1-(2-Bromo-allyl)-2-oxo-cyclopentanecarboxylic acid ethyl ester | 156141-12-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1-(2-Bromo-allyl)-2-oxo-cyclopentanecarboxylic acid ethyl ester
• 英文别名: Ethyl 1-(2-bromoprop-2-enyl)-2-oxocyclopentane-1-carboxylate
• CAS: 156141-12-7
• 化学式: C₁₁H₁₅BrO₃
• 分子量: 275.142
• InChiKey: GMOQPZUNNUYEII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  三甲基(苯基)锡 、 1-(2-Bromo-allyl)-2-oxo-cyclopentanecarboxylic acid ethyl ester 在 四(三苯基膦)钯 、 lithium chloride 作用下， 以 1,4-二氧六环 为溶剂， 以76%的产率得到2-Oxo-1-(2-phenyl-allyl)-cyclopentanecarboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis of Stereodefined Polysubstituted Olefins. 1. Sequential Intermolecular Reactions Involving Selective, Stepwise Insertion of Pd(0) into Allylic and Vinylic Halide Bonds. The Stereoselective Synthesis of Disubstituted Olefins¹

  摘要：

  Palladium-catalyzed allylic substitution and cross-coupling reactions have been combined into a sequential procedure to provide a range of disubstituted olefin products starting from two-, three-, and four-carbon common olefin templates. Diverse application of this template strategy is demonstrated in a variety of model studies and in a parallel synthesis (combinatorial) approach to prepare an allylic amine molecular library. An approach toward the preparation of astaxanthin beta -D-diglucoside, an interesting antioxidant whose total synthesis has yet to be reported, using the olefin-template approach is also discussed.

  DOI：

  10.1021/jo001045l
• 作为产物：
  描述：

  2-氧代环戊羧酸乙酯 、 2,3-二溴-1-丙烯 在 sodium hydride 、 四(三苯基膦)钯 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.25h， 以92%的产率得到1-(2-Bromo-allyl)-2-oxo-cyclopentanecarboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis of Stereodefined Polysubstituted Olefins. 1. Sequential Intermolecular Reactions Involving Selective, Stepwise Insertion of Pd(0) into Allylic and Vinylic Halide Bonds. The Stereoselective Synthesis of Disubstituted Olefins¹

  摘要：

  Palladium-catalyzed allylic substitution and cross-coupling reactions have been combined into a sequential procedure to provide a range of disubstituted olefin products starting from two-, three-, and four-carbon common olefin templates. Diverse application of this template strategy is demonstrated in a variety of model studies and in a parallel synthesis (combinatorial) approach to prepare an allylic amine molecular library. An approach toward the preparation of astaxanthin beta -D-diglucoside, an interesting antioxidant whose total synthesis has yet to be reported, using the olefin-template approach is also discussed.

  DOI：

  10.1021/jo001045l

文献信息

• Synthesis of oxo-2-alkenylboronates and their cyclization to 3-methylene cycloalkanols via intramolecular allylboration
  作者：Takeo Watanabe、Masaaki Sakai、Norio Miyaura、Akira Suzuki

  DOI：10.1039/c39940000467

  日期：——

  The cross-coupling reaction between halocarbonyl compounds with Knochel's (dialkoxyboryl)methylzinc reagent provided a new synthesis of oxoalk-2-enylboronates; the in situ cyclization of these boronates gave 3-methylene cyclopentanols or cycloheptanols in high yields.

  卤代羰基化合物与 Knochel 的（二烷氧基硼酰）甲基锌试剂之间的交叉偶联反应提供了一种新的氧代烷基-2-烯基硼酸酯的合成方法；这些硼酸酯的原位环化反应能以高产率得到 3-亚甲基环戊醇或环庚醇。
• Synthesis of Stereodefined Polysubstituted Olefins. 1. Sequential Intermolecular Reactions Involving Selective, Stepwise Insertion of Pd(0) into Allylic and Vinylic Halide Bonds. The Stereoselective Synthesis of Disubstituted Olefins¹
  作者：Michael G. Organ、Jeremy T. Cooper、Lawrence R. Rogers、Fariba Soleymanzadeh、Timothy Paul

  DOI：10.1021/jo001045l

  日期：2000.11.1

  Palladium-catalyzed allylic substitution and cross-coupling reactions have been combined into a sequential procedure to provide a range of disubstituted olefin products starting from two-, three-, and four-carbon common olefin templates. Diverse application of this template strategy is demonstrated in a variety of model studies and in a parallel synthesis (combinatorial) approach to prepare an allylic amine molecular library. An approach toward the preparation of astaxanthin beta -D-diglucoside, an interesting antioxidant whose total synthesis has yet to be reported, using the olefin-template approach is also discussed.