γ-methyl decalactone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: γ-methyl decalactone
• 英文别名: (4R,5S)-5-hexyl-4-methyldihydrofuran-2(3H)-one；5-Hexyl-4-methyldihydro-2(3H)-furanone, trans-；(4R,5S)-5-hexyl-4-methyloxolan-2-one
• 化学式: C₁₁H₂₀O₂
• 分子量: 184.279
• InChiKey: XNRLAEXLQFIKEY-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-己基-4-甲基四氢呋喃-2-醇 在 NaOAc buffer 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 γ-methyl decalactone
  参考文献：
  名称：

  关于使用E -1-甲氧基甲氧基丁-2-烯基（三正丁基）锡烷作为苏式选择性的均烯酸酯等效物

  摘要：

  （E）-1-甲氧基甲氧基丁-2-烯基（三正丁基）锡烷，可通过将三正丁基锡锂加到巴豆醛中而容易获得，并用氯甲基甲基醚保护如此形成的醇，在加热下与芳族化合物反应和脂族醛得到苏--4，5-二取代丁内酯。

  DOI：

  10.1039/c39820001115

文献信息

• Enantioselective, Catalytic One‐Pot Synthesis of <i>γ</i> ‐Butyrolactone‐Based Fragrances
  作者：Ceyda Kumru、Thomas Classen、Jörg Pietruszka

  DOI：10.1002/cctc.201801040

  日期：2018.11.7

  Herein the preparative (1 g scale), stereoselective syntheses of various alkyl‐substituted γ‐butyrolactone fragrances 1 is described. The α,β‐unsaturated γ‐keto esters 2 as starting materials were synthesized by a Horner‐Wadsworth‐Emmons reaction and are further reduced by an ene reductase and alcohol dehydrogenase in a one‐pot enzyme cascade to nine desired γ‐butyrolactones 1, among them whisky (1 c)

  本文描述了各种烷基取代的γ-丁内酯香料1的制备（1 g规模）的立体选择性合成。以Horner-Wadsworth-Emmons反应合成作为原料的α，β-不饱和γ-酮酸酯2，并通过单罐酶级联反应中的烯还原酶和醇脱氢酶进一步将其还原为九种所需的γ-丁内酯1，其中威士忌（1 c）和白兰地内酯（1 d）。产品1以中等至良好的收率和非常好的非对映选择性获得了C。此外，对n Bu取代基的位置进行了置换，以研究其对酶级联反应的影响。
• An Expedient Synthesis of Olfactory Lactones by Intramolecular Hydroacylalkoxylation Reactions
  作者：Luis A. Adrio、King Kuok Mimi Hii

  DOI：10.1002/ejoc.201001556

  日期：2011.4

  available chiral precursor. By using an intramolecular hydroacylalkoxylation reaction in the final step, a correlation between the (E)/(Z) configuration of the precursor and the product distribution has been established, for the first time, in this type of cyclisation reactions.

  一系列 4,5-二取代 γ-内酯，包括威士忌和干邑白兰地内酯，是从容易获得的手性前体分四步合成的。通过在最后一步中使用分子内加氢酰烷氧基化反应，在此类环化反应中首次建立了前体的 (E)/(Z) 构型与产物分布之间的相关性。
• Solid-Support Synthesis of 1,2-Diols and <i>γ</i>-Lactones Through Addition of <i>α</i>-(Benzoyloxy)crotylindium Reagents to Aldehydes
  作者：Janine Cossy、Chrystelle Rasamison、Domingo Gomez Pardo、James A. Marshall

  DOI：10.1055/s-2001-13367

  日期：——

  A procedure for the solid phase synthesis of 1,2-diols and γ-lactones from α-(hydroxy)crotylstannane has been developed through transmetalation with InBr3. A variety of 1,2-diols and γ-lactones were synthesized in satisfactory yields and, in some cases, with excellent diastereoselectivity. The products are formed free of tin contamination.

