5-cyclohexyl-5-hydrofuran-2-one | 60112-29-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 5-cyclohexyl-5-hydrofuran-2-one
• 英文别名: 5-cyclohexyl-2(5H)-furanone；5-cyclohexyl-5H-furan-2-one；5-cyclohexyl-5H-furan-2-one；5-Cyclohexyl-2(5H)-furanon；2-cyclohexyl-2H-furan-5-one
• CAS: 60112-29-0
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: RKFMXRPKHIDKTO-UHFFFAOYSA-N

物化性质

• 熔点：
  73.5-75.0 °C
• 沸点：
  308.7±11.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  1-环己基-2-丙醇 在 臭氧 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 生成 5-cyclohexyl-5-hydrofuran-2-one
  参考文献：
  名称：

  从均丙醇中制备α，β-不饱和内酯的通用方法。

  摘要：

  [公式：见正文]开发了一种通过与乙酸甲酯的烯醇锂反应从β-乙酰氧基醛合成α，β-不饱和内酯的新方法。该反应对醛底物的结构变化相对不敏感。该方法扩展到由α-乙酰氧基醛合成五环内酯。获得了有关此一锅转化机制的实验证据。这些观察结果与最初的醛醇缩合与随后的酰基迁移，内酯化和β-消除而不是烯醇平衡醛醇机制有关。

  DOI：

  10.1021/ol990632u

文献信息

• DIANIONS OF β-HYDROXY SULFONES: NEW AND GENERAL APPROACH TO SELECTIVE SYNTHESIS OF 2(5<i>H</i>)-FURANONES
  作者：Kazuhiko Tanaka、Kazuhiko Ootake、Keisuke Imai、Nobuo Tanaka、Aritsune Kaji

  DOI：10.1246/cl.1983.633

  日期：1983.5.5

  electrophiles including alkyl halides, carbonyl compounds, and sodium iodoacetate. A convenient synthetic method for 4-alkyl- and 5-alkyl-2(5H)-furanones has been developed by using these dianions. A new synthetic approach to trans-3,4-bis(3-hydroxybenzyl)dihydro-2(3H)-furanone, the first lignan found in humans, via a facile reduction of 2(5H)-furanone with Mg-methanol is also decribed.

  衍生自 β-羟基砜的二价阴离子对多种亲电子试剂具有高度反应性，包括卤代烷、羰基化合物和碘乙酸钠。已经通过使用这些二价阴离子开发了一种方便的 4-烷基-和 5-烷基-2(5H)-呋喃酮合成方法。一种合成反式-3,4-双（3-羟基苄基）二氢-2（3H）-呋喃酮的新方法，这是人类发现的第一种木脂素，通过用Mg-甲醇轻松还原2（5H）-呋喃酮描述。
• DIANIONS OF<i>N</i>-MONOSUBSTITUTED-3-(PHENYLSULFONYL)PROPANAMIDES. CONVENIENT REAGENTS FOR THE SYNTHESIS OF 5-ALKYL-2(5<i>H</i>)-FURANONES
  作者：Kazuhiko Tanaka、Hisanori Wakita、Hidemi Yoda、Aritsune Kaji

  DOI：10.1246/cl.1984.1359

  日期：1984.8.5

  Treatment of N-phenyl-3-(phenylsulfonyl)propanamide with 2 equiv. of butyllithium at −78 °C afforded the dianion. Aldehydes and ketones upon treatment with the dianion provided stable γ-hydroxy amides, which were converted in good yields to 5-alkyl-2(5H)-furanones. Optically active (R)- and (S)-5-octyl-2(5H)-furanones, and (R)- and (S)-5-tridecyl-2 (5H)-furanones were prepared from aldehydes and the dianions, derived from chiral N-monosubstituted-3-(phenylsulfonyl)propanamides.

  在 -78 °C 下，用 2 等量的丁锂处理 N-苯基-3-(苯磺酰基)丙酰胺，可得到萃取物。醛和酮在与该二元离子进行处理后，可生成稳定的 γ-羟基酰胺，并以良好的产率转化为 5-烷基-2(5H)-呋喃酮。光学活性的 (R)- 和 (S)-5- 辛基-2(5H)-呋喃酮以及 (R)- 和 (S)-5- 十三烷基-2(5H)-呋喃酮是由醛和手性 N-单取代-3-(苯磺酰基)丙酰胺衍生的二元离子制备的。
• 1-Benzyloxy-3-(p-tolylsulfonyl)propene as an acrolein β-anion equivalent. Synthesis of 4-substituted 2-butenolides
  作者：Donald Craig、Christopher J. Etheridge、Alison M. Smith

  DOI：10.1016/s0040-4039(00)60211-3

  日期：1992.11

  Lithiation of 1-benzyloxy-3-(p-tolylsulfonyl)propene 6 and reaction with aldehydes give alcohols 7. Sequential hydrolysis-cyclization, oxidation and DBU-mediated elimination of dine elements of p-TolSO2H gives 4-substituted 2-butenolides 10 in good overall yield.

  1-苄氧基-3-（对甲苯磺酰基）丙烯6的锂化和与醛的反应得到醇7。通过顺序水解-环化，氧化和DBU介导的对-TolSO 2 H的二价元素消除，可得到具有良好总收率的4-取代的2-丁烯内酯10。
• Preparation and reactivity of functionalized alkenyl-zinc, -copper, and -chromium organometallics
  作者：Paul Knochel、C. Janakiram Rao

  DOI：10.1016/s0040-4020(01)80504-4

  日期：1993.1

  Beta-halogeno-alpha,beta-unsaturated carbonyl derivatives were converted to the corresponding zinc organometallics 2a under mild conditions in THF (Zn dust, 25-45-degrees-C, 1-4h). These functionalized alkenylzinc iodides react with a variety of alkenyl and aromatic iodides affording the desired coupling products in 40-97% yield. The addition of a THF solution of CuCN.2LiCl to 2a affords the corresponding organocopper derivatives 2b which react with electrophiles, such as alkynyl and allylic halides, nitro olefins, enones, and chlorotrimethylstannane providing polyfunctional unsaturated carbonyl compounds in 71-95% yield. The insertion of chromium (II) chloride to beta-iodo and to some beta-(p-tosyl)enones in DMF furnishes new functionalized chromium (III) organometallics 2c which react with aldehydes providing gamma-hydroxy unsaturated carbonyl derivatives in 40-91% yield. The synthetic scope and the limitations of this methodology are discussed.
• Trans-Selective Conversions of γ-Hydroxy-α,β-Alkynoic Esters to γ-Hydroxy-α,β-Alkenoic Esters
  作者：Christopher T. Meta、Kazunori Koide

  DOI：10.1021/ol0495366

  日期：2004.5.1

  gamma-Hydroxy-alpha,beta-acetylenic esters are used as precursors to prepare gamma-hydroxy-alpha,beta-alkenoic esters by means of trans-selective additions of two hydrogen atoms or one hydrogen atom and one iodine atom across the triple bonds. These methods allow for the preparation of beta-substituted and alpha,beta-disubstituted alkenoic esters in highly stereoselective manners.