2-((1R,5R)-3,5-diphenylcyclopent-2-en-1-yl)furan

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-((1R,5R)-3,5-diphenylcyclopent-2-en-1-yl)furan
• 英文别名: 2-((1R,5R)-3,5-Diphenylcyclopent-2-en-1-yl)furan；2-[(1R,5R)-3,5-diphenylcyclopent-2-en-1-yl]furan
• 化学式: C₂₁H₁₈O
• 分子量: 286.373
• InChiKey: KLYAYQOBJGAWRL-VQTJNVASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  反式-查耳酮 、 反-3-(2-呋喃基)丙烯醛 在 1,3-bis(methylsulfonyl)-1H-imidazol-3-ium chloride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 以85%的产率得到2-((1R,5R)-3,5-diphenylcyclopent-2-en-1-yl)furan
  参考文献：
  名称：

  N-杂环卡宾/路易斯酸协同催化与均烯醇的高立体选择性环化反应

  摘要：

  一种利用 N-杂环卡宾/路易斯酸协同催化的新方法可以从具有高水平非对映选择性和对映选择性的烯醛和查尔酮衍生物中获得顺式 1,3,4-三取代的环戊烯。Ti(OiPr)(4) 作为路易斯酸的存在允许有效的底物预组织，这转化为高水平的非对映选择性。此外，我们证明了通过使用催化量的手性路易斯酸作为光学活性促进剂的独特来源来控制 NHC 催化反应的绝对立体化学的可能性。

  DOI：

  10.1021/ja910666n

文献信息

• NHC-catalyzed reactions of enals with water as a solvent
  作者：Wendy Wen Yi Leong、Xingkuan Chen、Yonggui Robin Chi

  DOI：10.1039/c3gc40397a

  日期：——

  Water is demonstrated as a suitable solvent for NHC-catalyzed reactions of enals. The use of D2O as a solvent allows for the effective incorporation of deuterium isotopes into organic molecules.

  水被证明是适合用于NHC催化的烯醛反应的溶剂。使用D2O作为溶剂能有效地将氘同位素引入有机分子中。
• β-Carbon activation of saturated carboxylic esters through N-heterocyclic carbene organocatalysis
  作者：Zhenqian Fu、Jianfeng Xu、Tingshun Zhu、Wendy Wen Yi Leong、Yonggui Robin Chi

  DOI：10.1038/nchem.1710

  日期：2013.10

  The activation of the α-carbons of carboxylic esters and related carbonyl compounds to generate enolate equivalents as nucleophiles is one of the most powerful strategies in organic synthesis. We reasoned that the horizons of chemical synthesis could be greatly expanded if the typically inert β-carbons of saturated esters could be used as nucleophiles. However, despite the rather significant fundamental

  活化羧酸酯和相关羰基化合物的 α-碳以生成烯醇等价物作为亲核试剂是有机合成中最有效的策略之一。我们推断，如果饱和酯的典型惰性 β-碳可以用作亲核试剂，则化学合成的范围可以大大扩展。然而，尽管具有相当重要的基本和实用价值，但直接使用饱和羰基化合物的 β-碳作为亲核试剂仍然难以捉摸。在这里，我们报告了使用N催化活化作为亲核试剂的简单饱和酯 β-碳（β-碳活化）-杂环卡宾有机催化剂。催化产生的亲核β-碳与亲电子试剂如烯酮和亚胺发生对映选择性反应。鉴于已证明酯 α-碳具有丰富的化学性质，我们预计这种饱和酯 β-碳的催化活化模式将为新的有用反应和合成策略开辟一个有价值的新领域。
• [EN] ACTIVATION OF CARBONYL &bgr;-CARBONS FOR CHEMICAL TRANSFORMATIONS<br/>[FR] ACTIVATION DE &Bgr;-CARBONES DE CARBONYLE POUR DES TRANSFORMATIONS CHIMIQUES
  申请人：UNIV NANYANG TECH

  公开号：WO2014142755A1

  公开（公告）日：2014-09-18

  The present invention relates to a method for synthesizing a compound of Formula (I) as defined herein, comprising: (i) activating a compound of Formula (II) as defined herein, by reacting said compound of Formula (II) with a compound of Formula (III) as defined herein, in the presence of a base, to obtain a compound of Formula (IV) as defined herein; and (ii) reacting the compound of Formula (IV) with an electrophile to obtain the compound of Formula (I). The present invention further relates to the organocatalysts used in the described methods and their respective uses.

  本发明涉及一种合成式(I)化合物的方法，包括：(i) 通过在碱的存在下，将式(II)化合物与式(III)化合物反应，激活式(II)化合物，以得到式(IV)化合物；以及(ii) 通过将式(IV)化合物与亲电试剂反应，得到式(I)化合物。本发明还涉及所述方法中使用的有机催化剂及其相应的用途。
• Activation of carbonyl beta-carbons for chemical transformations
  申请人：Nanyang Technological University

  公开号：US11306097B2

  公开（公告）日：2022-04-19

  The present invention relates to a method for synthesizing a compound of Formula (I) as defined herein, comprising: (i) activating a compound of Formula (II) as defined herein, by reacting said compound of Formula (II) with a compound of Formula (III) as defined herein, in the presence of a base, to obtain a compound of Formula (IV) as defined herein; and (ii) reacting the compound of Formula (IV) with an electrophile to obtain the compound of Formula (I). The present invention further relates to the organocatalysts used in the described methods and their respective uses.

  本发明涉及一种合成式（I）化合物的方法 的方法，包括： (i) 活化式（II）化合物 将所述式 (II) 化合物与式 (III) 化合物反应，得到如本文所定义的化合物 如本文所定义，在碱存在下，得到式（IV）化合物 如本文所定义；以及(ii)使式(IV)化合物与亲电子体反应，得到式(I)化合物。本发明进一步涉及所述方法中使用的有机催化剂及其各自的用途。
• ACTIVATION OF CARBONYL BETA-CARBONS FOR CHEMICAL TRANSFORMATIONS
  申请人：Nanyang Technological University

  公开号：US20160039827A1

  公开（公告）日：2016-02-11

  The present invention relates to a method for synthesizing a compound of Formula (I) as defined herein, comprising: (i) activating a compound of Formula (II) as defined herein, by reacting said compound of Formula (II) with a compound of Formula (III) as defined herein, in the presence of a base, to obtain a compound of Formula (IV) as defined herein; and (ii) reacting the compound of Formula (IV) with an electrophile to obtain the compound of Formula (I). The present invention further relates to the organocatalysts used in the described methods and their respective uses.