(E)-(3-(but-3-yn-1-yloxy)prop-1-en-1-yl)benzene | 192431-31-5

• 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: (E)-(3-(but-3-yn-1-yloxy)prop-1-en-1-yl)benzene
• 英文别名: (E)-(3-(but-3-ynyloxy)prop-1-enyl)benzene；[(E)-3-but-3-ynoxyprop-1-enyl]benzene
• CAS: 192431-31-5
• 化学式: C₁₃H₁₄O
• 分子量: 186.254
• InChiKey: VYMSIGQJZDJASG-JXMROGBWSA-N

物化性质

• 沸点：
  292.9±33.0 °C(Predicted)
• 密度：
  0.998±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-(3-(but-3-yn-1-yloxy)prop-1-en-1-yl)benzene 在 disodium hydrogenphosphate 、 [RhCl2(p-cymene)]2 、 三(2-呋喃基)膦 、 2CF₃O₃S^(1-)*Cu⁽²⁺⁾*C₁₇H₂₈N₂O₂ 、 sodium carbonate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 33.5h， 生成
  参考文献：
  名称：

  ENANTIOSELECTIVE CROSS DEHYDROGENATIVE COUPLING REACTIONS AND COMPOUNDS SYNTHESIZED BY THE REACTIONS

  摘要：

  揭示了用于合成四氢吡喃化合物的对映选择性交叉脱氢偶联反应。根据所披露的方法可以合成新型四氢吡喃化合物，以及用于合成各种天然存在化合物的四氢吡喃前体化合物。对映选择性交叉脱氢偶联反应利用原位Lewis酸活化结合氧化形成氧杂环丙阳离子，提供了一种高效且选择性的偶联反应，用于合成四氢吡喃化合物。

  公开号：

  US20200181106A1
• 作为产物：
  描述：

  3-丁炔-1-氧化钠 、 Cinnamyl bromide 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 (E)-(3-(but-3-yn-1-yloxy)prop-1-en-1-yl)benzene
  参考文献：
  名称：

  Stereoselective Cyclizations and Rearrangements in Vinyl Radicals Promoted by Regioselective Sulfanyl Radical Addition to Enynes

  摘要：

  Regioselective radical addition of 4-cyanotoluenethiol (1a) to enynes 3-6 leads to vinyl radicals 7-10 that can undergo five- or six-membered cyclization onto styrene or terminal double bonds in competition with 5-exo cyclization onto the aryl ring, The latter affords spiro-cyclohexadienyl radical intermediates which can either be trapped by 2-cyanoisopropyl radicals or give 1,4-aryl migration products. Regioselective radical addition of phenethanethiol (1b) to enynes 3-6 gives radicals 11-14 which undergo five- or six-membered cyclization onto the alkene double bond; the stereoelectronically disfavored 6-exo cyclization can compete with intermolecular hydrogen abstraction and (to a small extent) with 1,5-hydrogen migration. The 5- and 6-(pi-exo)exo cyclization of vinyl radicals 7, 9, 11-13 is highly stereoselective and exclusively or predominately affords products deriving from the (Z)-isomers. Stereochemical evidence indicates that the six-membered endo-cyclization products 30 and 50 could derive from a direct 6-endo cyclization of (E)-radicals (E)-10 and (E)-14 rather than from a 5-exo cyclization/ring expansion process. Sulfanyl radical addition to enynes 3-5 is highly regioselective to the terminal triple bond. In contrast, reaction elf thiols 1a,b with enyne 6 leads to products deriving from sulfanyl radical addition to both the CC triple and double bond. This behavior is accounted for by assuming that sulfanyl radical addition to the alkyne triple bond is not reversible, while the addition to the alkene double bond is. Vinyl radical 10 affords product 33 by a rare 1,4-hydrogen migration/fragmentation process.

