1-Bromomethyl-2-oxo-1,2,3,4-tetrahydro-naphthalene-1-carboxylic acid ethyl ester | 142338-24-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-Bromomethyl-2-oxo-1,2,3,4-tetrahydro-naphthalene-1-carboxylic acid ethyl ester
• 英文别名: Ethyl 1-(bromomethyl)-2-oxo-3,4-dihydronaphthalene-1-carboxylate
• CAS: 142338-24-7
• 化学式: C₁₄H₁₅BrO₃
• 分子量: 311.175
• InChiKey: NFPHZYFTCQCFEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 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-1,2,3,4-tetrahydro-naphthalene-1-carboxylic acid ethyl ester 在 甲醇 、 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以90%的产率得到7-Oxo-6,7,8,9-tetrahydro-5H-benzocycloheptene-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  First example of samarium diiodide-promoted sequential cyclization and ring-expansion reactions of α-bromomethyl cyclic β-keto esters to homologated γ-keto esters

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(98)00658-3
• 作为产物：
  描述：

  ethyl 2-tetralone-1-carboxylate 、 二溴甲烷 在 sodium hydride 作用下， 生成 1-Bromomethyl-2-oxo-1,2,3,4-tetrahydro-naphthalene-1-carboxylic acid ethyl ester
  参考文献：
  名称：

  Ring expansion of benzocyclic ketones via transient alkoxyl radicals: The side chain incorporation approach

  摘要：

  DOI：

  10.1016/s0040-4020(01)88482-9

文献信息

• Tris(trimethylsilyl)silane promoted radical reaction and electron-transfer reaction in benzotrifluoride
  作者：Eietsu Hasegawa、Yuki Ogawa、Koji Kakinuma、Hiroyuki Tsuchida、Emi Tosaka、Shinya Takizawa、Hiroyasu Muraoka、Tomoko Saikawa

  DOI：10.1016/j.tet.2008.06.012

  日期：2008.8

  Tris(trimethylsilyl)silane (TTMSS) promoted free radical reaction in benzotrifluoride (BTF) was investigated. Compared to same reaction using environmentally less desirable tri-n-butyltin hydride (TBTH) in benzene, less quantity of BTF than that of benzene can be used because of slower hydrogen atom transfer from TTMSS than that from TBTH toward primary alkyl radicals. Also, electron-transfer reactions

  研究了三（三甲基甲硅烷基）硅烷（TTMSS）在苯并三氟化物（BTF）中促进的自由基反应。使用环境不太理想的三-相对于相同的反应Ñ苯-butyltin氢化物（TBTH），BTF的比苯的可以因为来自TTMSS较慢氢原子转移比从TBTH朝向初级烷基的使用量较少。另外，在BTF中进行了由三（对-溴苯基）六氯锑酸铵（TBPA）和FeCl 3促进的电子转移反应。然后，发现TBPA在BTF中的效果与在二氯甲烷中的效果相当。另外，有趣的观察表明FeCl 3加入咪唑鎓盐可促进反应的进行。所有结果表明，BTF是与TTMSS进行自由基反应和使用TBPA以及FeCl 3进行电子转移反应的可耐受溶剂。
• 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.
• Ring expansion of benzocyclic ketones via transient alkoxyl radicals: The side chain incorporation approach
  作者：W. Russell Bowman、Paul J. Westlake

  DOI：10.1016/s0040-4020(01)88482-9

  日期：1992.1