3-氧代环庚烷羧酸乙酯 | 50559-00-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 3-氧代环庚烷羧酸乙酯
• 英文名称: ethyl 3-oxocycloheptanecarboxylate
• 英文别名: ethyl 3-oxocycloheptane-1-carboxylate
• CAS: 50559-00-7
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: OYORJLDSVLYYBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2918300090

反应信息

• 作为产物：
  描述：

  ethyl 1-(iodomethyl)-2-oxocyclohexanecarboxylate 在 nickel(II) iodide 、 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 生成 3-氧代环庚烷羧酸乙酯
  参考文献：
  名称：

  Facile Ring Expansions of α-Halomethyl β-Keto Esters Mediated with SmI2

  摘要：

  用SmI2处理α-卤甲基β-酮酯，在HMPA或NiI2的帮助下得到了相应的一碳扩展产物。

  DOI：

  10.1055/s-2001-16064

文献信息

• Novel free radical ring-expansion reactions
  作者：Paul Dowd、Soo-Chang Choi

  DOI：10.1016/0040-4020(89)80035-3

  日期：1989.1

  A novel free radical initiated ring expansion of haloalkyl β-keto esters is described. Following alkylation of the β-keto ester with the appropriate dihalide, the resulting halide is treated at reflux with tri-n-butyltin hydride. Rearrangement to the homologated γ-keto ester occurs smoothly. An oxy radical intermediate is proposed for the reaction.

  描述了卤代烷基β-酮酯的新颖的自由基引发的环膨胀。用适当的二卤化物将β-酮酯烷基化后，将所得的卤化物用氢化三正丁基锡进行回流处理。平稳地重排成均相的γ-酮酯。提出了一种氧自由基中间体用于该反应。
• Photoinduced Electron Transfer Promoted Radical Ring Expansion and Cyclization Reactions of α-(ω-Carboxyalkyl) β-Keto Esters
  作者：Keisuke Nishikawa、Tomoki Ando、Kousuke Maeda、Toshio Morita、Yasuharu Yoshimi

  DOI：10.1021/ol303460u

  日期：2013.2.1

  Photoinduced electron transfer (PET) promoted decarboxylation of α-(ω-carboxyalkyl) β-keto esters undergoes radical ring expansion and cyclization reactions. This mild and environmentally friendly method can provide one-carbon expanded γ-keto esters and bicyclic alcohols, and the product distribution is strongly dependent on the length of the alkyl chain containing the terminal carboxylate group.

  光诱导电子转移（PET）促进α-（ω-羧烷基）β-酮酯的脱羧反应经历自由基扩环和环化反应。这种温和且环保的方法可提供单碳膨胀的γ-酮酯和双环醇，并且产物的分布在很大程度上取决于包含末端羧酸酯基团的烷基链的长度。
• Electrochemical Reduction of 1-Bromomethyl-2-oxocycloalkane-1-carboxylates at Silver Cathodes in Dimethylformamide: One-Carbon Ring-Expansion Reactions
  作者：Ethan A. Wappes、Mohammad S. Mubarak、Dennis G. Peters

  DOI：10.1149/2.0491414jes

  日期：——

  O have revealed that carbanion intermediatesresult in small amounts from two-electron cleavage of carbon–bromine bonds. A mechanistic scheme, involving both radicals andcarbanions, is proposed to account for the formation of the various products.© The Author(s) 2014. Published by ECS. This is an open access article distributed under the terms of the Creative CommonsAttribution 4.0 License (CC BY,

  O 揭示了碳负离子中间体产生少量来自碳 - 溴键的双电子裂解。提出了一种涉及自由基和碳负离子的机制方案来解释各种产物的形成。© The Author(s) 2014。由 ECS 出版。这是一篇根据知识共享署名 4.0 许可（CC BY，http://creativecommons.org/licenses/by/4.0/）的条款分发的开放获取文章，它允许在任何媒体上不受限制地重复使用该作品，前提是原始作品被正确引用。[DOI: 10.1149/2.0491414jes] 版权所有，2014 年 8 月 11 日投稿；修订稿于 2014 年 9 月 26 日收到。2014 年 10 月 7 日发表。
• Green molecular transformation by a B12–TiO2 hybrid catalyst as an alternative to tributyltin hydride
  作者：Hisashi Shimakoshi、Makoto Abiru、Shin-ichiro Izumi、Yoshio Hisaeda

  DOI：10.1039/b913255d

  日期：——

  The B12–TiO2 hybrid catalyst was effectively used for the radical reactions, such as 1,2-migrations of phenyl groups and acyl groups under irradiation by UV light, and the selectivity of the reaction was controlled by the solvent system.

  B12-TiO2混合催化剂被有效地用于自由基反应，例如苯基和酰基在紫外光照射下的1,2-迁移，反应的选择性由溶剂体系控制。
• Environmentally friendly TPDS-mediated free radical ring expansion of α-haloalkyl cyclic β-keto esters
  作者：Masaaki Sugi、Hideo Togo

  DOI：10.1016/s0040-4020(02)00241-7

  日期：2002.4

  Reactivities of tetraphenyldisilane (TPDS), tris(trimethylsilyl)silane, and tributyltin hydride in the radical ring expansion of α-haloalkyl cyclic β-keto esters were examined. Among these reagents, TPDS was found most effective for the preparation of medium-sized cyclic compounds in terms of yields and ring-expansion/reduction selectivity.

  考察了四苯基二硅烷 (TPDS)、三（三甲基甲硅烷基）硅烷和三丁基氢化锡在 α-卤代烷基环状 β-酮酯自由基扩环中的反应性。在这些试剂中，发现 TPDS 在产率和扩环/还原选择性方面对制备中等大小的环状化合物最有效。