  通过 InBr3 的金属转移，开发了从 α-（羟基）巴豆基锡烷固相合成 1,2-二醇和 γ-内酯的方法。各种1,2-二醇和γ-内酯的合成都具有令人满意的产率，并且在某些情况下具有优异的非对映选择性。产品不含锡污染。
• On the use of E-1-methoxymethoxybut-2-enyl(tri-n-butyl)stannane as a threo-selective, homo-enolate equivalent
  作者：Andrew J. Pratt、Eric J. Thomas

  DOI：10.1039/c39820001115

  日期：——

  (E)-1-Methoxymethoxybut-2-enyl(tri-n-butyl)stannane, readily available by addition of tri-n-butylstannyllithium to crotonaldehyde, and protection of the alcohol so formed using chloromethyl methyl ether, reacts on heating with aromatic and aliphatic aldehydes to give threo-4,5-disubstituted butyrolactones.

  （E）-1-甲氧基甲氧基丁-2-烯基（三正丁基）锡烷，可通过将三正丁基锡锂加到巴豆醛中而容易获得，并用氯甲基甲基醚保护如此形成的醇，在加热下与芳族化合物反应和脂族醛得到苏--4，5-二取代丁内酯。
• Composition for odour improvement
  申请人：Symrise AG

  公开号：US11332692B2

  公开（公告）日：2022-05-17

  The invention relates to a preparation containing: (i) a composition containing (a) one, two or a plurality of compounds selected from the group consisting of (a1) alcohol monoterpenes of formula (I) in which R1 is H or methyl, R2 is H or C2-alkenyl, und R3 is a linear or branched, saturated or unsaturated hydrocarbon radical with 4 to 10 carbon atoms, and the enantiomers, diastereomers, racemates, solvates and physiologically compatible salts thereof, and/or (a2) bicyclic epoxy-monoterpenes, (b) at least two lactones of formula (II) in which R4 is H or methyl, R5 is a linear or branched, saturated or unsaturated hydrocarbon radical with 2 to 10 hydrocarbon atoms and n is the number 1 or 2, and the enantiomers, diastereomers and racemates thereof, (c) one, two or a plurality of solvents selected from the group consisting of ethanol, water, dipropylene glycol (DPG), diethyl phtalate (DEP), propylene glycol (PG), isopropyl myristate (IPM), isopropyl palmitate (IPP), triethyl citrate (TEC), triacetin (TRI), 1,2-Propanediol, 1,3-Propanediol, Propanethiol, Pentanediol, Hexanediol, Octanediol, Decanediol (SymClariol®), Dodecanol, 4-hydroxy-acetophenone (SymSave® H), glycerine, butylene glycol, pentylene glycol, hexylene glycol, decylene glycol, propylene carbonate, butylene carbonate, glycerine carbonate, 2-5 benzyl heptanol, lauryl alcohol, trimethyl-hydroxypentyl-isobutyrate, glyceryl-caprylate, ethylhexyl glycerine, benzyl benzoate (BB), and optionally (d) other flavouring agents or aromatic substances selected from the group consisting of 3-phenylbutanal (Trifernal), acetyl methyl carbinol, anethole, anisyl acetate, dihydroeugenol, linalyl formate, 2-methyldecanal, 2-benzyl-2-methylbut-3-ene nitrile (Ci-Trowanil® B), 3-hexenyl acetate, styrallyl acetate, belanis, citronellal, cinnamyl acetate, rhubafuran, beta-ions, anther, prenyl acetate, 2-phenyl propanal, 4-(4-hydroxyphenyl)butan-2-one (Frambinon®), ethyl phenoxyacetate, isoralderine, gamma-terpinene, limonene, neocyclocitral, methyl lavender ketone, styrallyl propionate, phenyl ethyl propionate, limonenal, 4-isopentylcyclohexanol (Symrose®), 4-methyl-2-phenyl-3,6-dihydro-2H-pyran/4-methylene-2-phenyl-tetrahydropyrane (Rosyrane super), hydrocitronitril, phenoxanol, isoamyl phenylacetate, damascone, silvial, nectaryl, ambroxide, acetyl pyrazine, trimethyl pyrazine, isoamyl acetate, para-cresyl methyl ether, filbertone, cyclohexyl acetate, heliotropin, acetophenone, anisaldehyde, para-methyl acetophenone, veratraldehyde, methyl anisate and vertoprenal; (ii) aldehydes of formula (III) in which R6 is a saturated or non-saturated, linear hydrocarbon radical; and/or (iii) free fatty acids of formula (IV), in which R7 is a linear or branched, saturated hydrocarbon radical.

