5-((Tert-butyldimethylsilyl)oxy)-2-methylpent-3-yn-2-yl methyl carbonate | 1225232-79-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: 5-((Tert-butyldimethylsilyl)oxy)-2-methylpent-3-yn-2-yl methyl carbonate
• 英文别名: [5-[tert-butyl(dimethyl)silyl]oxy-2-methylpent-3-yn-2-yl] methyl carbonate
• CAS: 1225232-79-0
• 化学式: C₁₄H₂₆O₄Si
• 分子量: 286.444
• InChiKey: OUYNVKOJJUIBNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.57
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-((Tert-butyldimethylsilyl)oxy)-2-methylpent-3-yn-2-yl methyl carbonate 在 2-pentafluorophenyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate 、 四丁基氟化铵 、 碳酸氢钠 、 戴斯-马丁氧化剂 、 N-氟代双苯磺酰胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 13.0h， 生成 ethyl 2-fluoro-4-methylpenta-2,3-dienoate
  参考文献：
  名称：

  α-Fluoroallenoate Synthesis via N-Heterocyclic Carbene-Catalyzed Fluorination Reaction of Alkynals

  摘要：

  The first catalytic alpha-fluoroallenoate synthesis is described. With a suitable combination of N-heterocyclic carbene precatalyst, base, and fluorine reagent, the reaction proceeded smoothly to yield a wide range of alpha-fluoroallenoates with excellent chemoselectivity. These substituted alpha-fluorinated allenoates have been synthesized for the first time, and they are versatile synthetic intermediates toward other useful fluorine-containing building blocks.

  DOI：

  10.1021/acs.orglett.5b03615
• 作为产物：
  描述：

  叔丁基二甲基(2-丙炔氧基)硅烷 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.5h， 生成 5-((Tert-butyldimethylsilyl)oxy)-2-methylpent-3-yn-2-yl methyl carbonate
  参考文献：
  名称：

  α-Fluoroallenoate Synthesis via N-Heterocyclic Carbene-Catalyzed Fluorination Reaction of Alkynals

  摘要：

  The first catalytic alpha-fluoroallenoate synthesis is described. With a suitable combination of N-heterocyclic carbene precatalyst, base, and fluorine reagent, the reaction proceeded smoothly to yield a wide range of alpha-fluoroallenoates with excellent chemoselectivity. These substituted alpha-fluorinated allenoates have been synthesized for the first time, and they are versatile synthetic intermediates toward other useful fluorine-containing building blocks.

  DOI：

  10.1021/acs.orglett.5b03615

文献信息

• Catalytic Enantioselective Synthesis of β-Allenyl Boronic Esters by Conjunctive Cross-Coupling with Propargylic Carbonates
  作者：Mark D. Aparece、Weipeng Hu、James P. Morken

  DOI：10.1021/acscatal.9b04453

  日期：2019.12.6

  Enantioselective conjunctive cross-coupling with propargylic carbonates affords β-boryl allenes as the reaction product. The reaction is found to proceed through the intermediacy of dimethoxyboronate complexes that are generated in situ by a strain-induced ligand exchange reaction.

  与炔丙基碳酸酯的对映选择性联合交叉偶联提供了作为反应产物的β-硼基烯丙基。发现该反应通过由应变诱导的配体交换反应在原位产生的二甲氧基硼酸酯络合物的中间进行。
• Palladium-Catalyzed Cyclization Reactions of 2,3-Allenyl Amines with Propargylic Carbonates
  作者：Juntao Ye、Suhua Li、Shengming Ma

  DOI：10.1021/ol3007293

  日期：2012.5.4

  A highly efficient and atom-economic route to synthesize 5-(1,3,4-alkatrien-2-yl)oxazolidin-2-ones via palladium-catalyzed cyclization reactions of 2,3-allenyl amines with propargylic carbonates was reported. The CO2 generated in situ from propargylic carbonates is incorporated into the oxazolidin-2-one unit with high efficiency, affording the products in 70–92% yields.

  据报道，通过钯催化的2,3-烯基胺与碳酸炔丙基酯的环化反应，可以合成5-（1,3,4-烷基三烯-2-基）恶唑烷-2-酮的高效且经济的路线。由炔丙基碳酸酯原位产生的CO 2被高效地引入到恶唑烷-2-一单元中，从而使产物的收率达到70-92％。
• Palladium-catalyzed synthesis of 1,3,4-alkatrien-2-yldihydrofurans from 2,3-allenylacetylacetates and propargylic carbonates and their application to synthesize polysubstituted dihydrofurylcyclopentenones
  作者：Wei Shu、Shengming Ma

  DOI：10.1016/j.tet.2010.02.030

  日期：2010.4

  and regioselective palladium(0)-catalyzed coupling–cyclization reaction of 2-(2′,3′-allenyl)acetylacetates with propargylic carbonates was reported. The reaction proceeded smoothly under neutral conditions, affording the O-attacked five-membered products with a 1,3,4-trienyl substituent exclusively in good to excellent yields. The products can be efficiently applied to the synthesis of polysubstituted

  报道了一种通过高化学和区域选择性钯（0）催化2-（2'，3'-烯基）乙酰乙酸与炔丙基碳酸酯的偶合-环化反应生产1,3,4-烷基三烯-2-基二氢呋喃的有效途径。反应在中性条件下顺利进行，得到具有1,3,4-三烯基取代基的O-攻击的五元产物，收率很高，而且收率极好。该产品可在环境条件下通过催化Pauson-Khand反应有效地用于合成多取代的2-（二氢呋喃基）环戊烯酮衍生物。
• Palladium-catalysed construction of butafulvenes
  作者：Xin Huang、Bing-Zhi Chen、Pengbin Li、Ding-Wei Ji、Jinxian Liu、Hao Zheng、Sa-Na Yang、Yan-Cheng Hu、Boshun Wan、Xiang-Ping Hu、Chunling Fu、Yankai Huang、Jian Zheng、Qing-An Chen、Shengming Ma

  DOI：10.1038/s41557-022-01017-9

  日期：2022.10

  of the intrinsic high strain energy and anti-aromaticity, the preparation of butafulvene compounds has been a fundamental issue for the development of butafulvene chemistry. Here an efficient palladium-catalysed coupling protocol involving propargylic compounds has been developed, providing a solid and versatile strategy for the rapid assembly of symmetric butafulvene derivatives. Based on mechanistic

  丁富烯是苯的结构异构体，包含带有两个环外共轭亚甲基单元的环丁烯骨架。由于其固有的高应变能和抗芳香性，丁富烯化合物的制备一直是丁富烯化学发展的一个基本问题。在这里，已经开发出一种涉及炔丙基化合物的高效钯催化偶联方案，为对称丁富烯衍生物的快速组装提供了可靠且通用的策略。基于机理研究，已经证实了两种互补的机理，都涉及钯催化。随着机理的揭示，也实现了非对称丁富烯的合成。该策略的优点包括对广泛的炔丙基分子的耐受性，温和的反应条件，简单的催化系统和易于扩展。该产品作为环丁烯衍生物的平台分子的合成潜力也已得到证实。