1-Bromomethyl-2-oxo-cycloheptanecarboxylic acid ethyl ester | 129104-37-6

• 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
• 英文名称: 1-Bromomethyl-2-oxo-cycloheptanecarboxylic acid ethyl ester
• 英文别名: Ethyl 1-(bromomethyl)-2-oxocycloheptane-1-carboxylate
• CAS: 129104-37-6
• 化学式: C₁₁H₁₇BrO₃
• 分子量: 277.158
• InChiKey: YGUJUDVVEUULFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-Bromomethyl-2-oxo-cycloheptanecarboxylic acid ethyl ester 在 cyanoaquacobyrinic acid immobilized on TiO₂ 作用下， 以 乙醇 为溶剂， 反应 13.0h， 以80%的产率得到3-氧代环辛烷-1-羧酸乙酯
  参考文献：
  名称：

  Green molecular transformation by a B12–TiO2 hybrid catalyst as an alternative to tributyltin hydride

  摘要：

  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。

  DOI：

  10.1039/b913255d

文献信息

• Visible-light-driven palladium-catalyzed Dowd–Beckwith ring expansion/C–C bond formation cascade
  作者：Li Chen、Li-Na Guo、Shuai Liu、Le Liu、Xin-Hua Duan

  DOI：10.1039/d0sc04399k

  日期：——

  palladium-catalyzed Dowd–Beckwith ring expansion/C–C bond formation cascade is described. A range of six to nine-membered β-alkenylated cyclic ketones possessing a quaternary carbon center were accessed under mild conditions. Besides styrenes, the electron-rich alkenes such as silyl enol ethers and enamides were also compatible, providing the desired β-alkylated cyclic ketones in moderate to good yields.

  描述了可见光诱导的钯催化的 Dowd-Beckwith 环扩展/C-C 键形成级联。在温和条件下获得了一系列具有季碳中心的六至九元β-烯基化环酮。除苯乙烯外，富电子烯烃（例如甲硅烷基烯醇醚和烯酰胺）也相容，以中等至良好的产率提供所需的β-烷基化环酮。
• First example of samarium diiodide-promoted sequential cyclization and ring-expansion reactions of α-bromomethyl cyclic β-keto esters to homologated γ-keto esters
  作者：Eietsu Hasegawa、Takashi Kitazume、Kimiko Suzuki、Emi Tosaka

  DOI：10.1016/s0040-4039(98)00658-3

  日期：1998.6

  SmI2 reductions of some aromatic as well as aliphatic alpha-bromomethyl cyclic beta-keto esters produced one-carbon homologated gamma-keto esters in modest to good yields. (C) 1998 published by Elsevier Science Ltd. All rights reserved.
• Electroorganic chemistry. 124. Electroreductive intramolecular coupling of .alpha.-(.omega.-bromoalkyl) .beta.-keto esters
  作者：Tatsuya Shono、Naoki Kise、Nobuyuki Uematsu、Shinji Morimoto、Eiichi Okazaki

  DOI：10.1021/jo00304a014

  日期：1990.8
• Reductive transformation of α,β-epoxy ketones and other compounds promoted through photoinduced electron transfer processes with 1,3-dimethyl-2-phenylbenzimidazoline (DMPBI)
  作者：Eietsu Hasegawa、Akira Yoneoka、Kumiko Suzuki、Teru Kato、Takashi Kitazume、Kazuhiro Yanagi

  DOI：10.1016/s0040-4020(99)00804-2

  日期：1999.11

  Photoreactions of epoxy ketones, aromatic ketones, haloketones, and aromatic halides with 1,3-dimethyl-2-phenylbenzimidazoline (DMPBI) were studied Photoinduced single-electron transfer from DMPBI to such substrates initiates the reactions followed by radical radical rearrangement and reduction to finally give several reduced products in modest to good yields. (C) 1999 Elsevier Science Ltd. All rights reserved.
• SHONO, TATSUYA;KISE, NAOKI;UEMATSU, NOBUYUKI;MORIMOTO, SHINJI;OKAZAKI, EI+, J. ORG. CHEM., 55,(1990) N7, C. 5037-5041
  作者：SHONO, TATSUYA、KISE, NAOKI、UEMATSU, NOBUYUKI、MORIMOTO, SHINJI、OKAZAKI, EI+

  DOI：——

  日期：——