4-((1-methoxycarbonyloxy-cycloheptyl)ethynyl)-benzoic acid methyl ester | 952527-74-1

• 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: 4-((1-methoxycarbonyloxy-cycloheptyl)ethynyl)-benzoic acid methyl ester
• 英文别名: methyl [1-(phenylethynyl)cycloheptyl] carbonate；Methyl [1-(2-phenylethynyl)cycloheptyl] carbonate
• CAS: 952527-74-1
• 化学式: C₁₇H₂₀O₃
• 分子量: 272.344
• InChiKey: GQLIMUWKTQMUDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-((1-methoxycarbonyloxy-cycloheptyl)ethynyl)-benzoic acid methyl ester 在 四(三苯基膦)钯 zinc trifluoromethanesulfonate 作用下， 以 四氢呋喃 、 水 、 苯 为溶剂， 反应 48.0h， 生成 3-cyclohept-1-enyl-1-(4-nitro-phenyl)-4-phenyl-pyrrole-2,5-dione
  参考文献：
  名称：

  Efficient Synthesis of Maleimides and Carbazoles via Zn(OTf)₂-Catalyzed Tandem Annulations of Isonitriles and Allenic Esters

  摘要：

  Lewis acid Zn(OTf)(2)-catalyzed tandem annulations of isonitriles and allenic esters which lead to efficient and flexible syntheses of a range of biologically significant maleimides and carbazoles and related compounds are reported. A mechanistic rationale is proposed to account for the observed reactivity.

  DOI：

  10.1021/ol7018086
• 作为产物：
  描述：

  氯甲酸甲酯 、 苯乙炔 、 环庚酮 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.5h， 以95%的产率得到4-((1-methoxycarbonyloxy-cycloheptyl)ethynyl)-benzoic acid methyl ester
  参考文献：
  名称：

  Efficient Synthesis of Maleimides and Carbazoles via Zn(OTf)₂-Catalyzed Tandem Annulations of Isonitriles and Allenic Esters

  摘要：

  Lewis acid Zn(OTf)(2)-catalyzed tandem annulations of isonitriles and allenic esters which lead to efficient and flexible syntheses of a range of biologically significant maleimides and carbazoles and related compounds are reported. A mechanistic rationale is proposed to account for the observed reactivity.

  DOI：

  10.1021/ol7018086

文献信息

• Manganese(I)‐Catalyzed C−H Activation/Diels–Alder/retro‐Diels–Alder Domino Alkyne Annulation featuring Transformable Pyridines
  作者：Cuiju Zhu、Rositha Kuniyil、Lutz Ackermann

  DOI：10.1002/anie.201900495

  日期：2019.4.8

  Complexity‐increasing Domino reactions comprising C−H allenylation, a Diels–Alder reaction, and a retro‐Diels–Alder reaction were realized by a versatile catalyst derived from earth‐abundant, non‐toxic manganese. The C−H activation/Diels–Alder/retro‐Diels–Alder alkyne annulation sequence provided step‐economical access to valuable indolone alkaloid derivatives through a facile organometallic C−H activation

  通过衍生自地球上丰富的无毒锰的多功能催化剂，实现了包括CH烯基化，Diels-Alder反应和Diels-Alder逆反应在内的增加Domino的反应。C-H活化/ Diels-Alder / retro-Diels-Alder炔烃环化序列通过简便的有机金属CH-H活化歧管和可转化的吡啶为您提供了经济实用的有价值的吲哚酮生物碱衍生物的经济途径。
• Mn‐Catalyzed Dehydrocyanative Transannulation of Heteroarenes and Propargyl Carbonates through C−H Activation: Beyond the Permanent Directing Effects of Pyridines/Pyrimidines
  作者：Guangfan Zheng、Jiaqiong Sun、Youwei Xu、Shuailei Zhai、Xingwei Li

  DOI：10.1002/anie.201900166

  日期：2019.4

  Pyridines/pyrimidines are common and effective directing groups in C−H activation. However, they are poorly functionalizable heteroarenes. Reported in this work is Mn‐catalyzed dehydrocyanative transannulation between three classes of heteroarenes and propargyl carbonates. The pyridyl/pyrimidyl groups in the heteroarenes initially function as directing groups to enable C−H allenylation; they then undergo

  吡啶/嘧啶是CH活化中常见的有效引导基团。但是，它们是功能差的杂芳烃。这项工作报告的是三类杂芳烃和碳酸炔丙酯之间的锰催化脱氢氰基转移环。杂芳烃中的吡啶基/嘧啶基最初起使CH烯丙基化的引导基团的作用。然后，它们与烯丙基部分进行分子内Diels–Alder / retroDiels–Alder反应，生成稠合的碳/杂环。分离了反应不同阶段的三个关键中间体。
• Manganese(I)-Catalyzed Synthesis of Fused Eight- and Four-Membered Carbocycles via C–H Activation and Pericyclic Reactions
  作者：Youwei Xu、Guangfan Zheng、Lingheng Kong、Xingwei Li

  DOI：10.1021/acs.orglett.9b01139

  日期：2019.5.3

  facile construction of complex cycles. On the other hand, metal-catalyzed C–H activation has been established as an important strategy for rapid synthesis of complex structures. The two areas are integrated in Mn(I)-catalyzed redox-neutral coupling of 3-alkenyl- and 3-allylindoles with propargylic carbonates, which occurred via C–H allenylation with subsequent pericyclic reactions to afford fused eight-

  周环反应使得可以容易地构建复杂的循环。另一方面，金属催化的C–H活化已被确立为快速合成复杂结构的重要策略。这两个区域都整合在了Mn（I）催化的3-烯基和3-烯丙醇的氧化还原-中性偶合与炔丙基碳酸酯中，这是通过C-H烯基化和随后的周环反应发生的，从而得到稠合的八元和四元碳环， 分别。
• Deoxygenative Silylation of C(sp³)–O Bonds with Hydrosilane by Cooperative Catalysis of Gold Nanoparticles and Solid Acids
  作者：Hiroki Miura、Yuki Yasui、Yosuke Masaki、Masafumi Doi、Tetsuya Shishido

  DOI：10.1021/acscatal.3c00973

  日期：2023.5.19

  Efficient deoxygenative silylation of C(sp3)–O bonds with hydrosilanes by supported Au catalysts is described. Gold nanoparticles supported on TiO2 enabled various hydrosilanes to be used as sources of silyl groups in C–Si cross-coupling reactions. A variety of alkyl acetates and propargyl carbonates participated in the Au-catalyzed reactions to furnish the corresponding alkyl and allenylsilanes in

  描述了负载型 Au 催化剂对 C(sp 3 )–O 键与氢硅烷的有效脱氧硅烷化。负载在 TiO 2上的金纳米粒子使各种氢硅烷能够在 C-Si 交叉偶联反应中用作甲硅烷基的来源。各种乙酸烷基酯和碳酸炔丙酯参与了金催化的反应，以高产率提供相应的烷基和烯丙基硅烷。此外，Au/TiO 2对环醚的开环甲硅烷基化也有效。详细的机理研究证实标题反应涉及甲硅烷基和烷基自由基中间体的形成，而 Au 纳米颗粒作为单电子转移催化剂与金属氧化物表面的路易斯酸位点的合作是氢硅烷异常反应性的原因特定的 C(sp 3 )–Si 键形成。