2-(2-(naphthalen-2-yl)-2-oxoethoxy)benzaldehyde | 1013938-57-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(2-(naphthalen-2-yl)-2-oxoethoxy)benzaldehyde
• 英文别名: 2-(2-Naphthalen-2-yl-2-oxoethoxy)benzaldehyde；2-(2-naphthalen-2-yl-2-oxoethoxy)benzaldehyde
• CAS: 1013938-57-2
• 化学式: C₁₉H₁₄O₃
• 分子量: 290.318
• InChiKey: KOQFOUIHVBFPEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 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：

  2-(2-(naphthalen-2-yl)-2-oxoethoxy)benzaldehyde 在 (5aR,6R,9S,9aS)-6,11,11-trimethyl-2-(2,4,6-trichlorophenyl)-5a,6,7,8,9,9a-hexahydro-4H-6,9-methanobenzo[b][1,2,4]-triazolo[4,3-d][1,4]oxazin-2-ium tetraphenylborate 、 2-叔丁基亚氨基-2-二乙基氨基-1,3-二甲基全氢-1,3,2-二氮杂磷 作用下， 反应 1.0h， 以99%的产率得到(S)-3-hydroxy-3-(naphthalen-2-yl)chroman-4-one
  参考文献：
  名称：

  Enantioselective Synthesis of Chromanones Bearing Quaternary Substituted Stereocenters Catalyzed by (1R)-Camphor-Derived N-Heterocyclic Carbenes

  摘要：

  A catalytic asymmetric intramolecular crossed-benzoin reaction for the synthesis of chromanones by novel camphor-derived N-heterocyclic carbenes is described. The corresponding chromanones bearing quaternary stereogenic centers were isolated in high yields with high to excellent enantioselectivity.

  DOI：

  10.1021/acs.joc.5b01029
• 作为产物：
  描述：

  2-[2-(1,3-dithian-2-yl)phenoxy]-1-(naphthalen-2-yl)-ethanone 在 mercury(II) trifluoroacetate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以92%的产率得到2-(2-(naphthalen-2-yl)-2-oxoethoxy)benzaldehyde
  参考文献：
  名称：

  Enantioselective Synthesis of Chromanones Bearing Quaternary Substituted Stereocenters Catalyzed by (1R)-Camphor-Derived N-Heterocyclic Carbenes

  摘要：

  A catalytic asymmetric intramolecular crossed-benzoin reaction for the synthesis of chromanones by novel camphor-derived N-heterocyclic carbenes is described. The corresponding chromanones bearing quaternary stereogenic centers were isolated in high yields with high to excellent enantioselectivity.

  DOI：

  10.1021/acs.joc.5b01029

文献信息

• Rh-Catalyzed Carbonyl Hydroacylation:  An Enantioselective Approach to Lactones
  作者：Zengming Shen、Hasan A. Khan、Vy M. Dong

  DOI：10.1021/ja7109025

  日期：2008.3.1

  This communication describes the design and execution of a novel approach to forming chiral lactones via C−H bond activation. The strategy features an unprecedented enantioselective Rh-catalyzed hydroacylation of carbon−oxygen double bonds. Representative keto-aldehydes (derived from salicylaldehyde) undergo cyclization with complete regioselectivity to afford seven-membered lactones in great enantiomeric

  该通讯描述了一种通过 CH 键活化形成手性内酯的新方法的设计和执行。该策略的特点是前所未有的对映选择性 Rh 催化的碳氧双键加氢酰化。代表性的酮醛（衍生自水杨醛）以完全区域选择性进行环化，以提供对映体过量（≥99% ee）的七元内酯。膦配体的碱性显示出在促进加氢酰化而不是竞争性脱羰中起关键作用。
• Copper-Catalyzed Intramolecular Aldehyde–Ketone Nucleophilic Additions for the Synthesis of Chromans Bearing a Tertiary Alcohol Motif
  作者：Chenghao Zhu、Wenbo Jiang、Da Ma

  DOI：10.1021/acs.joc.3c02365

  日期：2024.1.19

  The synthesis of chroman-3-ol derivatives via intramolecular nucleophilic additions has been established. Aldehydes can be used as alkyl carbanion equivalents via reductive polarity reversal which is facilitated by a copper catalyst and N-heterocyclic carbene ligand under mild conditions. The key to success is the difference in reaction activity between aldehydes and ketones. Finally, this methodology

  已经建立了通过分子内亲核加成合成色满-3-醇衍生物的方法。通过铜催化剂和 N-杂环卡宾配体在温和条件下促进还原极性反转，醛可用作烷基碳负离子等价物。成功的关键是醛和酮之间反应活性的差异。最后，该方法还可用于构建含有叔醇的其他环状结构，包括四氢化萘、环己烷、茚满和9,10-二氢菲。
• Shen, Zengming; Dornan, Peter K.; Khan, Hasan A., Journal of the American Chemical Society, 2009, vol. 131, p. 1077 - 1091
  作者：Shen, Zengming、Dornan, Peter K.、Khan, Hasan A.、Woo, Tom K.、Dong, Vy M.

  DOI：——

  日期：——
• Enantioselective Synthesis of Chromanones Bearing Quaternary Substituted Stereocenters Catalyzed by (1<i>R</i>)-Camphor-Derived <i>N</i>-Heterocyclic Carbenes
  作者：Zbigniew Rafiński、Anna Kozakiewicz

  DOI：10.1021/acs.joc.5b01029

  日期：2015.8.7

  A catalytic asymmetric intramolecular crossed-benzoin reaction for the synthesis of chromanones by novel camphor-derived N-heterocyclic carbenes is described. The corresponding chromanones bearing quaternary stereogenic centers were isolated in high yields with high to excellent enantioselectivity.