4,4-bis(benzyloxymethyl)-1-methyl-2-methylenecyclopentanecarbaldehyde | 1011266-14-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 4,4-bis(benzyloxymethyl)-1-methyl-2-methylenecyclopentanecarbaldehyde
• 英文别名: 1-Methyl-2-methylidene-4,4-bis(phenylmethoxymethyl)cyclopentane-1-carbaldehyde
• CAS: 1011266-14-0
• 化学式: C₂₄H₂₈O₃
• 分子量: 364.485
• InChiKey: LTDUZDWDHIGSBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4,4-bis(benzyloxymethyl)-2-methylhept-6-ynal 在 copper(II) bis(trifluoromethanesulfonate) 、 环己胺 、 三苯基膦 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 16.0h， 以95%的产率得到4,4-bis(benzyloxymethyl)-1-methyl-2-methylenecyclopentanecarbaldehyde
  参考文献：
  名称：

  铜(I)和伯胺协同催化的甲酰基炔烃的室温碳环化

  摘要：

  描述了一种有效的 CuI/胺催化系统，用于室温下 α-二取代甲炔的碳环化。将氨基催化与铜（I）催化的炔烃活化相结合，可以在温和条件下实现多种功能化底物的清洁碳环化。这种新型协同催化系统允许形成各种碳环和杂环，包括吡咯烷，收率良好。还讨论了该过程的机械方面。

  DOI：

  10.1002/ejoc.201100464

文献信息

• Copper(i)–amine metallo-organocatalyzed synthesis of carbo- and heterocyclic systems
  作者：Benjamin Montaignac、Victor Östlund、Maxime R. Vitale、Virgnie Ratovelomanana-Vidal、Véronique Michelet

  DOI：10.1039/c2ob06449a

  日期：——

  and atom economical synthesis of 5-membered cyclic structures has been achieved through the combination of amino catalysis and metal catalysis. The discovery of a novel metallo-organocatalytic system merging the use of a catalytic copper(I) complex and a catalytic amount of cyclohexylamine allowed the room temperature preparation of a broad range of skeletons such as cyclopentanes, indanes, pyrrolidines

  通过氨基催化和金属催化的结合，实现了五元环状结构的高效，原子经济的合成。结合催化铜（I）配合物和催化量的铜（I）的新型金属-有机催化体系的发现。环己胺 可以在室温下制备各种骨架，例如环戊烷，茚满，吡咯烷和 四氢呋喃，是许多生物学相关分子的重要结构核心。提出了力学研究。
• Combined InCl₃- and Amine-Catalyzed Intramolecular Addition of α-Disubstituted Aldehydes onto Unactivated Alkynes
  作者：Benjamin Montaignac、Maxime R. Vitale、Veronique Michelet、Virginie Ratovelomanana-Vidal

  DOI：10.1021/ol100729t

  日期：2010.6.4

  The combination of enamine-type catalysis to the indium-catalyzed activation of alkynes allows the efficient preparation of functionalized cyclopentanes bearing a quaternary stereogenic center. A broad range of formylalkynyl derivatives has been prepared. The InCl3/(Cy)(i-Pr)NH system efficiently promotes the carbocyclization reaction of alpha-disubstituted aldehydes in good to excellent yields.
• InCl₃/CyNH₂ Cocatalyzed Carbocyclization Reaction: An Entry to α-Disubstituted <i>exo</i>-Methylene Cyclopentanes
  作者：Benjamin Montaignac、Maxime R. Vitale、Virginie Ratovelomanana-Vidal、Véronique Michelet

  DOI：10.1021/jo1018552

  日期：2010.12.3

  An efficient and cheap synthetic approach to functionalized exo-methylene cyclopentanes has been developed from alpha-disubstituted formyl-alkynes by merging amine catalysis with the indium activation of alkynes. We uncovered the crucial role of the amine cocatalyst and the development of a new cooperative catalytic system allowed the cyclization of a broad range of substrates. A mechanistic study was realized in order to rationalize the determining influence of the amine cocatalyst.
• Direct Carbocyclization of Aldehydes with Alkynes:  Combining Gold Catalysis with Aminocatalysis
  作者：Jörg T. Binder、Benedikt Crone、Timm T. Haug、Helge Menz、Stefan F. Kirsch

  DOI：10.1021/ol800092p

  日期：2008.3.1

  A combination of gold(l) complexes and amine bases catalyzes the 5-exo-dig cyclization of formyl alkynes. This direct alpha-functionalization of aldehydes with unactivated alkynes does not involve the use of preformed enol equivalents.