2-cyano-2,3-dihydro-1-oxo-2H-indene-2-carboxylic acid ethyl ester | 122951-00-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2-cyano-2,3-dihydro-1-oxo-2H-indene-2-carboxylic acid ethyl ester
• 英文别名: ethyl 2-cyano-1-oxo-2,3-dihydro-1H-indene-2-carboxylate；ethyl 2-cyano-3-oxo-1H-indene-2-carboxylate
• CAS: 122951-00-2
• 化学式: C₁₃H₁₁NO₃
• 分子量: 229.235
• InChiKey: DTNVZCQNHNDAFZ-UHFFFAOYSA-N

物化性质

• 熔点：
  51-52 °C
• 沸点：
  394.7±42.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  67.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  五氟苯甲醛 、 苯丙酸,a-氰基-2-碘-,乙基酯 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 1,3-双(二苯基膦)丙烷 potassium carbonate 作用下， 以 xylene 为溶剂， 反应 24.0h， 以51%的产率得到2-cyano-2,3-dihydro-1-oxo-2H-indene-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  Rh(I)-catalyzed CO gas-free carbonylative cyclization of organic halides with tethered nucleophiles using aldehydes as a substitute for carbon monoxide

  摘要：

  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.

  DOI：

  10.1016/j.jorganchem.2006.08.038

文献信息

• The direct electrophilic cyanation of β-keto esters and amides with cyano benziodoxole
  作者：Yao-Feng Wang、Jiashen Qiu、Dejie Kong、Yongtao Gao、Feipeng Lu、Pran Gopal Karmaker、Fu-Xue Chen

  DOI：10.1039/c4ob02032d

  日期：——

  Electrophilic cyanating agent C1 accomplishes the direct cyanation of β-keto esters and amides without any catalyst and base.

  电亲电性氰化试剂C1实现了β-酮酯和酰胺的直接氰化，无需任何催化剂和碱。
• 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
• 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：——
• 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.