3-methyl-1-phenyl-pent-4-yn-2-ol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-methyl-1-phenyl-pent-4-yn-2-ol
• 英文别名: 3-Methyl-1-phenylpent-4-yn-2-ol；3-methyl-1-phenylpent-4-yn-2-ol
• 化学式: C₁₂H₁₄O
• 分子量: 174.243
• InChiKey: YZLVZJIDLXCTSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-methyl-1-phenyl-pent-4-yn-2-ol 在 Jones reagent 、 溶剂黄146 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 反应 2.0h， 生成 3,4,6-trimethyl-1-phenyl-1H-quinolizin-2(9aH)-one
  参考文献：
  名称：

  Sustainable and selective synthesis of 3,4-dihydroquinolizin-2-one and quinolizin-2-one derivatives via the reactions of penta-3,4-dien-2-ones

  摘要：

  本文中开发了一种新型绿色合成方法，通过在常温下用水乙醇将三烯-2-酮与吡啶、喹啉或异喹啉进行串联反应合成3,4-二氢喹嗪-2-酮衍生物。值得注意的是，这些反应涉及简单的沉淀和过滤操作，且溶剂可以轻易回收。此外，当反应在更高温度下进行较长时间时，原位生成的3,4-二氢喹嗪-2-酮可以通过空气中的分子氧进行脱氢，生成有效率较高的喹嗪-2-酮。

  DOI：

  10.1039/c3gc42093k
• 作为产物：
  描述：

  氧化苯乙烯 、 3-溴-1-丁炔 在 palladium diacetate tin(ll) chloride 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 14.0h， 以71%的产率得到3-methyl-1-phenyl-pent-4-yn-2-ol
  参考文献：
  名称：

  Highly efficient water promoted allylation and propargylation of arylepoxides via rearrangement-carbonyl addition

  摘要：

  A simple and highly efficient one-pot procedure for allylation and propargylation of arylepoxides has been developed. A combination of SnCl2 and catalytic Pd(0) or Pd(II) promotes the reaction of organic halides and epoxides in DMSO with controlled water addition, leading to the regioselective formation of the corresponding homoallyl and homopropargyl alcohols in good yields. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.10.005

文献信息

• Allylation and propargylation of aldehydes mediated by <i>in situ</i> generated zinc from the redox couple of Al and ZnCl₂ in 2N HCl
  作者：Bibhas Mondal、Utpal Adhikari、Partha Pratim Hajra、Ujjal Kanti Roy

  DOI：10.1039/d1nj00978h

  日期：——

  A simple one pot allylation and propargylation of aldehydes mediated by zinc(0), which is in situ generated from the redox couple of Al and ZnCl₂ in 2N HCl, is demonstrated to afford the corresponding homoallyl and homopropargyl alcohols with excellent yields.

  通过锌（0）介导的醛的简单一锅烯丙基化和丙炔基化，在2N HCl中由Al和ZnCl₂的氧化还原偶产生锌（0），可获得相应的同烯丙基和同丙炔基醇，收率极高。
• One-pot cascade reactions of 1-arylpenta-3,4-dien-2-ones leading to 2-arylphenols and dibenzopyroanones
  作者：Yan He、Xinying Zhang、Xuesen Fan

  DOI：10.1039/c4cc06204c

  日期：——

  of 1-arylpenta-3,4-dien-2-ones with activated ketones allowed for an efficient and sustainable synthesis of 2-arylphenols. Moreover, this reaction was also found to be compatible and combinable with Pd-catalyzed C-H activation and carbonylation of the in situ formed 2-aryl phenols, thus resulting in a highly convenient and atom-economic synthesis of dibenzopyranones.

  1-芳基戊基3,4-二烯-2-酮与活化酮的一锅级联反应可实现2-芳基苯酚的有效和可持续合成。此外，还发现该反应与Pd催化的CH活化和原位形成的2-芳基酚的羰基化相容并且可组合，从而导致二苯并吡喃酮的高度方便和原子经济的合成。
• Stereoselectivity in (Z)-Vinylmetal Additions to the Dictyostatin C1-C9 β-Silyloxy Aldehyde
  作者：Andrea Ambrosi、Luca Pignataro、Chiara Zanato、Cesare Gennari

  DOI：10.1002/ejoc.201101201

  日期：2012.1

  vinyllithium additions. The configuration of the newly created C9 stereocenter was assigned through Rychnovsky's acetonide 13C NMR method. The diastereoselectivity in this particular type of (Z)-vinylmetal addition reaction appears to be controlled by a subtle balance between the intrinsic stereochemical preference of the β-silyloxy aldehyde (1,3-anti-selective) and that of the chiral lithium (Z)-vinylzincates

  (Z) -乙烯基碘化物 6a - d 以高收率合成，具有良好的非对映选择性和对映选择性，使用 Marshall-Tamaru，Pd 催化的烯基锌反应作为关键步骤。通过乙烯基锂和乙烯基锌酸锂路线将 6a-d 添加到 dictyostatin C1-C9 β-甲硅烷氧基醛 5。与相应的乙烯基锂添加相比，乙烯基锌酸锂的添加总是以更高的产率进行并且产生更少的副产物。新创建的 C9 立体中心的配置是通过 Rychnovsky 的 acetonide 13C NMR 方法分配的。这种特定类型的 (Z) - 乙烯基金属加成反应中的非对映选择性似乎受 β-甲硅烷氧基醛（1,3-反选择性）和手性锂（Z ) 乙烯基锌酸盐。
• Tuning the reactivity of organotin(IV) by LiOH: allylation and propargylation of epoxides via redox transmetalation
  作者：Moloy Banerjee、Ujjal Kanti Roy、Pradipta Sinha、Sujit Roy

  DOI：10.1016/j.jorganchem.2004.12.008

  日期：2005.3

  In presence of catalytic Pd(0) or Pt(II), a reagent combination of SnCl2-LiOH promotes the reaction of organic halides and epoxides in dichloromethane leading to the regioselective formation of corresponding homoallyl and homopropargyl alcohols in good yields. This 2-carbon extension strategy adds to the repertoire of Barbier reactions via metal salts and reinforces views on the enhanced reactivity of organotin having -OH pendant. (c) 2004 Elsevier B.V. All rights reserved.
• Sustainable and selective synthesis of 3,4-dihydroquinolizin-2-one and quinolizin-2-one derivatives via the reactions of penta-3,4-dien-2-ones
  作者：Xuesen Fan、Yan He、Xinying Zhang、Jianji Wang

  DOI：10.1039/c3gc42093k

  日期：——

  In this paper, a novel and green methodology for the synthesis of 3,4-dihydroquinolizin-2-one derivatives via the tandem reactions of penta-3,4-dien-2-ones with pyridine, quinoline, or isoquinoline at rt in aqueous ethanol was developed. Notably, the reactions involved a convenient work-up of simple precipitation and filtration, and the solvent could be easily recycled. In addition, when the reactions were carried out at higher temperature over a prolonged reaction period, the in situ formed 3,4-dihydroquinolizin-2-ones could be dehydrogenated by molecular oxygen from air to afford quinolizin-2-ones with good efficiency.

  本文中开发了一种新型绿色合成方法，通过在常温下用水乙醇将三烯-2-酮与吡啶、喹啉或异喹啉进行串联反应合成3,4-二氢喹嗪-2-酮衍生物。值得注意的是，这些反应涉及简单的沉淀和过滤操作，且溶剂可以轻易回收。此外，当反应在更高温度下进行较长时间时，原位生成的3,4-二氢喹嗪-2-酮可以通过空气中的分子氧进行脱氢，生成有效率较高的喹嗪-2-酮。