diethyl 7-oxo-8-trimethylsilylbicyclo[3.3.0]oct-1(8)-ene-3,3-dicarboxylate | 189949-44-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: diethyl 7-oxo-8-trimethylsilylbicyclo[3.3.0]oct-1(8)-ene-3,3-dicarboxylate
• 英文别名: diethyl 3,3a,4,5-tetrahydro-6-(trimethylsilyl)-5-oxopentalene-2,2(1H)-dicarboxylate；Diethyl 5-oxo-6-trimethylsilyl-1,3,3a,4-tetrahydropentalene-2,2-dicarboxylate
• CAS: 189949-44-8
• 化学式: C₁₇H₂₆O₅Si
• 分子量: 338.476
• InChiKey: XFGHVPPBHOPCHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.66
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  diethyl 7-oxo-8-trimethylsilylbicyclo[3.3.0]oct-1(8)-ene-3,3-dicarboxylate 在 palladium on activated charcoal 一氯化碘 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 水 为溶剂， 反应 6.0h， 生成 5-oxo-6-phenyl-3,3a,4,5-tetrahydro-1H-pentalene-2,2-dicarboxylic acid diethyl ester
  参考文献：
  名称：

  Practical and Efficient Suzuki−Miyaura Cross-Coupling of 2-Iodocycloenones with Arylboronic Acids Catalyzed by Recyclable Pd(0)/C

  摘要：

  The first Suzuki-Miyaura cross-coupling of 2-iodocycloenones with arylboronic acids catalyzed by 10% Pd(O)/C is described as an interesting alternative to classical homogeneous conditions. Most of the substrate reacted under mild condition at 25 degrees C under air in aqueous DME. The conditions described tolerate a wide range of iodoenones and boronic acids. Notably, the procedure features inexpensive reagents and solvents with low toxicity rendering the method environmentally benign. Additionally 10% Pd(O)/C could be recovered and efficiently reused at least five times without significant alteration of the yields of the cross-coupled product.

  DOI：

  10.1021/jo051501b
• 作为产物：
  描述：

  diethyl 2-allyl-2-(3-(trimethylsilyl)prop-2-yn-1-yl)malonate 、 alkaline earth salt of/the/ methylsulfuric acid 在 十二/十四烷基二甲基氧化胺 作用下， 以 乙醚 、 四氢呋喃 为溶剂， 反应 4.0h， 以80%的产率得到diethyl 7-oxo-8-trimethylsilylbicyclo[3.3.0]oct-1(8)-ene-3,3-dicarboxylate
  参考文献：
  名称：

  Practical and Efficient Suzuki−Miyaura Cross-Coupling of 2-Iodocycloenones with Arylboronic Acids Catalyzed by Recyclable Pd(0)/C

  摘要：

  The first Suzuki-Miyaura cross-coupling of 2-iodocycloenones with arylboronic acids catalyzed by 10% Pd(O)/C is described as an interesting alternative to classical homogeneous conditions. Most of the substrate reacted under mild condition at 25 degrees C under air in aqueous DME. The conditions described tolerate a wide range of iodoenones and boronic acids. Notably, the procedure features inexpensive reagents and solvents with low toxicity rendering the method environmentally benign. Additionally 10% Pd(O)/C could be recovered and efficiently reused at least five times without significant alteration of the yields of the cross-coupled product.

  DOI：

  10.1021/jo051501b

文献信息

• Rhodium-Catalyzed Intramolecular Pauson-Khand Reaction
  作者：Yuji Koga、Toshitake Kobayashi、Koichi Narasaka

  DOI：10.1246/cl.1998.249

  日期：1998.3

  A rhodium dinuclear carbonyl complex, [RhCl(CO)2]2, serves as a catalyst of the intramolecular Pauson-Khand reaction. 1,6-Enynes are converted to cyclopentenone derivatives in high yield by heating in the presence of the catalyst under an atmospheric pressure of CO.

  铑双核羰基络合物 [RhCl(CO)2]2 可作为分子内 Pauson-Khand 反应的催化剂。1,6-烯炔通过在催化剂的存在下在大气压的 CO 下加热以高产率转化为环戊烯酮衍生物。
• The rhodium-catalyzed Pauson–Khand reaction
  作者：Toshitake Kobayashi、Yuji Koga、Koichi Narasaka

  DOI：10.1016/s0022-328x(00)00835-4

  日期：2001.4

  A rhodium carbonyl complex, [RhCl(CO)(2)](2), serves as a catalyst of the intra- and inter-molecular Pauson-Khand reaction. By the use of the rhodium catalyst, cyclopentenone derivatives are prepared from various 1,6- and 1,7-enynes under 1 arm of CO. Furthermore, this rhodium-catalyzed reaction is accelerated by reducing partial pressure of CO to less than 1 atm. (C) 2001 Elsevier Science B.V. All rights reserved.
• Ru₃(CO)₁₂-Catalyzed Cyclocarbonylation of 1,6-Enynes to Bicyclo[3.3.0]octenones
  作者：Tsumoru Morimoto、Naoto Chatani、Yoshiya Fukumoto、Shinji Murai

  DOI：10.1021/jo970231x

  日期：1997.5.1
• First Ruthenium-Catalyzed Intramolecular Pauson−Khand Reaction
  作者：Teruyuki Kondo、Nobuyoshi Suzuki、Takumi Okada、Take-aki Mitsudo

  DOI：10.1021/ja970793y

  日期：1997.7.1
• Practical and Efficient Suzuki−Miyaura Cross-Coupling of 2-Iodocycloenones with Arylboronic Acids Catalyzed by Recyclable Pd(0)/C
  作者：François-Xavier Felpin

  DOI：10.1021/jo051501b

  日期：2005.10.1

  The first Suzuki-Miyaura cross-coupling of 2-iodocycloenones with arylboronic acids catalyzed by 10% Pd(O)/C is described as an interesting alternative to classical homogeneous conditions. Most of the substrate reacted under mild condition at 25 degrees C under air in aqueous DME. The conditions described tolerate a wide range of iodoenones and boronic acids. Notably, the procedure features inexpensive reagents and solvents with low toxicity rendering the method environmentally benign. Additionally 10% Pd(O)/C could be recovered and efficiently reused at least five times without significant alteration of the yields of the cross-coupled product.