5,7,8,9-tetrahydro-5-oxo-6H-benzocycloheptene-6,6-dicarboxylic acid diethyl ester | 122951-02-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,7,8,9-tetrahydro-5-oxo-6H-benzocycloheptene-6,6-dicarboxylic acid diethyl ester
• 英文别名: diethyl 5-oxo-8,9-dihydro-5H-benzo[7]annulene-6,6(7H)-dicarboxylate；7,7-bis(ethoxycarbonyl)-2,3-benzo-2-cyclohepten-1-one；diethyl 5-oxo-8,9-dihydro-7H-benzo[7]annulene-6,6-dicarboxylate
• CAS: 122951-02-4
• 化学式: C₁₇H₂₀O₅
• 分子量: 304.343
• InChiKey: IIBPTKDVNXYIMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-(3-bromopropyl)-2-iodobenzene 在 bis-triphenylphosphine-palladium(II) chloride 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 100.0 ℃ 、4.14 MPa 条件下， 生成 5,7,8,9-tetrahydro-5-oxo-6H-benzocycloheptene-6,6-dicarboxylic acid diethyl ester
  参考文献：
  名称：

  Palladium-catalyzed carbonylative cyclization via trapping of acylpalladium derivatives with internal enolates. Its scope and factors affecting the C-to-O ratio

  摘要：

  The Pd-catalyzed carbonylative cyclization reaction involving omega-acyl-substituted acylpalladium derivatives can proceed via intramolecular trapping with either C- or O-enolates; the preferential formation of either 5- or 6-membered rings dictates the C-to-O ratio in the trapping with enolates.

  DOI：

  10.1016/s0040-4020(01)80765-1

文献信息

• CO Gas‐free Intramolecular Cyclocarbonylation Reactions of Haloarenes Having a C‐Nucleophile through CO‐Relay between Rhodium and Palladium
  作者：Tsumoru Morimoto、Mana Yamashita、Ai Tomiie、Hiroki Tanimoto、Kiyomi Kakiuchi

  DOI：10.1002/asia.201901595

  日期：2020.2.17

  We describe transfer carbonylation reactions of 2‐bromoarenes that contain a carbon‐nucleophile using aldehydes as a substitute for CO, leading to the formation of indanone derivatives. The transformation proceeds efficiently under RhI/Pd0‐hybrid catalytic conditions consisting of two discrete transition metals, rhodium and palladium, which catalyze the decarbonylation of aldehydes and the subsequent

  我们描述了使用醛代替CO的含碳亲核试剂的2-溴代芳烃的转移羰基化反应，从而导致茚满酮衍生物的形成。在由两种离散过渡金属铑和钯组成的Rh I / Pd 0混合催化条件下，该转化有效地进行，这两种催化金属分别催化醛的脱羰作用和随后使用所得羰基部分进行的溴代芳烃的羰基化。大部分提取的CO均通过从铑到钯的CO中继过程直接转移到产品中。
• Rh(I)-catalyzed CO gas-free carbonylative cyclization of organic halides with tethered nucleophiles using aldehydes as a substitute for carbon monoxide
  作者：Tsumoru Morimoto、Masahiko Fujioka、Koji Fuji、Ken Tsutsumi、Kiyomi Kakiuchi

  DOI：10.1016/j.jorganchem.2006.08.038

  日期：2007.1

  The CO gas-free carbonylative cyclization of organic halides, with tethered nitrogen, oxygen, and carbon nucleophiles, with aldehydes as a substitute for carbon monoxide can be achieved in the presence of a catalytic amount of a rhodium complex. The reaction involves the decarbonylation of the aldehyde by the rhodium catalyst, and the successive carbonylation of an organic halide utilizing the rhodium carbonyl that is formed in situ. Aldehydes having electron-withdrawing groups showed a higher ability to donate the carbonyl moiety. (c) 2006 Elsevier B.V. All rights reserved.
• Carbonylative cyclization via intramolecular trapping of acylmetal derivatives by carbon nucleophiles catalyzed by late transition metals
  作者：Eiichi Negishi、Yantao Zhang、Izumi Shimoyama、Guangzhong Wu

  DOI：10.1021/ja00202a055

  日期：1989.9
• NEGISHI, EI-ICHI;ZHANG, YANTAO;SHIMOYAMA, IZUMI;WU, GUANGZHONG, J. AMER. CHEM. SOC., 111,(1989) N0, C. 8018-8020
  作者：NEGISHI, EI-ICHI、ZHANG, YANTAO、SHIMOYAMA, IZUMI、WU, GUANGZHONG

  DOI：——

  日期：——