  DOI：

  10.1021/jo9701142

文献信息

• Gold-Catalysed Activation of Epoxides: Application in the Synthesis of Bicyclic Ketals
  作者：Rengarajan Balamurugan、Raveendra Babu Kothapalli、Ganesh Kumar Thota

  DOI：10.1002/ejoc.201001214

  日期：2011.3

  Gold-catalysed generation of diol equivalents from epoxides and their intramolecular reaction with C≡C bonds to generate bicyclic ketals is presented. This reaction essentially involves the formation of an acetonide, which subsequently cyclises on the alkyne intramolecularly under gold catalysis conditions. This method could be extended to make optically pure bicyclic ketals. Deuterium incorporation

  介绍了金催化从环氧化物生成二醇等价物及其与 C≡C 键的分子内反应生成双环缩酮。该反应主要涉及丙酮化物的形成，其随后在金催化条件下分子内在炔烃上环化。这种方法可以扩展到制造光学纯的双环缩酮。进行氘掺入实验以确定反应机理。
• Synthesis of Arylnaphthalene Lignan Scaffold by Gold-Catalyzed Intramolecular Sequential Electrophilic Addition and Benzannulation
  作者：Vanajakshi Gudla、Rengarajan Balamurugan

  DOI：10.1021/jo201918d

  日期：2011.12.16

  an arylnaphthalene lignan scaffold in high yields is presented. It involves a sequential intramolecular electrophilic attack of carbonyl on arylalkyne followed by benzannulation catalyzed by gold salt. AuCl3 in combination with AgSbF6 works better to effect this transformation. Selected products have been converted into arylnaphthalene lactone natural products such as justicidin E, taiwanin C, and

  提出了一种以高产率产生包含芳基萘木脂体骨架的化合物的分子内方法。它涉及羰基对芳基炔的连续分子内亲电攻击，然后由金盐催化苯环化。AuCl 3与AgSbF 6结合使用效果更好。某些产品已被转化为芳基萘内酯天然产品，例如司法正义素E，黄花青素C和逆转录调节素B。
• Broad-Spectrum Catalysts for the Ambient Temperature Anti-Markovnikov Hydration of Alkynes
  作者：Le Li、Mingshuo Zeng、Seth B. Herzon

  DOI：10.1002/anie.201404320

  日期：2014.7.21

  Anti‐Markovnikov alkyne hydration provides a valuable route to aldehydes. Half‐sandwich ruthenium complexes ligated by 5,5′‐bis(trifluoromethyl)‐2,2′‐bipyridine are remarkably active for this transformation. In the presence of 2 mol % metal, a wide range of functionalized aliphatic and aromatic alkynes are hydrated in high yield at ambient temperature.

  抗马尔科夫尼科夫炔烃水合为醛的合成提供了有价值的途径。由5,5'-双（三氟甲基）-2,2'-联吡啶连接的半三明治钌络合物对于该转化非常有效。在2mol％金属的存在下，在环境温度下高产率地将多种官能化的脂族和芳族炔烃水合。
• Enantioselective cross dehydrogenative coupling reactions and compounds synthesized by the reactions
  申请人：Northwestern University

  公开号：US11174238B2

  公开（公告）日：2021-11-16

  Disclosed are enantioselective cross dehydrogenative coupling reactions for synthesizing tetrahydropyran compounds. Novel tetrahydropyran compounds may be synthesized by the disclosed methods as well as tetrahydropyran precursor compounds for synthesizing various naturally occurring compounds. The enantioselective cross dehydrogenative coupling reactions utilize in situ Lewis Acid activation in combination with oxidative formation of an oxocarbenium ion to provide a highly efficient and selective coupling reaction for synthesizing tetrahydropyran compounds.

  公开了用于合成四氢吡喃化合物的对映体选择性交叉脱氢偶联反应。通过所公开的方法可以合成新型四氢吡喃化合物以及用于合成各种天然化合物的四氢吡喃前体化合物。对映选择性交叉脱氢偶联反应利用原位路易斯酸活化与氧化形成的氧羰基鎓离子相结合，为合成四氢吡喃化合物提供了一种高效和选择性的偶联反应。