1-环戊基-2-丙炔-1-酮 | 70639-95-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-环戊基-2-丙炔-1-酮
• 英文名称: cyclopentyl ethynyl ketone
• 英文别名: 1-Cyclopentyl-prop-2-in-1-on；1-Cyclopentylprop-2-yn-1-one
• CAS: 70639-95-1
• 化学式: C₈H₁₀O
• 分子量: 122.167
• InChiKey: RFHXDLFNFGHXPY-UHFFFAOYSA-N

物化性质

• 沸点：
  192℃
• 密度：
  1.015
• 闪点：
  67℃

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  1-环戊基-2-丙炔-1-酮 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 甲烷磺酸 、 palladium 10% on activated carbon 、 氢气 、 碳酸氢钠 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 水 、 异丙醇 、 甲苯 为溶剂， -85.0~45.0 ℃ 、446.08 kPa 条件下， 反应 11.01h， 生成 (R)-6-cyclopentyl-6-(2-(2,6-diethylpyridin-4-yl)ethyl)-dihydro-2H-pyran-2,4(3H)-dione
  参考文献：
  名称：

  Synthesis of Filibuvir. Part I. Diastereoselective Preparation of a β-Hydroxy Alkynyl Oxazolidinone and Conversion to a 6,6-Disubstituted 2H-Pyranone

  摘要：

  This is the first in a series of three papers describing the identification and development of a commercial synthesis of filibuvir (1). This contribution describes development of an Evans aldol reaction to control the tertiary alcohol stereocenter, a challenging variant of that strategy in that both reacting partners were nonstandard (acetate etiolate and ketone electrophile). A sequence consisting of Sonogashira coupling, acylation and hydrogenation delivered acetate 24, and Dieckmann cyclization provided beta-keto lactone 2.

  DOI：

  10.1021/op4002356
• 作为产物：
  描述：

  环戊基甲酰氯 在 Sodium tetraborate decahydrate 、 乙酰氯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 1-环戊基-2-丙炔-1-酮
  参考文献：
  名称：

  α-炔酮热环化成2-环戊烯† ‡

  摘要：

  α-炔烃的热环化成2-环戊烯酮

  DOI：

  10.1002/hlca.19790620324

文献信息

• Asymmetric Catalytic Double Michael Additions for the Synthesis of Spirooxindoles
  作者：Tengfei Kang、Peng Zhao、Jian Yang、Lili Lin、Xiaoming Feng、Xiaohua Liu

  DOI：10.1002/chem.201800043

  日期：2018.3.12

  Asymmetric cascade double Michael additions to construct 2′‐substituted 3,3′‐spirooxindoles by using a chiral guanidine organocatalyst has been developed. A series of spirooxindole derivatives containing dihydrofuran or pyrrolidine subunits were obtained with good to excellent diastereo‐ and enantioselectivities. The method showed great tolerance of a number of aromatic and aliphatic alkynones. The

  已经开发出通过使用手性胍有机催化剂来构建2'-取代的3,3'-spirooxindoles的不对称级联双Michael加成反应。得到了一系列含有二氢呋喃或吡咯烷亚基的螺氧杂吲哚衍生物，具有良好的非对映选择性和对映选择性。该方法显示出对许多芳族和脂族炔酮的高度耐受性。该策略首次提供了（-）-salacin的不对称合成方法。
• CuX Dual Catalysis: Construction of Oxazolo[2,3-<i>b</i>][1,3]oxazines via a Tandem CuAAC/Ring Cleavage/[4+2+3] Annulation Reaction
  作者：Xiai Luo、Zhongtao Yang、Jia Zheng、Gang Liang、Hui Luo、Weiguang Yang

  DOI：10.1021/acs.orglett.2c02705

  日期：2022.10.14

  catalyst strategy that promotes the tandem transformations of fused oxazolo[2,3-b][1,3]oxazines has been developed. Copper catalyzed terminal ynones, sulfonyl azides, and nitriles for the CuAAC/ring cleavage/[4+2] annulation reaction, while the halogen catalyzed ring cleavage and [2+3] annulation of oxiranes to form the final fused products. This study provides a four-component, one-pot strategy for synthesizing

  CuX 是一种简单的双催化剂策略，可促进稠合恶唑并 [2,3- b ][1,3] 恶嗪的串联转化。铜催化末端炔酮、磺酰叠氮化物和腈用于CuAAC/环裂解/[4+2]环化反应，而卤素催化环裂解和环氧乙烷的[2+3]环化形成最终的稠合产物。本研究为从简单成分合成复杂稠合杂环提供了一种四组分一锅法策略，并扩展了 CuAAC 在有机合成中的应用。
• Radical Coupling Initiated by Organophosphine Addition to Ynoates
  作者：Jing Cao、Antonia Seitz、José A. Forni、Anastasios Polyzos、David W. Lupton

  DOI：10.1002/anie.202303869

  日期：2023.7.17

  Combining established two electron nucleophilic catalysis of organophosphines with photoredox organocatalysis has allowed the discovery of a mechanistically unusual Giese coupling reaction. In addition to addressing a limitation in traditional photoredox coupling with electron-poor alkynes these studies demonstrate the viability of reaction designs that merge traditional nucleophilic phosphines organocatalysis

  将已建立的有机膦的两个电子亲核催化与光氧化还原有机催化相结合，发现了机械上不寻常的吉斯偶联反应。除了解决传统光氧化还原与缺电子炔烃偶联的局限性之外，这些研究还证明了将传统亲核膦有机催化和光氧化还原事件结合起来的反应设计的可行性。
• [4.2.0]bicyclooctane derivatives, process for their preparation and pharmaceutical compositions containing same
  申请人：SYNTEX (U.S.A.) INC.

