1-(trifluoromethyl)cyclopent-3-enecarboxylic acid | 1374328-81-0

• 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: 1-(trifluoromethyl)cyclopent-3-enecarboxylic acid
• 英文别名: 1-(Trifluoromethyl)-3-cyclopentene-1-carboxylic acid；1-(trifluoromethyl)cyclopent-3-ene-1-carboxylic acid
• CAS: 1374328-81-0
• 化学式: C₇H₇F₃O₂
• 分子量: 180.127
• InChiKey: TXUTULIFFMGNRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(trifluoromethyl)cyclopent-3-enecarboxylic acid 在 bis(norbornadiene)rhodium(l)tetrafluoroborate 、 草酰氯 、 4,4,6-trimethyl-1,3,2-dioxaborinane 、 N-benzyl-N-phenyl-12,14-dioxa-13-phosphapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2(11),3,5,7,9,16,18,20,22-decaen-13-amine 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 (1S,3S)-3-hydroxy-1-(trifluoromethyl)cyclopentanecarboxylic acid benzyl amide
  参考文献：
  名称：

  Enantioselective Desymmetrization via Carbonyl-Directed Catalytic Asymmetric Hydroboration and Suzuki–Miyaura Cross-Coupling

  摘要：

  The rhodium-catalyzed enantioselective desymmetrization of symmetric gamma,delta-unsaturated amides via carbonyl-directed catalytic asymmetric hydroboration (directed CAHB) affords chiral secondary organoboronates with up to 98% ee. The chiral gamma-borylated products undergo palladium-catalyzed Suzuki-Miyaura cross-coupling via the trifluoroborate salt with stereoretention.

  DOI：

  10.1021/ol503764d
• 作为产物：
  描述：

  benzyl 1-(trifluoromethyl)cyclopent-3-enecarboxylate 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 1-(trifluoromethyl)cyclopent-3-enecarboxylic acid
  参考文献：
  名称：

  Enantioselective Desymmetrization via Carbonyl-Directed Catalytic Asymmetric Hydroboration and Suzuki–Miyaura Cross-Coupling

  摘要：

  The rhodium-catalyzed enantioselective desymmetrization of symmetric gamma,delta-unsaturated amides via carbonyl-directed catalytic asymmetric hydroboration (directed CAHB) affords chiral secondary organoboronates with up to 98% ee. The chiral gamma-borylated products undergo palladium-catalyzed Suzuki-Miyaura cross-coupling via the trifluoroborate salt with stereoretention.

  DOI：

  10.1021/ol503764d

文献信息

• 1-(Trifluoromethyl)cyclopent-3-enecarboxylic Acid Derivatives: Platforms for Bifunctional Cyclic Trifluoromethyl Building Blocks
  作者：Fabienne Grellepois、Vincent Kikelj、Nicolas Coia、Charles Portella

  DOI：10.1002/ejoc.201101321

  日期：2012.1

  applications of 1-(trifluoromethyl)cyclopent-3-ene-1-carboxylic acid and itsesters, promising new trifluoromethylated cyclic building blocks. Initially prepared starting from a pentafluorodithiopropanoic ester, a more convenient and effective approach has been developed starting from commercially available trifluoropropanoic acid or its methyl ester. The interest in these building blocks is exemplified

  我们在此报告了 1-（三氟甲基）环戊-3-烯-1-羧酸及其酯的合成和应用，有望成为新的三氟甲基化环状结构单元。最初从五氟二硫代丙酸酯开始制备，从市售的三氟丙酸或其甲酯开始开发了一种更方便和有效的方法。对这些构件的兴趣体现在它们用作各种双官能三氟甲基环戊烷衍生物的平台。
• Enantioselective Desymmetrization via Carbonyl-Directed Catalytic Asymmetric Hydroboration and Suzuki–Miyaura Cross-Coupling
  作者：Gia L. Hoang、Zhao-Di Yang、Sean M. Smith、Rhitankar Pal、Judy L. Miska、Damaris E. Pérez、Libbie S. W. Pelter、Xiao Cheng Zeng、James M. Takacs

  DOI：10.1021/ol503764d

  日期：2015.2.20

  The rhodium-catalyzed enantioselective desymmetrization of symmetric gamma,delta-unsaturated amides via carbonyl-directed catalytic asymmetric hydroboration (directed CAHB) affords chiral secondary organoboronates with up to 98% ee. The chiral gamma-borylated products undergo palladium-catalyzed Suzuki-Miyaura cross-coupling via the trifluoroborate salt with stereoretention.