(1S,2S)-2-ethyl-1,2-dihydronaphthalen-1-ol | 669078-42-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1S,2S)-2-ethyl-1,2-dihydronaphthalen-1-ol
• 英文别名: (1S,2S)-2-ethyl-1,2-dihydronaphth-1-ol；(+)-2-ethyl-1,2-dihydronaphth-1-ol；2-ethyl-1,2-dihydronaphthalen-1-ol；1-Naphthalenol, 2-ethyl-1,2-dihydro-, (1S,2S)-
• CAS: 669078-42-6
• 化学式: C₁₂H₁₄O
• 分子量: 174.243
• InChiKey: SFQYQPZTIRBWIC-CABZTGNLSA-N

物化性质

• 沸点：
  310.0±11.0 °C(Predicted)
• 密度：
  1.061±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1,4-二氢-1,4-环氧萘 、 diethylzinc 在 PdCl₂(cod)2 (R,R)-2,3-bis((1-adamantyl)methylphosphino)quinoxaline 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (1S,2S)-2-ethyl-1,2-dihydronaphthalen-1-ol
  参考文献：
  名称：

  具有（1-金刚烷基）甲基膦基的空气稳定 P-手性双齿膦配体

  摘要：

  空气稳定的二膦配体，(R,R)-2,3-双((1-金刚烷基)-甲基膦基)喹喔啉，是通过对映体纯的 (S)-(1-金刚烷基)甲基膦-硼烷与 2 ,3-二氯喹喔啉。该配体在Rh催化的不对称氢化和Pd催化的不对称开环反应中表现出优异的对映选择性。

  DOI：

  10.1246/cl.2007.500

文献信息

• Fesulphos-Palladium(II) Complexes as Well-Defined Catalysts for Enantioselective Ring Opening of Meso Heterobicyclic Alkenes with Organozinc Reagents
  作者：Silvia Cabrera、Ramón Gómez Arrayás、Inés Alonso、Juan C. Carretero

  DOI：10.1021/ja055692b

  日期：2005.12.1

  The air-stable and readily available cationic methyl palladium(II) complexes of planar chiral Fesulphos ligands [(Fesulphos)Pd(Me)(PhCN)]+ X- are highly efficient catalysts for the alkylative ring opening of oxa- and azabicyclic alkenes with dialkylzinc reagents, showing broad scope with regards to both the bicyclic substrate and the dialkylzinc reagent. Catalyst loading as low as 0.5 mol % is sufficient

  空气稳定且易于获得的平面手性 Fesulphos 配体 [(Fesulphos)Pd(Me)(PhCN)]+ X- 的阳离子甲基钯 (II) 配合物是用于氧杂和氮杂双环烯烃烷基化开环的高效催化剂二烷基锌试剂，在双环底物和二烷基锌试剂方面显示出广泛的范围。在大多数情况下，低至 0.5 mol% 的催化剂负载量足以实现良好的产率和对映选择性范围为 94 --> 99% ee。Fesulphos = (1-phosphino-2-sulfenylferrocene); X- = 四[3,5-双(三氟甲基)苯基]硼酸盐或PF6(-)]。}结合计算计算和X射线结构分析的机械研究已经合理化了高不对称感应的起源。
• 2, 3-Bis(dialkylphosphino)pyrazine derivative, process of producing the same, and metal complex having the same as ligand
  申请人：Imamoto Tsuneo

  公开号：US20070021610A1

  公开（公告）日：2007-01-25

  An optically active 2,3-bis(dialkylphosphino)pyrazine derivative represented by formula (1) is disclosed. The pyrazine derivative is preferably a quinoxaline derivative represented by formula (2). In formula (1) and (2), R 1 is preferably a t-butyl or adamantyl group, and R 2 is preferably a methyl group. wherein R 1 is a substituted or unsubstituted, straight chain or branched alkyl group having 2 to 10 carbon atoms; R 2 is a substituted or unsubstituted, straight chain or branched alkyl group having fewer carbon atoms than R 1 ; and R 3 and R 4 , which may be the same or different, are each a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, or R 3 and R 4 are taken together to form a saturated or unsaturated ring. wherein R 1 and R 2 are as defined above; and R 5 is a monovalent substituent.

