diethyl 5-acetylindan-2,2-dicarboxylate | 214150-19-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: diethyl 5-acetylindan-2,2-dicarboxylate
• 英文别名: 2H-Indene-2,2-dicarboxylic acid, 5-acetyl-1,3-dihydro-, diethyl ester；diethyl 5-acetyl-1,3-dihydroindene-2,2-dicarboxylate
• CAS: 214150-19-3
• 化学式: C₁₇H₂₀O₅
• 分子量: 304.343
• InChiKey: QJVTYLADDUSXJI-UHFFFAOYSA-N

物化性质

• 沸点：
  406.4±45.0 °C(Predicted)
• 密度：
  1.185±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  7
• 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

• 作为反应物：
  描述：

  2-甲基丙烯醛 、 diethyl 5-acetylindan-2,2-dicarboxylate 在 nickel dichloride 、 锌 三乙胺 、 zinc(II) chloride 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以65%的产率得到diethyl 6H-5-formyl-5-methylindan-2,2-dicarboxylate
  参考文献：
  名称：

  Nickel- and Zinc-Promoted [2 + 2 + 2] Cycloaddition of Diynes and α,β-Enones

  摘要：

  The [2 + 2 + 2] cycloaddition of diynes and enones occurred in the presence of both nickel and zinc together. This binary metal-mediated reaction had two interesting features: (1) a terminally unsubstituted diyne reacted with an enone to give an aromatic compound with the concomitant incorporation of two hydrogen atoms abstracted from an expected 1,S-diene product into another molecule of the starting enone and (2) a trimethylsilyl-substituted diyne reacted with an equimolar amount of enone to regioselectively afford a 1,3-diene, in which the trimethylsilyl group is adjacent to the carbonyl group.

  DOI：

  10.1021/jo980987b
• 作为产物：
  描述：

  diethyl 5-acetyl-2,3,5,6-tetrahydro-1H-2,2-indenedicarboxylate 在 silica gel 作用下， 以70%的产率得到diethyl 5-acetylindan-2,2-dicarboxylate
  参考文献：
  名称：

  镍配合物催化α，β-不饱和羰基化合物与炔烃的高度区域选择性和立体选择性共环三聚和线性共聚。

  摘要：

  环烯酮2-环己烯-1-酮（1a），4,4-二甲基-2-环己烯-1-酮（1b），2-环戊烯-1-酮（1c）和2-环庚烯-1-酮（ 1d）与Ni（PPh（3））（2）I（2），ZnI（2）和Zn粉在62°C下在THF中与octa-1,7-diyne（2）反应，得到[ [2 + 2 + 2]环加成-脱氢产物3a-d的产率为32-80％。对α，β-不饱和内酯5a（5,6-二氢-2H-吡喃-2-酮）进行[2 + 2 + 2]环加成反应，得到2相应的环己二烯产物6（29％）和脱氢产物7（ 39％）。在相似的反应条件下，3-丁烯-2-酮与2和各种取代的庚-1,6-二炔9a-c反应，以68-80％的产率得到[2 + 2 + 2]环加成-脱氢产物11a-d 。二苯乙炔也可与1a-d，5a反应，和2（5H）-呋喃酮（5b），得到相应的[2 + 2 + 2]共环三聚产物13a-d和14a-b。在反应和后处理条件

  DOI：

  10.1021/jo9900580

文献信息

• Intramolecular Rhodium-Catalyzed [2+2+2] Cyclizations of Diynes with Enones
  作者：Amanda L. Jones、John K. Snyder

  DOI：10.1021/jo9001678

  日期：2009.4.3

  The Rh(I)-catalyzed inter- and intramolecular [2+2+2] cyclization of diynes with alpha,beta-unsaturated enones proceeds with microwave promotion in good yields. This chemistry was applied to the synthesis of (-)-alcyopterosin I.
• Nickel- and Zinc-Promoted [2 + 2 + 2] Cycloaddition of Diynes and α,β-Enones
  作者：Shin-ichi Ikeda、Hitomi Watanabe、Yoshiro Sato

  DOI：10.1021/jo980987b

  日期：1998.10.1

  The [2 + 2 + 2] cycloaddition of diynes and enones occurred in the presence of both nickel and zinc together. This binary metal-mediated reaction had two interesting features: (1) a terminally unsubstituted diyne reacted with an enone to give an aromatic compound with the concomitant incorporation of two hydrogen atoms abstracted from an expected 1,S-diene product into another molecule of the starting enone and (2) a trimethylsilyl-substituted diyne reacted with an equimolar amount of enone to regioselectively afford a 1,3-diene, in which the trimethylsilyl group is adjacent to the carbonyl group.
• Highly Regio- and Stereoselective Cocyclotrimerization and Linear Cotrimerization of α,β-Unsaturated Carbonyl Compounds with Alkynes Catalyzed by Nickel Complexes
  作者：Thota Sambaiah、Lih-Ping Li、Daw-Jen Huang、Cheng-Hong Lin、Dinesh Kumar Rayabarapu、Chien-Hong Cheng

  DOI：10.1021/jo9900580

  日期：1999.5.1

  degrees C affords the corresponding conjugated trienes 17a-c in 82-92% yields. The MS data of 17firmly support an adduct of two molecules of alkyne and a molecule of acrylate. Similarly, the reaction of 15a with octa-1,7-diyne in the presence of Ni(PPh(3))(2)I(2), ZnI(2), and zinc gives triene derivative 21 in 68% yield. NOE and X-ray results indicate that in these trienes the substituents from each alkyne

  环烯酮2-环己烯-1-酮（1a），4,4-二甲基-2-环己烯-1-酮（1b），2-环戊烯-1-酮（1c）和2-环庚烯-1-酮（ 1d）与Ni（PPh（3））（2）I（2），ZnI（2）和Zn粉在62°C下在THF中与octa-1,7-diyne（2）反应，得到[ [2 + 2 + 2]环加成-脱氢产物3a-d的产率为32-80％。对α，β-不饱和内酯5a（5,6-二氢-2H-吡喃-2-酮）进行[2 + 2 + 2]环加成反应，得到2相应的环己二烯产物6（29％）和脱氢产物7（ 39％）。在相似的反应条件下，3-丁烯-2-酮与2和各种取代的庚-1,6-二炔9a-c反应，以68-80％的产率得到[2 + 2 + 2]环加成-脱氢产物11a-d 。二苯乙炔也可与1a-d，5a反应，和2（5H）-呋喃酮（5b），得到相应的[2 + 2 + 2]共环三聚产物13a-d和14a-b。在反应和后处理条件