(5S)-5-异丙基-2-甲基环己酮 | 160168-89-8

• 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: (5S)-5-异丙基-2-甲基环己酮
• 英文名称: (5S)-2-methyl-5-(methylethyl)cyclohexan-1-one
• 英文别名: (1S)-carvomenthone；(5S)-carvomenthone；carvomenthone；(-)-Tetrahydrocarvon；(-)-Carvomenthon；(5S)-2-methyl-5-propan-2-ylcyclohexan-1-one
• CAS: 160168-89-8
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: GCRTVIUGJCJVDD-GKAPJAKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (5S)-5-异丙基-2-甲基环己酮 在 tris-(dibenzylideneacetone)dipalladium(0) 、 三乙胺 、 (S)-4-叔丁基-2-[2-(二苯基膦基)苯基]-2-噁唑啉 、 四丁基二氟三苯硅酸铵 、 sodium iodide 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 9.0h， 生成 (2S,5S)-2-methyl-5-(methylethyl)-2-prop-2-enylcyclohexan-1-one
  参考文献：
  名称：

  First total syntheses of bicyclic marine sesquiterpenoids drechslerines A and B

  摘要：

  The first total syntheses of the bicyclic sesquiterpenoids drechslerines A (1) and B (2), which were isolated from the algicolous fungus Drechslera dematioidea in the marine red alga Liagora viscida, has been accomplished starting from (S)-carvone (13) via three palladium-catalyzed reactions, namely, diastereoselective allylation, conjugate reduction, and carbon monoxide insertion, as the key reactions. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.04.007
• 作为产物：
  描述：

  (1R,2S,4S)-4-isopropyl-1-methylcyclohexane-1,2-diol 在 硫酸 作用下， 生成 (5S)-5-异丙基-2-甲基环己酮
  参考文献：
  名称：

  Piatkowski,K. et al., Bulletin de l'Academie Polonaise des Sciences, Serie des Sciences Chimiques, 1975, vol. 23, p. 503 - 511

  摘要：

  DOI：

文献信息

• A convenient preparation of 3-isopropyl-1-methylcyclopentylmethanol and 1-isopropyl-3-methylcyclopentylmethanol via Favorskii rearrangement
  作者：Martino Ambrosini、Nikla Baricordi、Simonetta Benetti、Carmela De Risi、Gian P. Pollini、Vinicio Zanirato

  DOI：10.1016/j.tetasy.2009.08.016

  日期：2009.9

  The Favorskii rearrangement of suitable α-chloro derivatives of commercially available (+)- and (−)-carvone, and (−)-menthone served efficiently to prepare the title compounds featuring delicious fruity, floral olfactory notes.

  市售（+）-和（-）-香芹酮和（-）-薄荷酮的合适α-氯衍生物的Favorskii重排可有效地制备具有美味果味，花香味的标题化合物。
• Stereoselective synthesis of (6R)- and (6S)-diosphenol and Ψ-diosphenol
  作者：David F Schneider、Murray S Viljoen

  DOI：10.1016/s0040-4020(02)00492-1

  日期：2002.6

  Methods are discussed for the stereoselective synthesis of the (R)-and (S)-enantiomers of the diosphenols (5)–(8) by utilizing the commercially available stereoisomers (9), (12), (23) and (25) of carvone and limonene, respectively, as chiral starting materials.

  讨论了利用市售的立体异构体（9），（12），（23）和（25）对二酚（5）-（8）的（R）和（S）-对映异构体进行立体选择性合成的方法。香芹酮和柠檬烯分别作为手性原料。
• Oxidoreduction between Cycloalkanols and Cycloalkanones in the Cultured Cells of<i>Nicotiana tabacum</i>. Simulation of the Time-courses in the Oxidation of (+)-Borneol and the Reduction of (−)-Carvomenthone
  作者：Takayuki Suga、Shunsuke Izumi、Toshifumi Hirata、Hiroki Hamada

  DOI：10.1246/cl.1987.425

  日期：1987.2.5

  The time-courses in the oxidation of (+)-borneol and the reduction of (−)-carvomenthone in the cultured cells of Nicotiana tabacum were simulated on the basis of the permeability of 5- to 7-membered cycloalkanols and their corresponding cycloalkanones into the cultured cells and the 13C NMR chemical shift of the carbonyl carbon of (+)-camphor which is the oxidation product of (+)-borneol and (−)-carvomenthone which is a substrate for the reduction, respectively.

  根据 5 至 7 元环烷醇及其相应环烷酮对培养细胞的渗透性，以及作为 (+)-borneol 氧化产物的 (+)-camphor 和作为还原底物的 (-)-carvomenthone 的羰基碳的 13C NMR 化学位移，模拟了 (+)-borneol 和 (-)-carvomenthone 在烟草培养细胞中氧化和还原的时间历程、分别为
• Platinum Nanoparticles Stabilized by Glycerodendrimers: Synthesis and Application to the Hydrogenation of α,β‐Unsaturated Ketones under Mild Conditions
  作者：Bérengère Menot、Lionel Salmon、Sandrine Bouquillon

  DOI：10.1002/ejic.201500530

  日期：2015.9

  Air-stable platinum nanoparticles stabilized by glycerodendrimers were prepared in water and analyzed by TEM. These platinum nanoparticles showed good catalytic activity for the reduction of α,β-unsaturated ketones to saturated ketones at room temperature in water or in water/THF (1:1) under H2 (101.3 kPa). The catalytic species was recovered and recycled several times.

  在水中制备由甘油树枝状聚合物稳定的空气稳定铂纳米颗粒并通过 TEM 进行分析。这些铂纳米颗粒在室温下在水中或在水/THF (1:1) 中，在 H2 (101.3 kPa) 下显示出良好的催化活性，可将 α,β-不饱和酮还原为饱和酮。催化物质被回收和循环多次。
• Cyclopropyl Participation in the Carane System
  作者：Paul J. Kropp

  DOI：10.1021/ja00973a029

  日期：1966.11