  公开了一种由式（1）表示的光学活性的2,3-双(二烷基膦基)吡嗪衍生物。该吡嗪衍生物最好是由式（2）表示的喹啉衍生物。在式（1）和（2）中，R1最好是叔丁基或金刚烷基，R2最好是甲基。 其中，R1是取代或未取代的，具有2至10个碳原子的直链或支链烷基基团；R2是取代或未取代的，碳原子比R1少的直链或支链烷基基团；R3和R4，可以相同也可以不同，分别是氢原子或具有1至6个碳原子的烷基基团，或者R3和R4一起形成饱和或不饱和环。 其中，R1和R2如上所定义；R5是一价取代基。
• Nickel-catalyzed <i>syn</i>-stereocontrolled ring-opening of oxa- and azabicyclic alkenes with dialkylzinc reagents
  作者：Yingying Deng、Wen Yang、Yongqi Yao、Xin Yang、Xiongjun Zuo、Dingqiao Yang

  DOI：10.1039/c8ob02864h

  日期：——

  A new nickel-catalyzed syn-stereocontrolled ring-opening of oxa- and azabicyclic alkenes with dialkylzinc reagents was developed, which afforded the corresponding cis-2-alkyl-1,2-dihydronaphthalen-1-ols and 1,2-alkyl amide derivatives in moderate to excellent yields (up to 99% yield) under mild conditions. In this work, we successfully avoided obtaining hydride addition byproducts arising from β-hydride

  用二烷基锌试剂开发了一种新的镍催化的氧杂-和氮杂双环烯烃的顺式立体控制开环反应，得到相应的顺式-2-烷基-1,2-二氢萘-1-醇和1,2-烷基酰胺衍生物在温和的条件下，以中等至优异的产量（高达99％的产量）。在这项工作中，我们成功地避免了由于在乙基镍物质上消除β-氢化物而产生的氢化物加成副产物。此外，还提出了一种可能的开环反应机理。
• Scope of Palladium-Catalyzed Alkylative Ring Opening
  作者：Mark Lautens、Sheldon Hiebert

  DOI：10.1021/ja037550s

  日期：2004.2.1

  We have explored the scope of the palladium-catalyzed nucleophilic ring opening methodology. New highly selective and highly active catalysts have been found for the ring opening of oxabenzonorbornadienes. Employing these catalysts, the addition of various alkyl nucleophiles to oxabenzonorbornadiene has been achieved. In addition, reaction of diethylzinc with [3.2.1] oxabicyclic alkenes has been accomplished

  我们探索了钯催化亲核开环方法的范围。已发现用于氧杂苯并降冰片二烯开环的新型高选择性和高活性催化剂。使用这些催化剂，已经实现了将各种烷基亲核试剂添加到氧杂苯并降冰片二烯中。此外，已完成二乙基锌与 [3.2.1] 氧杂双环烯烃的反应，以产生开环产物以及官能化的烯烃加成产物。
• Optically-active bis(alkynylphosphino) ethane-borane derivative and process for producing the same
  申请人：Imamoto Tsuneo

  公开号：US20080221362A1

  公开（公告）日：2008-09-11

  An optically-active bis(alkynylphosphino)ethane-borane derivative represented by formula (1): wherein R 1 and R 2 , which may be the same or different, each represent an alkyl group, a phenyl group, an alkylsilyl group or a hydrogen atom; R 3 represents a branched alkyl group, an alicyclic hydrocarbon group or an aromatic hydrocarbon group; and the asterisk * indicates an optically-active site. The derivative (1) is prepared by bromination of, e.g., an (S)-t-butylmethylphosphine-borane, reaction with an alkynyl lithium, deprotonation, followed by oxidative coupling. Deprotection of the derivative (1) by deboranation gives an optically-active bis(alkynylphosphino)ethane derivative useful as a ligand providing an asymmetric catalyst for catalytic asymmetric synthesis. The asymmetric catalyst having the ligand exhibits high selectivity and catalyst activity.

  公式（1）表示的具有光学活性的双(炔基膦)乙烷硼衍生物： 其中R1和R2，可以相同也可以不同，分别代表一个烷基基团、苯基、烷基硅基团或氢原子；R3代表一个支链烷基基团、脂环烃基团或芳香烃基团；星号*表示一个光学活性位点。 通过溴化，例如(S)-叔丁基甲基膦硼烷，与炔基锂反应，去质子化，然后进行氧化偶联制备衍生物（1）。通过去硼烷解保护衍生物（1），得到一种有用的作为提供不对称催化剂的光学活性双(炔基膦)乙烷衍生物，该催化剂具有高选择性和催化活性。