  公开号：EP0196617A1

  公开（公告）日：1986-10-08

  Compounds useful in treating cardiovascular disorders' such as thrombosis, hypertension, and atherosclerosis are compounds depicted in formulas (1), (2), and (3): wherein: n is 2 or 3; R1 is CH20H, CHO, CO2R or CO2H; R2 is hydrogen or methyl; and R3 is linear or branched alkyl having 5-10 carbon atoms, optionally substituted with lower alkyl, lower alkoxy, trifluoromethyl, or halogen, in which a is 0, 1 or 2; b is 3-7; m is 0, 1 or 2; and or in which R4 is independently hydrogen or lower alkyl having 1-6 carbon atoms; and the pharmaceutically acceptable, non-toxic salts and esters thereof.

  用于治疗心血管疾病如血栓形成、高血压和动脉粥样硬化的化合物是式 (1)、(2) 和 (3) 所示的化合物：其中：n 是 2 或 3；R1 是 CH20H、CHO、CO2R 或 CO2H；R2 是氢或甲基；R3 是具有 5-10 个碳原子的直链或支链烷基，可任选被低级烷基、低级烷氧基、三氟甲基或卤素取代，其中 a 是 0、1 或 2；b 是 3-7；m 是 0、1 或 2；或 R4 独立地是氢或具有 1-6 个碳原子的低级烷基；以及它们的药学上可接受的无毒盐和酯。
• Novel substituted (4.2.0)Bicyclooctane derivatives with valuable therapeutic properties
  申请人：SYNTEX (U.S.A.) INC.

  公开号：EP0257609A2

  公开（公告）日：1988-03-02

  Compounds useful in treating cardiovascular disorders such as thrombosis, hypertension and atherosclerosis , in inhibiting gastric acid secretion and in preventing and treating peptic and intestinal ulcers, are depicted in formulas (1), (2) and (3) : wherein: A is -C≡C-, trans -HC = CH-, -CH2CH2-or -CH=CHCH2-; X is lower alkoxy, hydroxy, or (2,2,2)-trifluoroethoxy; Y is hydrogen, exo-(lower alkyl) or endo-(lower alkyl); n is an integer of 2-4; R1 is -CH2OH, -CHO, -CO2R or -COzH, and the olefin formed by the R1(CHz) nCH = moiety is either (E) or (Z); R2 is hydrogen or methyl, or optionally -CH = CH2 when A is -CH = CHCHr; and R3 is linear or branched alkyl, alkenyl or alkynyl having 5-10 carbon atoms, , -(CH2)m -phenyl or CH2O-phenyl; in which each phenyl may be optionally substituted with lower alkyl, lower alkoxy, trifluoromethyl, or halogen; in which: a is an integer of 0, 1 or 2; b is an integer of 3-7; m is an integer of 0, 1 or 2; and R is wherein X is or in which each R4 is independently hydrogen or lower alkyl having 1-6 carbon atoms, and the pharmaceutically acceptable, non-toxic salts and esters thereof.

  可用于治疗心血管疾病（如血栓形成、高血压和动脉粥样硬化）、抑制胃酸分泌以及预防和治疗消化性溃疡和肠溃疡的化合物如式(1)、(2)和(3)所示： 其中 A 是-C≡C-、反式-HC = CH-、- -或-CH=CH -； X 是低级烷氧基、羟基或 (2,2,2)-三氟乙氧基； Y 是氢、外-（低级烷基）或内-（低级烷基）； n 是 2-4 的整数； R1 是- OH、-CHO、-CO2R 或-COzH，R1(CHz) nCH = 分子形成的烯烃是 (E) 或 (Z)； R2 是氢或甲基，或当 A 是-CH = CHCHr 时，任选为-CH = CH2；以及 R3 是具有 5-10 个碳原子的直链或支链烷基、烯基或炔基、 ，-( )m-苯基或 O-苯基； 其中每个苯基可任选被低级烷基、低级烷氧基、三氟甲基或卤素取代； 其中：a 是 0、1 或 2 的整数； b 是 3-7 的整数 m 是 0、1 或 2 的整数；以及 R 是 其中 X 是 或 其中每个 R4 独立地为氢或具有 1-6 个碳原子的低级烷基，及其药学上可接受的无毒盐和酯。