4-pentyl-1,3-cyclohexanedione | 63649-30-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-pentyl-1,3-cyclohexanedione
• 英文别名: 4-pentylcyclohexane-1,3-dione；Pentyl-4-cyclohexandion-1,3；4-Pentyl-cyclohexandion-(1,3)；4-Pentyl-cyclohexan-1,3-dion
• CAS: 63649-30-9
• 化学式: C₁₁H₁₈O₂
• 分子量: 182.263
• InChiKey: WMFBEKBUSVGTGL-UHFFFAOYSA-N

物化性质

• 熔点：
  62-64 °C
• 沸点：
  298.9±23.0 °C(Predicted)
• 密度：
  0.977±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-pentyl-1,3-cyclohexanedione 在 盐酸羟胺 、 碳酸氢钠 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  Synthesis of 3-Acetoxyacetanilide Derivatives by means of Semmler–Wolff-type Aromatization Reaction of Cyclohexane-1,3-dione Monooximes

  摘要：

  描述了一种由取代的环己烷-1,3-二酮合成3-乙酰氧基苯胺衍生物的新方法。该合成过程包括环己烷-1,3-二酮单肟 2 的区域选择性形成及其在非常简单的反应条件下的 Semmler-Wolff 型芳构化。

  DOI：

  10.1246/cl.2008.1066
• 作为产物：
  描述：

  4-戊基间苯二酚 在 sodium hydroxide 、 镍 作用下， 125.0 ℃ 、18.63 MPa 条件下， 生成 4-pentyl-1,3-cyclohexanedione
  参考文献：
  名称：

  Structure of Cannabinol. IV. Synthesis of Two Additional Isomers Containing a Resorcinol Residue¹

  摘要：

  DOI：

  10.1021/ja01865a084

文献信息

• Synthesis and polymerization of methacroylacetone
  作者：Ph. Teyssié、G. Smets

  DOI：10.1002/macp.1958.020260122

  日期：1958.1

  The synthesis of a polymerizable β‐diketone, methacroylacetone, by the usual acylation of an ester by a ketone in the presence of sodium methoxide, is described. However, the reaction with acrylic and methacrylic ester yielded important amounts of secondary products, especially substituted cyclohexanediones; a reaction scheme is proposed, which proceeds through an intermediate MICHAEL addition. The monomeric diketone was polymerized and a high polymer (D. P. 235), was obtained which forms metal chelate complexes analogous to that of the monomer.

  摘要 描述了在甲醇钠存在下，通过酮对酯进行通常的酰化反应，合成可聚合的 β-二酮，即甲基丙基丙酮。然而，与丙烯酸酯和甲基丙烯酸酯的反应产生了大量的次级产物，特别是取代的环己烷二酮。对单体二酮进行聚合，得到了一种高聚物（D. P. 235），它能形成与单体类似的金属螯合物。
• [EN] NOVEL HERBICIDES<br/>[FR] NOUVEAUX HERBICIDES
  申请人：SYNGENTA LTD

  公开号：WO2010046194A1

  公开（公告）日：2010-04-29

  Cyclohexanedione compounds, which are suitable for use as herbicides.

  环己烷二酮化合物，适用于作为除草剂。
• NOVEL HERBICIDES
  申请人：Mathews Christopher John

  公开号：US20120035053A1

  公开（公告）日：2012-02-09

  Cyclohexanedione compounds, which are suitable for use as herbicides.

  环己二酮化合物，适用于作为除草剂。
• Pd/C-Catalyzed Carbonylative Amidation for the Synthesis of 2-Carboxamidocyclohexane-1,3-diones
  作者：Sheetal、Arvind Singh Chauhan、Ajay Kumar Sharma、Navneet Sharma、Kousik Giri、Pralay Das

  DOI：10.1021/acs.orglett.3c02808

  日期：2023.11.24

  first-ever heterogeneous Pd/C-catalyzed single-step tandem approach for the synthesis of 2-carboxamidocyclohexane-1,3-diones via direct carbonylative C–H amidation of cyclohexane-1,3-diones is reported. The reaction progressed under base-, oxidant-, and ligand-free conditions employing oxalic acid as a CO surrogate and sodium azide as a nitrogen precursor in a double-layer vial system.

  在此，报道了有史以来第一个非均相 Pd/C 催化的单步串联方法，通过环己烷-1,3-二酮的直接羰基化 C-H 酰胺化合成 2-甲酰胺基环己烷-1,3-二酮。该反应在双层小瓶系统中，在无碱、无氧化剂和无配体的条件下进行，使用草酸作为CO替代物，叠氮化钠作为氮前体。
• Revisiting [3 + 3] Route to 1,3-Cyclohexanedione Frameworks:  Hidden Aspect of Thermodynamically Controlled Enolates
  作者：Teruhiko Ishikawa、Ryuichiro Kadoya、Masaki Arai、Haruka Takahashi、Yumi Kaisi、Tomohiro Mizuta、Kazusa Yoshikai、Seiki Saito

  DOI：10.1021/jo010325d

  日期：2001.11.1

  We have revisited the traditional consecutive Michael-Claisen [3 + 3] process (MC-[3 + 3]) promising the synthesis of a cyclohexane-1,3-dione derivatives from nonactivated simple ketones and enoates and evaluated its potential in modern organic synthesis. Twenty to thirty examples were demonstrated to be effective. The reactions exhibited remarkable regioselectivity with the Michael addition proceeding through nucleophilic attack by the more hindered site of the ketones without exception. The subsequent Claisen condensation resulted in the formation of carbon-carbon bonds between less hindered site of the ketones and acyl carbon of the enoates. The MC-[3 + 3] process described is useful for the synthesis of Taxol A-ring synthons in multigram quantities and for the synthesis of other six-membered carbocyclic compounds. A number of control experiments have been conducted to provide strong support for the mechanism of this MC-[3 + 3].