2-propylcyclopentane-1,3-dione | 824-26-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-propylcyclopentane-1,3-dione
• 英文别名: 2-Propyl-cyclopentan-1,3-dion；2-Propyl-cyclopentandion-(1,3)；2-Propyl-1,3-cyclopentanedione
• CAS: 824-26-0
• 化学式: C₈H₁₂O₂
• 分子量: 140.182
• InChiKey: FSCAEMWIILOKLC-UHFFFAOYSA-N

物化性质

• 熔点：
  175 °C
• 沸点：
  248.5±23.0 °C(Predicted)
• 密度：
  1.032±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  2-propylcyclopentane-1,3-dione 在 mercury(II) sulfate sodium hydroxide 、 硫酸 、 水 作用下， 以 甲醇 、 水 为溶剂， 生成 2-propyl-2-(2-oxopropyl)cyclopentane-1,3-dione
  参考文献：
  名称：

  Conversion of 2-Alkyl-2-(2-oxopropyl)cyclopentane-1,3-diones into 2,3,5- and 2,3,4-Trisubstituted Cyclopent-2-enones by Intramolecular Aldolizations to 2,3-Diacylcyclopropanolates Followed by Remarkable Skeletal Rearrangements¹

  摘要：

  2-Alkyl-2-(prop-2-ynyl)cyclopentane-1,3-diones 2, conveniently prepared from 2-alkylcyclopentane-1,3-diones 1 and prop-2-ynyl bromide, afford the triketones 3 by Hg2+-catalyzed hydration of the acetylenic triple bond. Treatment of these triketones with aqueous sodium hydroxide gives rise to the 2,3,5-trisubstituted cyclopent-2-enones 5, which are accompanied by the isomeric 2,3,4-trisubstituted cyclopent-2-enones 7 as byproducts. The formation of these isomers can be avoided, when the 2,2-disubstituted cyclopentane-1,3-diones 2 are first converted by ring cleavage into the 5-alkyl-4-oxooct-7-ynaic acids 4 and then by subsequent hydration into the 5-alkyl-4,7-dioxoalkanoic acids 6. An intramolecular aldolization of the latter forms exclusively the cyclopentenones 5. A mechanism explaining the simultaneous formation of 5 and 7 from 3 is based on the formation of the 2,3-diacylcyclopropanolates 11 and 16 by intramolecular aldolization and subsequent ring opening to the 2-acetylcyclohexane-1,4-diones 13 and 18. A further ring opening to the 4,7-dioxoalkanoates 15 and 20 followed by intramolecular aldol condensation then gives rise to the isomeric trisubstituted cyclopent-2-enones 5 and 7.

  DOI：

  10.1021/jo960189q
• 作为产物：
  描述：

  4-环戊烯-1,3-二酮 在 palladium on activated charcoal 氢气 、 乙酸酐 、 zinc(II) chloride 作用下， 以 乙醇 为溶剂， 生成 2-propylcyclopentane-1,3-dione
  参考文献：
  名称：

  2-取代的环戊烷-1,3-二酮的新合成。

  摘要：

  2-甲基、2-丙基和2-苯乙基环戊烯-1, 3-二酮（III）是通过相应的2-(α-乙氧烷基烯基)环戊烯-1, 3-二酮（II）的催化氢化制备的，后者是通过环戊烯-1, 3-二酮（I）与邻酸的乙酯的缩合反应得到的。

  DOI：

  10.1248/cpb.15.670

文献信息

• Synthesis of 13-alkyl-gon-4-ones
  申请人：Smith; Herchel

  公开号：US03959322A1

  公开（公告）日：1976-05-25

  The preparation of 13-methylgon-4-enes and novel 13-polycarbonalkylgon-4-enes by a new total synthesis is described. 13-Alkylgon-4-enes having progestational, anabolic and androgenic activities are prepared by forming a tetracylic gonane structure unsaturated in the 1,3,5(10),9(11) and 14-positions, selectively reducing in the B- and C-rings, and converting the aromatic A-ring compounds so-produced to gon-4-enes by Birch reduction and hydrolysis.

  描述了通过新的全合成方法制备13-甲基孕-4-烯和新型13-聚碳烷基孕-4-烯。通过形成在1,3,5(10),9(11)和14-位置不饱和的四环孕烷结构，选择性地在B和C环中还原，并将所产生的芳香A环化合物转化为孕-4-烯，制备具有孕激素、合成激素和雄激素活性的13-烷基孕-4-烯。
• Synthesis of gon-4-enes
  申请人：Smith; Herchel

  公开号：US04002746A1

  公开（公告）日：1977-01-11

  1. A therapeutic composition having progestational activity comprising as active ingredient a 17-aliphatic carboxylic acid ester of 17.alpha.-ethynyl-18-methyl-19-nortestosterone and a pharmaceutical carrier for said compound.

