己-2-炔-1-醛 | 27593-24-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 己-2-炔-1-醛
• 英文名称: hex-2-ynal
• 英文别名: 2-hexyne-1-al；2-hexynal；Hydrohexalin
• CAS: 27593-24-4
• 化学式: C₆H₈O
• 分子量: 96.1289
• InChiKey: IUPHFACLDYMBNL-UHFFFAOYSA-N

物化性质

• 熔点：
  -61°C (estimate)
• 沸点：
  169.66°C (estimate)
• 密度：
  0.8948 (estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  己-2-炔-1-醛 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以40%的产率得到1-戊炔
  参考文献：
  名称：

  Jones, Ewart R. H.; Macrides, Theodore A.; Thaller, Viktor, Journal of Chemical Research, Miniprint, 1981, # 6, p. 2017 - 2030

  摘要：

  DOI：
• 作为产物：
  描述：

  2-已炔 在 甲酸 作用下， 反应 0.25h， 以60%的产率得到己-2-炔-1-醛
  参考文献：
  名称：

  Jones, Ewart R. H.; Macrides, Theodore A.; Thaller, Viktor, Journal of Chemical Research, Miniprint, 1981, # 6, p. 2017 - 2030

  摘要：

  DOI：

文献信息

• Rhodium-Catalyzed 1,1-Hydroacylation of Thioacyl Carbenes with Alkynyl Aldehydes and Subsequent Cyclization
  作者：Bingnan Zhou、Qiuyue Wu、Ziyang Dong、Jiaxi Xu、Zhanhui Yang

  DOI：10.1021/acs.orglett.9b01003

  日期：2019.5.17

  A rhodium-catalyzed 1,1-hydroacylation of thioacyl carbenes with alkynyl and alkenyl aldehydes and subsequent 6-endo-trig/dig cyclization are realized, giving structurally diverse 4H-thiopyran-4-ones and 2,3-dihydro-4H-thiopyran-4-ones in moderate to good yields. The oxidative addition of Rh(I) to aldehydes is proposed to be the turnover-limiting step. Manipulations of estrones demonstrate the applications

  实现了铑的羰基羰基与炔基和烯基醛催化的1,1-氢羰基化反应，随后进行了6-内-trig / dig环化反应，得到了结构上不同的4 H - thiopyran -4-ones和2,3-dihydro-4 H -thiopyran-4-ones，产量中等至良好。提出将Rh（I）氧化成醛是限制营业额的步骤。雌酮的操作证明了我们正式的（3 + 3）转环剂在天然产物的结构修饰中的应用。
• Highly regioselective dipolar cycloadditions of nitrile oxides with α,β-acetylenic aldehydes
  作者：Longqiang Jiang、Tao Gao、Zhi Li、Shaofa Sun、Claudia Kim、Changfeng Huang、Haibing Guo、Jian Wang、Yalan Xing

  DOI：10.1016/j.tetlet.2016.01.019

  日期：2016.2

  1,2-Oxazol derivatives 3 were prepared by a highly regioselective 1,3-dipolar cycloaddition of nitrile oxides and α,β-acetylenicaldehydes 1 in good yields. Reactive nitrile oxides were generated in situ from stable chloro-oxime reagents 2 and triethyl amine. The cycloaddition reaction showed broad substrate scope and good functional group compatibility.

  -1,2-恶唑衍生物3由腈氧化物和α的高度选择性1,3-偶极环加成制备，β-acetylenicaldehydes 1以良好的收率。由稳定的氯代肟试剂2和三乙胺原位生成反应性一氧化氮。环加成反应显示出较宽的底物范围和良好的官能团相容性。
• Zinc-Catalyzed [4+3] Cycloaddition with Concomitant Furan Annulation: Formation of Cyclohepta[<i>b</i>]Furans
  作者：Bo Song、Lian-Hua Li、Xian-Rong Song、Yi-Feng Qiu、Mei-Jin Zhong、Ping-Xin Zhou、Yong-Min Liang

  DOI：10.1002/chem.201402513

  日期：2014.5.12

  A convenient zinc‐promoted [4+3] cycloaddition of a carbonyl ene–yne with simple dienes was first achieved. This reaction provided an efficient strategy to prepare various cyclohepta[b]furan rings by cascade cycloadditions. Additionally, a multicomponent reaction of dione, alkynal, and diene was also reported, which exhibited a novel strategy for selective creations of CO bonds and CC bonds.

  首先实现了一种简单的锌促进的羰基烯-炔的锌促进的[4 + 3]环加成反应。该反应提供了通过级联环加成反应制备各种环庚[ b ]呋喃环的有效策略。此外，二酮，炔醛，和二烯的多组分反应也有报道，其显示了用于使C选择性创作的新策略 O键和C  C键。
• Cycloisomerization of acetylenic oximes and hydrazones under gold catalysis: Synthesis and cytotoxic evaluation of isoxazoles and pyrazoles
  作者：J C JEYAVEERAN、CHANDRASEKAR PRAVEEN、Y ARUN、A A M PRINCE、P T PERUMAL

  DOI：10.1007/s12039-015-0993-9

  日期：2016.1

  The synthesis of substituted isoxazoles and pyrazoles through a general cycloisomerization methodology has been reported. The capability of gold(III) chloride to promote cycloisomerization of both α, β-acetylenic oximes and α, β-acetylenic hydrazones is the centrepiece of the strategy. A range of acetylenic precursors were investigated to afford 28 examples of the products with good to excellent chemical yields. Selected compounds were screened for their cytotoxic potential towards COLO320 cancer cell lines. The IC50 values of the tested compounds were in the micromolar range, with the best compound, 5-(6-Methoxy-naphthalen-2-yl)-3-phenyl-isoxazole (3h) displaying an IC50 of 38.9 μM. For this compound, the crystal structure in complex with Aurora-A kinase was obtained which revealed details of its binding mode within the active site with a free energy of binding -9.54 kcal/mol.

  通过一种通用的环异构化方法，已经报道了取代异恶唑和吡唑的合成。金(III)氯化物促进α,β-炔基肟和α,β-炔基脒的环异构化的能力是该策略的核心。研究了一系列炔基前体，以良好的至优秀的化学收率得到了28个产物实例。选定的化合物对COLO320癌细胞系的细胞毒性潜力进行了筛选。测试化合物的IC50值在微摩尔范围内，其中最佳化合物5-(6-甲氧基萘-2-基)-3-苯基异恶唑(3h)的IC50值为38.9 μM。对于该化合物，获得了与Aurora-A激酶复合的晶体结构，揭示了其在活性位点内的结合模式，结合自由能为-9.54 kcal/mol。
• Gold-Catalyzed Deacylative Cycloisomerization Reactions of 3-Acylindole/ynes: A New Approach for Carbazole Synthesis
  作者：Lu Wang、Guijie Li、Yuanhong Liu

  DOI：10.1021/ol2012154

  日期：2011.8.5

  The synthesis of functionalized carbazoles through gold-catalyzed deacylative cycloisomerization of 3-acylindole/ynes is described. A mechanistic proposal for these transformations involving a novel carbonyl group facilitated heterolytic fragmentation upon the loss of an acylium ion intermediate is presented. The eliminated acylium ion species could be trapped by the organogold intermediate to afford

  描述了通过金催化的3-丙烯腈/炔的脱酰基环异构化来合成官能化咔唑的方法。提出了一种针对这些转化的机制建议，其中涉及一种新的羰基基团，可在失去酰基离子中间体后促进杂化断裂。消除的胞嘧啶离子种类可以被有机金中间体捕获，得到酰基咔唑。