1-cyclopentylpentan-1-one | 6636-80-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-cyclopentylpentan-1-one
• 英文别名: 1-Cyclopentyl-pentan-1-on
• CAS: 6636-80-2
• 化学式: C₁₀H₁₈O
• mdl: MFCD03658911
• 分子量: 154.252
• InChiKey: RBXGUJOEERWYQB-UHFFFAOYSA-N

物化性质

• 沸点：
  104-106 °C(Press: 25 Torr)
• 密度：
  0.893 g/cm3(Temp: 23 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  11
• 可旋转键数：
  4
• 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：

  三甲基氯硅烷 、 1-cyclopentylpentan-1-one 在 三乙胺 、 lithium diisopropyl amide 作用下， 生成 (1-Cyclopentylidene-pentyloxy)-trimethyl-silane 、 ((Z)-1-Cyclopentyl-pent-1-enyloxy)-trimethyl-silane 、 ((E)-1-Cyclopentyl-pent-1-enyloxy)-trimethyl-silane
  参考文献：
  名称：

  Generation, alkylation, and silylation of directed enolates formed by reaction of ketenes and organolithium reagents

  摘要：

  DOI：

  10.1021/jo00212a019
• 作为产物：
  描述：

  环戊基甲醛 在 乙醚 、 铬酸 作用下， 生成 1-cyclopentylpentan-1-one
  参考文献：
  名称：

  Vavon; Guedon, Bulletin de la Societe Chimique de France, 1930, vol. <4> 47, p. 901,905

  摘要：

  DOI：

文献信息

• Continuous Flow Synthesis of Ketones from Carbon Dioxide and Organolithium or Grignard Reagents
  作者：Jie Wu、Xiaoqing Yang、Zhi He、Xianwen Mao、T. Alan Hatton、Timothy F. Jamison

  DOI：10.1002/anie.201405014

  日期：2014.8.4

  describe an efficient continuous flow synthesis of ketones from CO2 and organolithium or Grignard reagents that exhibits significant advantages over conventional batch conditions in suppressing undesired symmetric ketone and tertiary alcohol byproducts. We observed an unprecedented solvent‐dependence of the organolithium reactivity, the key factor in governing selectivity during the flow process. A facile

  我们描述了由CO 2和有机锂或格氏试剂的有效连续流动合成酮，在抑制不希望的对称酮和叔醇副产物方面，与常规间歇条件相比，它显示出显着优势。我们观察到有机锂反应性的前所未有的溶剂依赖性，这是控制流动过程中选择性的关键因素。还建立了一种通过在线生成有机金属试剂以模块化方式制备酮的简便，可伸缩的三步一流工艺。
• <i>N</i>-Arylsulfonylamidines; Part 2.¹A New Synthesis of Ketones from<i>N</i>′-Tosylamidines and Organolithium Compounds
  作者：Francesca Clerici、Maria Luisa Gelmi、Luisa Maria Rossi

  DOI：10.1055/s-1987-28159

  日期：——

  Tertiary N′-arylsulfonylamidines readily react with organolithium compounds under simple conditions to afford carbonyl compounds.

  第三级N′-芳基磺酰胺在简单条件下能与有机锂化合物迅速反应，生成羰基化合物。
• PROCESS FOR PREPARATION OF NORBORNENE DERIVATIVES
  申请人：JX Nippon Oil & Energy Corporation

  公开号：EP2444386A1

  公开（公告）日：2012-04-25

  A method for producing a norbornene derivative, comprising: a first step of forming a Mannich base by reacting a carbonyl compound and an amine compound with each other in an acidic solvent, to thereby obtain a reaction liquid comprising the Mannich base in the acidic solvent, the acidic solvent comprising a formaldehyde derivative and 0.01 mol/L or more of an acid represented by the formula: HX (In the formula, X represents F or the like), the carbonyl compound being represented by any of the following general formulae (1) to (3): [in formulae (1) to (3), R1, R2, R3, R4, R5, and R6 each independently represent a hydrogen atom or the like, and n represents an integer of any of 0 to 4], the amine compound being represented by the following general formula (4): [in the formula (4), R7S each independently represent a linear chain saturated hydrocarbon group having 1 to 20 carbon atoms or the like, and X- represents F- or the like], the Mannich base being represented by any of the following general formulae (5) to (7): [R1, R2, R3, R4, R5, R6, and n in the formulae (5) to (7) have the same meanings as those of R1, R2, R3, R4, R5, R6, and n in the formulae (1) to (3), and R7 and X- in the formulae (5) to (7) have the same meanings as those of R7 and X- in the formula (4)] and a second step of reacting the Mannich base and a diene compound with each other by adding an organic solvent, a base in an amount of 1.0 to 20.0 equivalents to the acid, and the diene compound to the reaction liquid, and then heating the reaction liquid, to thereby form a norbornene derivative, the diene compound being represented by the following general formula (8): [in the formula (8), R8 represents a hydrogen atom or the like], the norbornene derivative being represented by any of the following general formulae (9) to (11): [R1, R2, R3, R4, R5, R6, and n in the formulae (9) to (11) have the same meanings as those of R1, R2, R3, R4, R5, R6, and n in the formulae (1) to (3), and R8 in the formulae (9) to (11) has the same meaning as that of R8 in the formula (8)].