  一种具有孕激素活性的治疗组合物，其活性成分为17-脂肪族羧酸酯的17α-乙炔基-18-甲基-19-去甲睾酮，以及用于该化合物的药用载体。
• Enamine derivatives
  申请人：——

  公开号：US20020037909A1

  公开（公告）日：2002-03-28

  Enamine derivatives of formula (1) are described: 1 wherein R 1 is a group Ar 1 L 2 Ar 2 Alk- in which Ar 1 is an aromatic or heteroaromatic group, L 2 is a covalent bond or a linker atom or group, Ar 2 is an arylene or heteroarylene group and Alk is a chain —CH 2 —CH(R)—, —CH═C(R)— or 2 in which R is a carboxylic acid or a derivative or biostere thereof; R 2 is a hydrogen atom or a C 1-6 alkyl group; Cy is a cycloaliphatic or heterocycloaliphatic ring in which X is a N atom or a C(R w ) group; R x is a oxo, thioxo, or imino group; R w and R z is each a hydrogen atom or optional substituent; provided that Cy is not a cyclobutenedione group; and the salts, solvates, hydrates and N-oxides thereof. The compounds are able to inhibit the binding of integrins to their ligands and are of use in the prophylaxis and treatment of immune or inflammatory disorders, or disorders involving the inappropriate growth or migration of cells.

  描述了公式（1）的Enamine衍生物：其中R1是Ar1L2Ar2Alk-中的一个基团，其中Ar1是芳香族或杂环芳基，L2是共价键或连接原子或基团，Ar2是芳基或杂环芳基，Alk是链—CH2—CH（R）—，—CH═C（R）—或其中R是羧酸或其衍生物或生物类似物；R2是氢原子或C1-6烷基基团；Cy是环脂环或杂环脂环，其中X是N原子或C（Rw）基团；Rx是氧化、硫代氧化或亚胺基团；Rw和Rz分别是氢原子或可选取代基；前提是Cy不是环丁二酮基团；以及它们的盐、溶剂合物、水合物和N-氧化物。这些化合物能够抑制整合素与其配体的结合，并可用于预防和治疗免疫或炎症性疾病，或涉及细胞异常生长或迁移的疾病。
• Enantio- and Diastereoselective Synthesis of Functionalized Carbocycles by Cu-Catalyzed Borylative Cyclization of Alkynes with Ketones
  作者：Joseph M. Zanghi、Shuang Liu、Simon J. Meek

  DOI：10.1021/acs.orglett.9b01769

  日期：2019.7.5

  and diastereoselective tandem hydroboration/borylative cyclization of alkynes with ketones for the synthesis of carbocycles is reported. The reaction proceeds via desymmetrization and generates four contiguous stereocenters, including an all-carbon quaternary center. The method provides rapid access to [6,5]- and [5,5]-bicycles and cyclopentane products. Catalyst-controlled diastereoselectivity by selection

  据报道，炔烃与酮的单锅铜催化对映和非对映选择性串联硼氢化/硼化环化反应可用于合成碳环。反应通过去对称化进行，并产生四个连续的立体中心，包括全碳四元中心。该方法提供了对[6,5]-和[5,5]-自行车和环戊烷产物的快速访问。注意到通过选择双膦配体的催化剂控制的非对映选择性。通过提供有价值的烯基和烯丙基有机硼的位点和化学选择性转化证明了产品的实用性。
• Copper‐Nitrene‐Catalyzed Desymmetric Oxaziridination/1,2‐Alkyl Rearrangement of 1,3‐Diketones toward Bicyclic Lactams
  作者：Xue Han、Li‐Xin Shan、Jin‐Xin Zhu、Chang‐Sheng Zhang、Xiao‐Ming Zhang、Fu‐Min Zhang、Hong Wang、Yong‐Qiang Tu、Ming Yang、Wen‐Shuo Zhang

  DOI：10.1002/anie.202107909

  日期：2021.10.11

  oxaziridination reaction of cyclic diketones with alkyl azides and the subsequent rearrangement of the resulting highly active intermediate, which produces a synthetically challenging chiral bicyclic lactam containing a quaternary carbon center. This procedure not only enriches the copper-nitrene-catalyzed asymmetric reactions, but also provides an alternative strategy to address the inherent challenges of catalytic

  尽管铜-氮烯作为多种转化中的通用活性物质已被广泛研究，但涉及铜-氮烯的不对称反应仅限于烯烃的氮丙啶化反应。在此，我们报告了新型铜-氮烯催化的环状二酮与烷基叠氮化物的去对称 oxaziridination 反应以及所得高活性中间体的后续重排，该反应产生了具有合成挑战性的含有季碳中心的手性双环内酰胺。该过程不仅丰富了铜-氮烯催化的不对称反应，而且还提供了一种替代策略来解决催化不对称施密特反应的固有挑战。