×10-10, 2×10-10, 2×10<-10> and 3×<-11>M, respectively). However, the sulfonate (XV) having a ketal moiety on the alkyl chain and the bis-sulfonate (XVI) exhibited low inhibitory activities toward esterase in comparison with III and XII. Most of the compounds III and some of the compounds XII exhibited potent hypolipidemic activities corresponding to more than 50% lipid-lowering effect (plasma triglyceride and cholesterol ester) in vivo. The structure-activity relatioinships of these compounds are discussed.

  合成了许多具有直链或支链不同长度烷基链的2-氧代烷基芳磺酸盐衍生物、2-氧代烷基双芳磺酸盐衍生物以及在烷基链的2-位具有缩酮部分的烷基芳磺酸盐衍生物，并评估了它们的酯酶抑制活性及降血脂活性。在这些化合物中，1-(2,4,6-三甲基苯磺酰氧基)-2-十二烷酮（III-1u）、1-(2,3,4,6-四甲基苯磺酰氧基)-2-己烷酮（III-1w）、-2-辛烷酮（III-1x）和-2-癸烷酮（III-1y）表现出强效的酯酶抑制活性（IC50分别为3×10-10、2×10-10、2×10-10和3×10-11M）。然而，相对于III和XII，具有烷基链上缩酮部分的磺酸盐（XV）和双磺酸盐（XVI）对酯酶的抑制活性较低。大多数化合物III和部分化合物XII表现出强效的降血脂活性，对应于体内超过50%的脂质降低效果（血浆甘油三酯和胆固醇酯）。讨论了这些化合物的构效关系。
• [EN] PROCESS FOR PRODUCING ALPHA-HYDROXYKETONE COMPOUND<br/>[FR] PROCÉDÉ DE PRODUCTION DE COMPOSÉ ALPHA-HYDROXYCÉTONE
  申请人：SUMITOMO CHEMICAL CO

  公开号：WO2013157651A1

  公开（公告）日：2013-10-24

  An object of the present invention is to provide a new process for producing an α-hydroxyketone compound. The present invention relates to a process for producing an α-hydroxyketone compound comprising mixing at least hydrophobic solvent selected from the group consisting of an aromatic hydrocarbon solvent, an aliphatic hydrocarbon solvent, a halo-hydrocarbon solvent, and an ether solvent incompatible with water, a compound defined by the formula (1) wherein, R1 and R2 are each independently a hydrogen atom, an optionally substituted alkyl group; R3 is an optionally substituted alkyl group or an aryl group; and X- is an anion, a basic compound, formalin, and an aldehyde compound with 2 to 30 carbon atoms.

  本发明的一个目的是提供一种生产α-羟基酮化合物的新工艺。本发明涉及一种生产α-羟基酮化合物的工艺，包括将至少选择自芳香烃溶剂、脂肪烃溶剂、卤代烃溶剂和与水不相容的醚溶剂的疏水性溶剂，与化学式（1）所定义的化合物混合，其中，R1和R2各自独立地是氢原子、可选择取代的烷基团；R3是可选择取代的烷基团或芳基团；X-是阴离子、碱性化合物、甲醛和碳原子数为2到30的醛化合物。
• Asymmetric Synthesis of <i>N</i> ‐Substituted 1,2‐Amino Alcohols from Simple Aldehydes and Amines by One‐Pot Sequential Enzymatic Hydroxymethylation and Asymmetric Reductive Amination
  作者：Yu Li、Na Hu、Zefei Xu、Yunfeng Cui、Jinhui Feng、Peiyuan Yao、Qiaqing Wu、Dunming Zhu、Yanhe Ma

  DOI：10.1002/anie.202116344

  日期：2022.4.19

  A one-pot, two-step enzymatic cascade reaction was developed for the synthesis of N-substituted chiral 1,2-amino alcohols from simple aldehydes and amines by coupling hydroxymethylation and reduction amination reactions. This methodology was then applied to rapidly access a key building block of various tetrahydroquinoline alkaloids of pharmaceutical importance.

  开发了一种一锅两步酶级联反应，通过偶联羟甲基化和还原胺化反应，由简单的醛和胺合成N-取代的手性 1,2-氨基醇。然后将该方法应用于快速获取具有药学重要性的各种四氢喹啉生物碱的关键组成部分。
• Preparation of alpha-hydroxy ketones via carbene-catalyzed umpolung reaction of aldehydes
  申请人：Jackstell Ralf

  公开号：US20080051608A1

  公开（公告）日：2008-02-28

  The present invention relates to the preparation of α-hydroxy ketones of the general formula I. In particular, the invention relates to novel imidazolinium carboxylate adducts and to a novel process for using catalytic amounts of imidazolium and imidazolinium carboxylate adducts in the acyloin reaction of aldehydes to prepare hydroxy ketones of the general formula I, where R and R′ are the same or different and are each H or a straight-chain or branched and optionally substituted C 1 -C 12 -alkyl radical, and R″═H 3 CSCH 2 CH 2 , t-butyl, n-butyl, sec-butyl, n-propyl, i-propyl, an optionally heteroatom-substituted C 6 -C 18 -aryl, heteroaryl, C 6 -C 18 -arylalkyl, especially phenylmethyl, where phenyl may again be heteroatom-substituted, or heteroalkyl.

