(5R)-4-甲基-5-[[(1R,2S,5R)-5-甲基-2-(1-甲基乙基)环己基]氧基]-2-(5H)-呋喃酮 | 120262-97-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: (5R)-4-甲基-5-[[(1R,2S,5R)-5-甲基-2-(1-甲基乙基)环己基]氧基]-2-(5H)-呋喃酮
• 英文名称: 5-menthyloxy-4-methyl-2<5H>-furanone
• 英文别名: (5R)-5-(l-menthyloxy)-4-methyl-2(5H)-furanone；3-methyl-4-(L-menthyloxy)but-2-en-1,4-olide；4-methyl-5-(R)-menthyloxy-2(5H)-furanone；(2R)-3-methyl-2-[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]oxy-2H-furan-5-one
• CAS: 120262-97-7；120263-06-1；120263-07-2；120262-96-6
• 化学式: C₁₅H₂₄O₃
• 分子量: 252.354
• InChiKey: AUMJJCYIXFXSQM-CQROYNQRSA-N

物化性质

• 沸点：
  377.2±37.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5R)-4-甲基-5-[[(1R,2S,5R)-5-甲基-2-(1-甲基乙基)环己基]氧基]-2-(5H)-呋喃酮 在 sodium tetrahydroborate 、 三溴化硼 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 1.25h， 生成 3-[(1S,2S)-1-hydroxy-2-methylbutyl]-4-methylfuran-2(5H)-one
  参考文献：
  名称：

  Bioactive butenolides from Streptomyces antibioticus TÜ 99: absolute configurations and synthesis of analogs

  摘要：

  The four furanones (butenolides) 1-4, which had been isolated from the fermentation broth of Streptomyces antibioticus TU 99 and in preliminary tests had been shown to be biologically active, were synthesized by reaction of the readily available furanones 9 or 16 with 2-methylpropanal or 2-methylbutanal. In addition, a series of analogs was prepared in a similar way from 16 using different aldehydes. The hitherto unknown absolute configurations of the natural products 1-4 as well as those of all the analogs prepared were determined with Mosher's NMR method and/or X-ray crystallography. Some of the compounds synthesized proved to be active in the quorum sensing system of Chromobacterium violaceum. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00483-6
• 作为产物：
  描述：

  2a(S)5a(S)6(R)-3,4-diaza-6-menthyloxy-1-oxa-2-oxo-bicyclo<3.3.0>oct-3-ene 以 甲苯 为溶剂， 反应 12.0h， 以100%的产率得到(5R)-4-甲基-5-[[(1R,2S,5R)-5-甲基-2-(1-甲基乙基)环己基]氧基]-2-(5H)-呋喃酮
  参考文献：
  名称：

  Asymmetric 1,3-dipolar cycloadditions to 5-(R)-menthyloxy-2(5H)-furanone

  摘要：

  Various diazo compounds, nitrile oxides, nitrones and azomethine ylides were examined in 1,3-dipolar cycloadditions to enantiomerically pure 5-(R)-menthyloxy-2(5H)-furanone 1a. Pyrazoline 9 was obtained in 100% c.y. as a mixture of 2 diastereoisomers in ratios up to 72 : 28, whereas pyrazoline 16 was obtained in 100% c.y. as a single enantiomer. Photochemically pyrazolines 9 and 10 have been converted to cyclopropanes 11 and 13. Under thermal conditions pyrazoline 9 is converted to 4-methyl-5-menthyloxy-2(5H)-furanone. Isoxazoles 21a-24a were obtained enantiomerically pure via nitrile oxide addition to la in 64-67% yield. Nitrone addition afforded isoxazolidines 27, 28 and 34 with complete anti-facial- and regiochemistry, but with endo-exo selectivities up to 76%. Enantiomerically pure isoxazolidines were obtained in 25-75% yield. Pyrrolidine 36 was obtained diastereomerically pure in 81% c.y. Pyrrolidines 42 and 45, however, were obtained as diastereomeric mixtures in 37% resp. 6% yield.

  DOI：

  10.1016/0957-4166(94)80023-5

文献信息

• The Butenolide Signaling Molecules SRB1 and SRB2 Induce Lankacidin and Lankamycin Production in Streptomyces rochei
  作者：Kenji Arakawa、Naoto Tsuda、Akihiro Taniguchi、Haruyasu Kinashi

  DOI：10.1002/cbic.201200149

  日期：2012.7.9

  Control of antibiotic production: Two signaling molecules—SRB1 and SRB2—that induce production of lankacidin and lankamycin in Streptomyces rochei 7434AN4 were isolated and their structures were determined. Each contains a 2,3‐disubstituted γ‐hydroxybutenolide skeleton, and the stereochemistry at C‐1′ is crucial for inducing activity.

  抗生素生产的控制：分离出两个诱导罗氏链霉菌7434AN4中兰卡霉素和兰卡霉素产生的信号分子SRB1和SRB2，并确定了它们的结构。每个都包含一个2,3-二取代的γ-羟基丁烯内酯骨架，C-1'处的立体化学对于诱导活性至关重要。
• Asymmetric synthesis of carbocycles: use of intramolecular conjugate displacement
  作者：Dinesh T. Sreedharan、Derrick L. J. Clive

  DOI：10.1039/c3ob40115d

  日期：——

  Intramolecular conjugate displacement (ICD), the process illustrated in eqn (1), has been applied to the Morita–Baylis–Hillman adducts formed from (5S)-5-(L-menthyloxy)-2(5H)-furanone and aldehydes that are substituted in the γ- or δ-position by geminal phenylthio groups. When the initial Morita–Baylis–Hillman alcohols are acetylated and oxidized to geminal sulfones, deprotonation causes ring closure

  分子内共轭置换（ICD），过程说明如下 eqn（1），已被应用于Morita-Baylis-Hillman加成物，由 （5 S）-5-（L-薄荷氧基）-2（5 H）-呋喃酮和在γ或δ位被双苯硫基取代的醛。当最初的Morita–Baylis–Hillman醇被乙酰化并氧化为双砜时，去质子化会导致ICD闭环（2.5→2.6）。氢化，DIBAL-H还原和去磺酰化释放出光学上纯净的碳环。
• Synthetic Access to Biologically Active Butenolides from <i>Streptomyces antibioticus</i>
  作者：Gilles Grossmann、Urs Séquin

  DOI：10.1055/s-2001-10760

  日期：——

  A synthetic route to a class of substituted butenolides isolated from Streptomyces antibioticus has been elaborated. The process involves coupling of the readily available methylated furanone 5 with aldehydes.

  已经详细阐述了从抗生素链霉菌中分离出的一类取代的丁烯内酯的合成路线。该过程涉及容易获得的甲基化呋喃酮 5 与醛的偶联。
• Asymmetric 1,3-dipolar cycloadditions to 5-menthyloxy-2[5H]-furanones.
  作者：Ben de Lange、Ben L. Feringa

  DOI：10.1016/s0040-4039(00)80747-9

  日期：1988.1
• Synthesis of enantiomerically pure .gamma.-(menthyloxy)butenolides and (R)- and (S)-2-methyl-1,4-butanediol
  作者：Ben L. Feringa、Ben De Lange、Johannes C. De Jong

  DOI：10.1021/jo00271a050

  日期：1989.5