4-cyclopentylbut-2-ynal | 6053-44-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-cyclopentylbut-2-ynal
• 英文别名: 4-cyclopentyl-2-butynal；1-Formyl-3-cyclopentyl-prop-1-in
• CAS: 6053-44-7
• 化学式: C₉H₁₂O
• 分子量: 136.194
• InChiKey: JXYDCISXWUGBLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  4-cyclopentylbut-2-ynal 在 碘 、 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 5-(cyclopentylmethyl)-4-iodo-1-phenyl-1H-pyrazole
  参考文献：
  名称：

  Synthesis of Pyrazoles via Electrophilic Cyclization

  摘要：

  Electrophilic cyclizations of alpha,beta-alkynic hydrazones by molecular iodine were investigated for the synthesis of 4-iodopyrazoles. alpha,beta-Alkynic hydrazones were readily prepared by the reactions of hydrazines with propargyl aldehydes and ketones. When treated with molecular iodine in the presence of sodium bicarbonate, alpha,beta-alkynic hydrazones underwent electrophilic cyclization to afford 4-iodopyrazoles in good to high yields. Iodocyclization was general for a wide range of alpha,beta-alkynic hydrazones and tolerated the presence of aliphatic, aromatic, heteroaromatic, and ferrocenyl moieties with electron-withdrawing and electron-donating substituents.

  DOI：

  10.1021/jo201119e
• 作为产物：
  描述：

  3-环戊基-1-丙炔 、 N,N-二甲基甲酰胺 在 正丁基锂 、 potassium dihydrogenphosphate 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 4-cyclopentylbut-2-ynal
  参考文献：
  名称：

  Synthesis of Pyrazoles via Electrophilic Cyclization

  摘要：

  Electrophilic cyclizations of alpha,beta-alkynic hydrazones by molecular iodine were investigated for the synthesis of 4-iodopyrazoles. alpha,beta-Alkynic hydrazones were readily prepared by the reactions of hydrazines with propargyl aldehydes and ketones. When treated with molecular iodine in the presence of sodium bicarbonate, alpha,beta-alkynic hydrazones underwent electrophilic cyclization to afford 4-iodopyrazoles in good to high yields. Iodocyclization was general for a wide range of alpha,beta-alkynic hydrazones and tolerated the presence of aliphatic, aromatic, heteroaromatic, and ferrocenyl moieties with electron-withdrawing and electron-donating substituents.

  DOI：

  10.1021/jo201119e

文献信息

• A novel synthesis of 1,2,4-oxadiazoles and isoxazoles
  作者：Arif Kivrak、Metin Zora

  DOI：10.1016/j.tet.2013.12.043

  日期：2014.1

  A novel synthesis of 1,2,4-oxadiazoles and isoxazoles is described by utilizing the reactions between amidoximes and α,β-alkynic aldehydes and/or ketones. Conjugate addition products, obtained from amidoximes and α,β-alkynic aldehydes and/or ketones, afford 1,2,4-oxadiazoles and isoxazoles when treated with bases and acids, respectively. 1,2,4-Oxadiazoles can also be synthesized directly from amidoximes

  通过利用a肟和α，β-炔醛和/或酮之间的反应，描述了1,2,4-恶二唑和异恶唑的新型合成方法。从a胺肟和α，β-炔醛和/或酮获得的共轭加成产物在分别用碱和酸处理时分别得到1,2,4-恶二唑和异恶唑。1,2,4-氧杂二唑也可以在碱性条件下一锅法直接由a胺肟和α，β-炔醛合成。该反应对于各种起始化合物是通用的，并且可以耐受芳基，杂芳基和烷基的存在。
• Catalytic enantioselective allylboration of propargylic aldehydes
  作者：Urmibhusan Bhakta、Erin Sullivan、Dennis G. Hall

  DOI：10.1016/j.tet.2013.11.095

  日期：2014.1

  Homoallylic propargylic alcohols are important building blocks in natural product synthesis. This moiety can be transformed into various other structures by performing other known transformations, which can in turn lead to the synthesis of biologically useful compounds. Herein, a methodology based on Lewis acid assisted Brønsted acid catalysed allylboration of propargylic aldehydes is described. A

  均烯丙基炔丙醇是天然产物合成中的重要组成部分。该部分可以通过进行其他已知的转化而转化成各种其他结构，这又可以导致生物学上有用的化合物的合成。在本文中，描述了基于路易斯酸辅助布朗斯台德酸催化的炔丙基醛的烯丙基硼化的方法。已经探索了详细的优化研究，然后彻底检查了底物范围。