  本发明涉及通式I的α-羟基酮的制备。特别是，本发明涉及新型咪唑啉酮酸盐加合物以及一种新的过程，该过程利用咪唑和咪唑啉酮酸盐加合物的催化量在醛的酰乙醇反应中制备通式I的羟基酮，其中R和R′相同或不同，每个都是H或直链或支链且可选择取代的C1-C12烷基基团，而R″=H3CSCH2CH2、叔丁基、正丁基、异丁基、正丙基、异丙基、可选择杂原子取代的C6-C18芳基、杂原子芳基、C6-C18芳基烷基，特别是苯甲基，其中苯可能再次被杂原子取代，或者杂原子烷基。
• Novel derivatives of bio-affecting phenolic compounds and pharmaceutical composition containing them
  申请人：INTERx RESEARCH CORPORATION

  公开号：EP0046270A1

  公开（公告）日：1982-02-24

  Novel transient prodrug forms of bio-affecting phenolic compounds are selected from the group consisting of those having the structural formula (I): wherein X is O, S or NR5 wherein R5 is hydrogen or lower alkyl; R1 is the mono- or polydehydroxylated residue of a non-steroidal bio-affecting phenol, with the proviso that R' is other than a monohydroxylated or didehydroxylated residue of a phenolic, nuclear dihydroxy natural sympathetic or sympathomimetic amine; R2 is selected from the group consisting of straight or branched chain alkyl, aryl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, aralkyl, alkaryl, aralkenyl, aralkynyl, alkenylaryl, alkynylaryl, (lower acyloxy)alkyl, and carboxyalkyl; 3- to 8-membered, saturated or unsaturated mono-heterocyclic or polyheterocyclic containing from 1 to 3 of any one or more of the heteroatoms N, S or O; and mono- or polysubstituted derivatives of the above; R3 is hydrogen, lower acyl, cyano, halo(lower alkyl), carbamyl, lower alkylcarbamyl, di(lower alkyl)carbamyl, CH2ONO2, -CH2OCOR2 or any non-heterocyclic member of the group defined by R2 above; and n is at least one and equals the total number of phenolic hydroxyl functions comprising the non-steroidal bioaffecting phenol etherified via a R2COXCH(R3)0-moiety; those having the structural formula (II): wherein X, R', R2 and R3 are as defined above, and n and m are each at least one and the sum of n+m equals the total number of phenolic hydroxyl functions comprising the non-steroidal bioaffecting phenol either etherified via a R2COXCH(R3)0-moiety or esterified via a R2COO-moiety; and the pharmaceutically acceptable acid addition salts, quaternary ammonium salts and N-oxides thereof.

  生物效应酚类化合物的新型瞬效原药形式选自具有结构式(I)的化合物组成的组： 其中 X 是 O、S 或 NR5，其中 R5 是氢或低级烷基；R1 是非类固醇生物效应酚的单羟基或多羟基残基，但 R' 不是酚、核二羟基天然交感胺或拟交感胺的单羟基或双羟基残基；R2 选自直链或支链烷基、芳基、环烷基、烯基、环烯基、炔基、芳烷基、烷芳基、芳烯基、芳炔基、烯芳基、炔芳基、（低级酰氧基）烷基和羧基烷基组成的组；R3 是氢、低级酰基、氰基、卤代（低级烷基）、氨甲酰基、低级烷基氨甲酰 基、二（低级烷基）氨甲酰基、CH2ONO2、-CH2OCOR2 或上述 R2 定义的基团中的任何非杂环成员；且 n 至少为 1，等于通过 R2COXCH(R3)0 子代醚化的非甾体生物作用酚所包含的酚羟基官能团的总数；具有结构式（II）的酚羟基官能团： 其中 X、R'、R2 和 R3 如上文所定义，n 和 m 至少各为 1，且 n+m 之和等于非甾体类生物效应酚通过 R2COXCH(R3)0 子键醚化或通过 R2COO 子键酯化的酚羟基官能团的总数；及其药学上可接受的酸加成盐、季铵盐和 N-氧化物。