4-methyl-5-cyclohexyl-2-tetrahydrofuranone | 16466-27-6

• 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: 4-methyl-5-cyclohexyl-2-tetrahydrofuranone
• 英文别名: 4-methyl-1-oxa-spiro[4.5]decan-2-one；4-Methyl-1-oxaspiro[4.5]decan-2-one
• CAS: 16466-27-6
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: ZBRDYTZLDRKNRS-UHFFFAOYSA-N

物化性质

• 沸点：
  138-140 °C(Press: 10 Torr)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-methyl-5-cyclohexyl-2-tetrahydrofuranone 在 甲烷磺酸 、 phosphorus pentoxide 作用下， 以94%的产率得到2,3,4,5,6,7-六氢-3-甲基茚-1-酮
  参考文献：
  名称：

  Three carbon annelation reagents: unsaturated alpha aminonitriles as homoenolate equivalents

  摘要：

  DOI：

  10.1016/s0040-4039(00)71371-2
• 作为产物：
  描述：

  原白头翁素 在 palladium on activated charcoal 氢气 、 对苯二酚 作用下， 以 乙醚 为溶剂， -20.0~155.0 ℃ 、202.65 kPa 条件下， 反应 4.5h， 生成 4-methyl-5-cyclohexyl-2-tetrahydrofuranone
  参考文献：
  名称：

  General synthesis of 1-oxaspiro[4.5]decan-2-ones and 1-oxaspiro[4.5]decanes from 5-methylene-2(5H)-furanone

  摘要：

  5-Methylene-2(5H)-furanone underwent Diels-Alder cycloadditions to butadiene and several acyclic and cyclic C-substituted dienes, respectively, affording bicyclic and tricyclic spiroadducts in good yields. These compounds are precursors of other unsaturated and saturated spirolactones and also spiroethers, which were obtained through simple chemical reactions, i.e., hydrogenation of C-C double bonds, reduction of the carbonyl group, and Michael addition. The synthesis of 32 spirolactones and eight spiroethers illustrates the scope and efficiency of this method. Many of these products are suitable for use as components of perfumes and aromas owing to their olfactive properties.

  DOI：

  10.1021/jo00019a019

文献信息

• A new coupling reaction between β-lactones and electrophiles mediated by a system
  作者：Fouzia Machrouhi、Jean-Louis Namy

  DOI：10.1016/s0040-4020(98)00651-6

  日期：1998.9

  β-lactones react with ketones aldehydes and imines in the presence of a system to afford substituted tetrahydrofuranones and pyrrolidinones.

  在系统存在下，β-内酯与酮醛和亚胺反应，得到取代的四氢呋喃酮和吡咯烷酮。
• Novel pyrrolidine compound and a process for preparing the same
  申请人：Moritani Yasunori

  公开号：US20070167440A1

  公开（公告）日：2007-07-19

  The present invention relates to a novel pyrrolidine compound, which has a potent antagonistic activity against central cannabinoid (CB1) receptor, having the formula [I]: wherein each of R 1 and R 2 is (A) optionally substituted aryl (or heteroaryl) group, or (B) both of the groups combine to form a group of the formula: one of R 3 and R 4 is hydrogen and another is hydrogen, hydroxyl, hydroxyalkyl, etc., or both of R 3 and R 4 combine to form oxo group, R 5 is hydrogen or alkyl, Y is single bond, oxygen atom or a group of the formula: —N(R 7 )—, R 6 is optionally substituted hydrocarbon group or optionally substituted cyclic group, R 7 is alkyl or alkyloxycarbonylalkyl, provided that R 6 is not 4-amino-5-chloro-2-methoxyphenyl group when Y is single bond and one of the R 3 and R 4 is hydrogen and another is hydroxymethyl, or a pharmaceutically acceptable salt thereof.

  本发明涉及一种新型吡咯烷化合物，其具有对中枢大麻素（CB1）受体的强烈拮抗活性，其化学式为[I]：其中，R1和R2中的每一个是（A）可选取的取代芳基（或杂环芳基）基团，或者（B）两个基团结合形成式的基团：R3和R4中的一个是氢，另一个是氢、羟基、羟基烷基等，或者R3和R4结合形成氧代基团，R5是氢或烷基，Y是单键、氧原子或式的基团：—N(R7)—，R6是可选取的取代的碳氢基团或可选取的取代的环状基团，R7是烷基或烷氧羰基烷基，但当Y为单键且R3和R4中的一个为氢，另一个为羟甲基时，R6不是4-氨基-5-氯-2-甲氧基苯基团，或其药学上可接受的盐。
• Three-carbon annelations. Regiocontrolled reactivity of trimethylsilyl- and ethoxyethyl-protected cyanohydrins. Versatile homoenolate and acyl anion equivalents
  作者：Richard M. Jacobson、George P. Lahm、John W. Clader

  DOI：10.1021/jo01291a005

  日期：1980.2
• Stereoselective Syntheses of β,γ-Unsaturated Esters and γ-Lactones:  1-(Benzotriazol-1-yl)-3-(diphenylphosphoryl)-1-ethoxy-1-propene, a Protected CCH₂CO₂Et Synthon Equivalent
  作者：Alan R. Katritzky、Daming Feng、Hengyuan Lang

  DOI：10.1021/jo9701647

  日期：1997.6.13

  1-(Benzotriazol-1-yl)-3-(diphenylphosphoryl)-1-ethoxy-1-propene (3), prepared from N-(alpha-ethoxy-allyl)benzotriazole (1), underwent selective Horner reactions with aldehydes to give substituted dienes. Subsequent hydrolysis of these intermediates readily produced beta,gamma-unsaturated esters 2a-c in good yields. Similar reactions with ketones followed by hydrolysis of 10 produced, depending on the conditions, either the corresponding gamma,gamma-disubstituted beta,gamma-unsaturated esters 11a-d or gamma-lactones 9a-c and 13. A double lithiation process provided beta,gamma,gamma-trisubstituted beta,gamma-unsaturated esters 15, 18, and beta,gamma,gamma-trisubstituted gamma-lactone 14.
• Bunce, Richard A.; Drumright, Raymond E.; Taylor, Vicki L., Synthetic Communications, 1989, vol. 19, # 13-14, p. 2423 - 2430
  作者：Bunce, Richard A.、Drumright, Raymond E.、Taylor, Vicki L.

  DOI：——

  日期：——