  本发明涉及一种含有以下成分的制剂(i) 含有(a)一种、两种或多种选自以下组别的化合物的组合物 (a1)式(I)醇单萜烯，其中 R1 是 H 或甲基，R2 是 H 或 C2-烯基，und R3 是具有 4 至 10 个碳原子的线性或支链、饱和或不饱和烃基，以及其对映体、非对映体、外消旋体、溶物和生理相容盐，和/或 (a2)双环环氧单萜烯、(a2) 双环环氧单萜，(b) 至少两个式（II）的内酯，其中 R4 是 H 或甲基，R5 是具有 2 至 10 个碳原子的线性或支链饱和或不饱和烃基，n 是数字 1 或 2、及其对映体、非对映体和外消旋体， (c) 一种、两种或多种溶剂，选自乙醇、水、二丙二醇（DPG）、乙酸二乙酯 （DEP）、丙二醇（PG）、肉豆蔻酸异丙酯（IPM）、棕榈酸异丙酯（IPP）、 柠檬酸三乙酯（TEC）组成的溶剂组、三醋精（TRI）、1,2-丙二醇、1,3-丙二醇、丙硫醇、戊二醇、己二醇、辛二醇、癸二醇（SymClariol®）、十二醇、4-羟基苯乙酮（SymSave® H）、甘油、丁二醇、戊二醇、己二醇、癸二醇、碳酸丙烯酯、碳酸丁烯酯、碳酸甘油酯、2-5-苄基庚醇、月桂醇、三甲基羟基戊基异丁酸酯、丙烯酸甘油酯、乙基己基甘油酯、苯甲酸苄酯 (BB)，以及可选的 (d) 其他调味剂或芳香物质，选自 3-苯基丁醛（Trifernal）、乙酰甲基甲醇茴香醚、乙酸茴香酯、二氢丁香酚、甲酸芳樟酯、2-甲基癸醛、2-苄基-2-甲基丁-3-烯腈（Ci-Trowanil® B）、乙酸 3-己烯酯、乙酸苯乙烯烯酯、香茅醛、乙酸肉桂酯、呋喃西林、β-离子、花药、乙酸炔丙酯、2-苯基丙醛、4-（4-羟基苯基）丁-2-酮（Frambinon®）、苯氧乙酸乙酯、异橙皮醚、γ-萜品烯、柠檬烯、新环柠檬醛、甲基薰衣草酮、丙酸苯乙烯酯、丙酸苯乙酯、柠檬烯醛、4-异戊基环己醇（Symrose®）、4-甲基-2-苯基-3,6-二氢-2H-吡喃/4-亚甲基-2-苯基-四氢吡喃（Rosyrane super）、氢化硝基甲苯、phenoxanol, isoamyl phenylacetate, damascone, silvial, nectaryl, ambroxide, acetyl pyrazine, trimethyl pyrazine, isoamyl acetate, para-cresyl methyl ether, filbertone, cyclohexyl acetate, heliotropin, acetophenone, anisaldehyde, para-methyl acetophenone, veratraldehyde, methyl anisate and vertoprenal；(ii) 式（III）中 R6 为饱和或非饱和线性烃基的醛类；和/或 (iii) 式（IV）中 R7 为线性或支链饱和烃基的游离脂肪酸。