1-(but-3-yn-1-yloxy)-3-methylbut-2-ene | 1403588-59-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(but-3-yn-1-yloxy)-3-methylbut-2-ene
• CAS: 1403588-59-9
• 化学式: C₉H₁₄O
• 分子量: 138.21
• InChiKey: AFJHEJFDRVYHIL-UHFFFAOYSA-N

物化性质

• 沸点：
  180.9±23.0 °C(Predicted)
• 密度：
  0.860±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.99
• 重原子数：
  10.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-(but-3-yn-1-yloxy)-3-methylbut-2-ene 在 1-hydroxytetraphenylcyclopentadienyl(tetraphenyl-2,4-cyclopentadien-1-one)-μ-hydrotetracarbonyldiruthenium(II) 、 Au(IPr)Cl 、 水 、 silver trifluoroacetate 作用下， 以 异丙醇 为溶剂， 反应 42.0h， 以80%的产率得到4-((3-methylbut-2-en-1-yl)oxy)butan-2-ol
  参考文献：
  名称：

  Regioselective Reductive Hydration of Alkynes To Form Branched or Linear Alcohols

  摘要：

  The regioselective reductive hydration of terminal alkynes using two complementary dual catalytic systems is described. Branched or linear alcohols are obtained in 75-96% yield with >= 25:1 regioselectivity from the same starting materials. The method is compatible with terminal, di-, and trisubstituted alkenes. This reductive hydration constitutes a strategic surrogate to alkene oxyfunctionalization and may be of utility in multistep settings.

  DOI：

  10.1021/ja307145e
• 作为产物：
  描述：

  异戊烯醇 在 三溴化磷 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醚 、 mineral oil 为溶剂， 反应 1.0h， 生成 1-(but-3-yn-1-yloxy)-3-methylbut-2-ene
  参考文献：
  名称：

  Gold-Catalyzed Formal Hexadehydro-Diels–Alder/Carboalkoxylation Reaction Cascades

  摘要：

  DOI：

  10.1021/acs.orglett.1c00581

文献信息

• Visible-Light-Mediated Chlorosulfonylative Cyclizations of 1,6-Enynes
  作者：Hong Hou、Hengxue Li、Yue Xu、Chuanqi Song、Chunling Wang、Yaocheng Shi、Ying Han、Chaoguo Yan、Shaoqun Zhu

  DOI：10.1002/adsc.201801157

  日期：2018.11.16

  Described herein is a visible‐light‐mediated atom‐transfer radical cyclization (ATRC) using 1,6‐enynes as substrates. The sulfonyl chlorides not only served as sulfonyl radical sources but also provided a chlorine atom to enable the formation of highly functionalized cyclic products. This visible‐light‐mediated photocatalytic method is a mild and practical strategy for synthesizing chloroalkyl‐substituted

  本文描述了一种以1,6-烯炔为底物的可见光介导的原子转移自由基环化（ATRC）。磺酰氯不仅用作磺酰基自由基源，而且提供了氯原子以能够形成高度官能化的环状产物。这种可见光介导的光催化方法是合成氯烷基取代的环状烯基砜的温和而实用的策略。
• Enantioselective Intramolecular C−H Insertion of Donor and Donor/Donor Carbenes by a Nondiazo Approach
  作者：Dong Zhu、Jun Ma、Kui Luo、Hongguang Fu、Li Zhang、Shifa Zhu

  DOI：10.1002/anie.201604211

  日期：2016.7.11

  The first enantioselective intramolecular C−H insertion and cyclopropanation reactions of donor‐ and donor/donor‐carbenes by a nondiazo approach are reported. The reactions were conducted in a one‐pot manner without slow addition and provided the desired dihydroindole, dihydrobenzofuran, tetrahydrofuran, and tetrahydropyrrole derivatives with up to 99 % ee and 100 % atom efficiency.

  报道了通过非重氮方法进行的供体和供体/供体碳烯的首次对映选择性分子内CH插入和环丙烷化反应。反应以单锅方式进行，无需缓慢添加，并提供所需的二氢吲哚，二氢苯并呋喃，四氢呋喃和四氢吡咯衍生物，其ee最高可达99％，原子效率为100％。
• Atom Transfer Radical Addition to Alkynes and Enynes: A Versatile Gold/Photoredox Approach to Thio-Functionalized Vinylsulfones
  作者：Haoyu Li、Zengrui Cheng、Chen-Ho Tung、Zhenghu Xu

  DOI：10.1021/acscatal.8b02194

  日期：2018.9.7

  visible-light photoredox catalysis and gold catalysis has been developed, affording diverse trifluoromethylthio- and difluoromethylthio-functionalized vinylsulfones with high stereoselectivity in good yields. Thiosulfonylation reaction of enyne can also be realized for constructing functionalized carbo- and heterocycles through a radical cascade cyclization process. These reactions proceed through a gold-assisted

  已经开发了通过可见光光氧化还原催化和金催化相结合的炔烃的有效分子间原子转移加成反应，从而以良好的产率提供了具有高立体选择性的各种三氟甲硫基和二氟甲硫基官能化的乙烯基砜。还可以通过自由基级联环化过程实现烯炔的硫磺酰化反应，以构建官能化的碳环和杂环。这些反应通过金辅助的磺酰基自由基加成途径进行。
• Mechanism‐Based Approach to Reagent Selection for Oxidative Carbon−Hydrogen Bond Cleavage Reactions
  作者：Jenna L. Miller、Lin Zhou、Peng Liu、Paul E. Floreancig

  DOI：10.1002/chem.202103078

  日期：2022.1.3

  Selecting the optimal reagent for an oxidative C−H cleavage reaction requires mechanistic understanding of these processes. This manuscript describes an experimental approach to identify the role of substrate oxidation potential, cation stability, and steric factors on reaction rates and yields with common oxidants. The results are explained through computational transition state energetic and geometric

  为氧化性 C-H 裂解反应选择最佳试剂需要对这些过程的机械理解。这份手稿描述了一种实验方法，用于确定底物氧化电位、阳离子稳定性和空间因素对常见氧化剂的反应速率和产率的作用。结果通过计算过渡态能量和几何分析来解释。
• Synthesis of Cyclopropyl-Substituted Furans by Brønsted Acid Promoted Cascade Reactions
  作者：J. Stephen Clark、Filippo Romiti、Kirsten F. Hogg、Malai Haniti S. A. Hamid、Sven C. Richter、Alistair Boyer、Joanna C. Redman、Louis J. Farrugia

  DOI：10.1002/anie.201500625

  日期：2015.5.4

  Chloroacetic acid promotes an efficient and diastereoselective intramolecular cascade reaction of electron‐deficient ynenones to deliver products featuring a 2,3,5‐trisubstituted furan bearing a fused cyclopropyl substituent at the 5‐position. Synthetically relevant polycyclic building blocks featuring rings of various sizes and heteroatoms have been synthesized in high yield using this mild acid‐catalyzed

  氯乙酸可促进电子不足的炔烃的高效非对映选择性分子内级联反应，以提供具有在5位带有稠合环丙基取代基的2,3,5-三取代呋喃的产物。使用这种温和的酸催化反应，可以高收率合成具有各种尺寸和杂原子的环的合成相关多环结构单元。