  一种制备去氢莰烯衍生物的方法，包括以下步骤：第一步，在酸性溶剂中使羰基化合物和胺基化合物反应，形成曼尼希碱，从而在酸性溶剂中获得包含曼尼希碱的反应液，所述酸性溶剂包括甲醛衍生物和代表为HX的酸，其中HX中的X代表F或类似物，所述羰基化合物由以下通式（1）至（3）中的任一通式表示：[在通式（1）至（3）中，R1、R2、R3、R4、R5和R6各自独立地代表氢原子或类似物，n代表0至4中的任一整数]，所述胺基化合物由以下通式（4）表示：[在通式（4）中，R7S各自独立地代表具有1至20个碳原子或类似物的线性链饱和碳氢基团，X-代表F-或类似物]，所述曼尼希碱由以下通式（5）至（7）中的任一通式表示：[在通式（5）至（7）中，R1、R2、R3、R4、R5、R6和n的含义与通式（1）至（3）中的R1、R2、R3、R4、R5、R6和n的含义相同，通式（5）至（7）中的R7和X-的含义与通式（4）中的R7和X-的含义相同]；第二步，通过向反应液中加入有机溶剂、相当于酸的1.0至20.0当量的碱和二烯化合物，然后加热反应液，使曼尼希碱与二烯化合物发生反应，从而形成去氢莰烯衍生物，所述二烯化合物由以下通式（8）表示：[在通式（8）中，R8代表氢原子或类似物]，所述去氢莰烯衍生物由以下通式（9）至（11）中的任一通式表示：[在通式（9）至（11）中，R1、R2、R3、R4、R5、R6和n的含义与通式（1）至（3）中的R1、R2、R3、R4、R5、R6和n的含义相同，通式（9）至（11）中的R8的含义与通式（8）中的R8的含义相同]。
• THE REACTION OF TRIALKYLBORANES WITH THE (α-LITHIO DERIVATIVES OF BIS(PHENYLTHIO)METHANE AND OF 1,1-BIS(PHENYLTHIO)PENTANE. A CONVENIENT METHOD FOR THE PREPARATION OF ALDEHYDES AND KETONES
  作者：Shoji Yamamoto、Manzo Shiono、Teruaki Mukaiyama

  DOI：10.1246/cl.1973.961

  日期：1973.9.5

  It was found that various aldehydes and ketones were readily prepared in good yields by the reactions of α-lithio derivatives of thioacetals with trialkylboranes.

  发现通过硫缩醛的 α-锂硫衍生物与三烷基硼烷的反应，可以很容易地以良好的收率制备各种醛和酮。
• Reaction of Organoboranes with Lithium Aldimines. A New Procedure for the Synthesis of Unsymmetrical Ketones
  作者：Yoshinori Yamamoto、Kaoru Kondo、Ichiro Moritani

  DOI：10.1246/bcsj.48.3682

  日期：1975.12

  via the reaction of dialkylchloroboranes with lithium aldimines followed by treatment with (i) thioglycolic acid and (ii) H2O2–NaOH. The reaction permits the introduction of both primary and secondary alkyl groups into R and R′ substituents of ketones (RR′C=O), and can even be extended to the accommodation of a functional group. The reaction of B-n-hexyl-9-borabicyclo[3.3.1]-nonane with lithium aldimine

  通过二烷基氯硼烷与醛亚胺锂反应，然后用 (i) 巯基乙酸和 (ii) H2O2-NaOH 处理，以良好的收率获得不对称酮。该反应允许将伯烷基和仲烷基引入酮的 R 和 R' 取代基 (RR'C=O)，甚至可以扩展到容纳官能团。Bn-hexyl-9-borabicyclo[3.3.1]-nonane 与衍生自正丁基锂的醛亚胺锂的反应，在用 H2O2-NaOH 处理后也会得到不对称的酮，5-十一酮。