[1-(3-Formyl-2-hydroxynaphthalen-1-yl)naphthalen-2-yl] 2,2-dimethylpropanoate | 345659-35-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: [1-(3-Formyl-2-hydroxynaphthalen-1-yl)naphthalen-2-yl] 2,2-dimethylpropanoate
• 英文别名: [1-(3-formyl-2-hydroxynaphthalen-1-yl)naphthalen-2-yl] 2,2-dimethylpropanoate
• CAS: 345659-35-0；874280-74-7
• 化学式: C₂₆H₂₂O₄
• 分子量: 398.458
• InChiKey: UOXWWTKHNIBKSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[(1R,2R)-2-氨基环己基]-N'-[3,5-双(三氟甲基)苯基]硫脲 、 [1-(3-Formyl-2-hydroxynaphthalen-1-yl)naphthalen-2-yl] 2,2-dimethylpropanoate 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以65%的产率得到(R)-3'-(((1R,2R)-2-(3-(3,5-bis(trifluoromethyl)phenyl)thioureido)cyclohexyl-amino)methyl)-2'-hydroxy-1,1'-binaphthyl-2-yl pivalate
  参考文献：
  名称：

  Enantioselective Organocatalytic Three-Component Petasis Reaction among Salicylaldehydes, Amines, and Organoboronic Acids

  摘要：

  The catalytic enantioselective three-component Petasis reaction among salicylaldehydes, amines, and organoboronic acids with a newly designed thiourea-binol catalyst is presented. A broad range of alkylaminophenols can be obtained in good yield (up to 92%) and good to high enantioselectivity (up to 95% ee). A possible reaction pathway for this catalytic enantioselective Petasis reaction is tentatively proposed.

  DOI：

  10.1021/ol203109a
• 作为产物：
  描述：

  rac-2,2'-bis-(methoxymethoxy)-1,1'-binaphthalene 在 盐酸 、 叔丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 2.0h， 生成 [1-(3-Formyl-2-hydroxynaphthalen-1-yl)naphthalen-2-yl] 2,2-dimethylpropanoate
  参考文献：
  名称：

  新的空间位阻Salen-Mn（III）配合物催化的烯烃的对映选择性环氧化

  摘要：

  由BINOL衍生的醛制备了新的位阻手性Salen-Mn（III）配合物5和6。这些物质催化烯烃的高效，对映选择性NaOCl促进的环氧化，在顺式-β-甲基苯乙烯和2,2-二甲基亚甲基的环氧化中观察到高达96-99％ee的对映选择性。

  DOI：

  10.1016/s0040-4039(01)00195-2

文献信息

• Synthesis of sterically controlled chiral β-amino alcohols and their application to the catalytic asymmetric sulfoxidation of sulfides
  作者：Yong-Chul Jeong、Yao Dong Huang、Soojin Choi、Kwang-Hyun Ahn

  DOI：10.1016/j.tetasy.2005.07.035

  日期：2005.10

  enantiomerically pure aziridine-2-carboxylic acid menthol ester 13. Vanadium complexes of the chiral Schiff-base ligands prepared from the β-amino alcohols catalyze an efficient enantioselective sulfoxidation of alkyl aryl sulfides, while enantioselectivities as high as 96% ee can be observed in the sulfoxidation of benzyl aryl sulfides.

  由对映体纯的氮丙啶-2-羧酸薄荷醇酯13制备立体受阻和对映体纯的β-氨基醇8a和8b。由β-氨基醇制得的手性席夫碱配体的钒配合物催化烷基芳基硫醚的有效对映选择性硫氧化，而在苄基芳基硫醚的硫氧化中可观察到高达96％ee的对映选择性。
• Enantioselective oxidation of sulfides with hydrogen peroxide catalyzed by vanadium complex of sterically hindered chiral Schiff bases
  作者：Yong-Chul Jeong、Soojin Choi、Yao Dong Hwang、Kwang-Hyun Ahn

  DOI：10.1016/j.tetlet.2004.10.070

  日期：2004.12

  Sterically hindered chiral Schiff base ligands 4a–d were prepared from an aldehyde derived from BINOL. The vanadium complexes of the ligands catalyze an efficient, enantioselective H2O2-promoted sulfoxidation of alkyl aryl sulfides, and enantioselectivities as high as 98–99% ee are observed in the sulfoxidation of benzyl aryl sulfides.

  由BINOL衍生的醛制备了位阻手性席夫碱配体4a – d。配体的钒配合物催化烷基芳基硫醚的高效，对映选择性H 2 O 2促进的硫氧化，在苄基芳基硫醚的硫氧化中观察到高达98-99％ee的对映选择性。
• Enantioselective Organocatalytic Three-Component Petasis Reaction among Salicylaldehydes, Amines, and Organoboronic Acids
  作者：Wen-Yong Han、Zhi-Jun Wu、Xiao-Mei Zhang、Wei-Cheng Yuan

  DOI：10.1021/ol203109a

  日期：2012.2.17

  The catalytic enantioselective three-component Petasis reaction among salicylaldehydes, amines, and organoboronic acids with a newly designed thiourea-binol catalyst is presented. A broad range of alkylaminophenols can be obtained in good yield (up to 92%) and good to high enantioselectivity (up to 95% ee). A possible reaction pathway for this catalytic enantioselective Petasis reaction is tentatively proposed.
• Enantioselective epoxidation of olefins catalyzed by new sterically hindered salen–Mn(III) complexes
  作者：Kwang-Hyun Ahn、Sang Wook Park、Soojin Choi、Hyun-Ju Kim、Chi Jang Moon

  DOI：10.1016/s0040-4039(01)00195-2

  日期：2001.3

  New, sterically hindered chiral salen–Mn(III) complexes, 5 and 6, were prepared from an aldehyde derived from BINOL. These substances catalyze efficient, enantioselective NaOCl-promoted epoxidations of olefins and enantioselectivities as high as 96–99% ee are observed in epoxidations of cis-β-methylstyrene and 2,2-dimethylchromene.

  由BINOL衍生的醛制备了新的位阻手性Salen-Mn（III）配合物5和6。这些物质催化烯烃的高效，对映选择性NaOCl促进的环氧化，在顺式-β-甲基苯乙烯和2,2-二甲基亚甲基的环氧化中观察到高达96-99％ee的对映选择性。