diethyl 1-oxo-1H-indene-2,2(3H)-dicarboxylate | 122951-09-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: diethyl 1-oxo-1H-indene-2,2(3H)-dicarboxylate
• 英文别名: 3-oxo-1H-indene-2,2-dicarboxylic acid diethyl ester；diethyl 3-oxo-1H-indene-2,2-dicarboxylate
• CAS: 122951-09-1
• 化学式: C₁₅H₁₆O₅
• 分子量: 276.289
• InChiKey: CHCCRGMGXBHMIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  2-(1,3-dioxolan-2-yl)benzaldehyde 在 哌啶 、 溶剂黄146 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 2.0h， 生成 diethyl 1-oxo-1H-indene-2,2(3H)-dicarboxylate
  参考文献：
  名称：

  三氟甲磺酸Scan催化的分子内氧化还原反应对乙酸C（sp3）-H键的功能化：串联1,4-氢化物转移/ 1,5-环化过程导致被保护的1-茚满酮

  摘要：

  报道了一种新的CC键形成反应，该反应导致相邻的季碳原子。它是由缩醛C的hydricity促进一釜氢化物转变/环化过程 H键，用benzylidenemalonate片段作为电子受体氢化物，和钪（III），三氟甲磺酸的催化作用。反应产物是1,2-二氢茚满衍生物。烷氧基和链烷硫醇酯基团也可以从缩醛碳分子内转移到亲电的亚苄基丙二酸酯CC键上。

  DOI：

  10.1002/adsc.201000812

文献信息

• Concise synthesis of cyclic carbonyl compounds from haloarenes using phenyl formate as the carbonyl source
  作者：Hideyuki Konishi、Hiroki Nagase、Kei Manabe

  DOI：10.1039/c4cc09413a

  日期：——

  Carbonylative cyclization of haloarenes bearing nucleophilic moieties under Pd catalysis has been developed as a general, user-friendly method for access to various cyclic carbonyl compounds.

  在钯催化下，含有亲核基团的卤代芳烃的羰基化环化已经发展成为获取各种环状羰基化合物的一种通用、用户友好的方法。

• 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.
• Catalytic generation and trapping of acylmetals containing Ni and Cu with enolates
  作者：Ei-ichi Negishi、Hidefumi Makabe、Izumi Shimoyama、Guangzhong Wu、Yantao Zhang

  DOI：10.1016/s0040-4020(97)10210-1

  日期：1998.2

  Carbonylative cyclization of iodoarenes and iodoalkenes containing a proximal enolate precursor can selectively provide either cyclic ketones or lactones in the presence of Ni or Cu catalysts via trapping of putative acylmetal derivatives with C-or O-enolates, respectively; the ring size and regioselectivity of the reaction may be predicted based on two generalizations derived from the recently developed corresponding Pd-catalyzed reaction. (C) 1998 Elsevier Science Ltd. 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