2-Naphthalenol, 1-[(S)-phenyl[(E)-(phenylmethylene)amino]methyl] | 219897-41-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-Naphthalenol, 1-[(S)-phenyl[(E)-(phenylmethylene)amino]methyl]
• 英文别名: 1-[(S)-(benzylideneamino)-phenylmethyl]naphthalen-2-ol
• CAS: 219897-41-3
• 化学式: C₂₄H₁₉NO
• 分子量: 337.421
• InChiKey: IBKFPODMQLEYRC-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Naphthalenol, 1-[(S)-phenyl[(E)-(phenylmethylene)amino]methyl] 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲苯 为溶剂， 以89%的产率得到1-((S)-phenyl(phenylmethylamino)methyl)naphthalen-2-ol
  参考文献：
  名称：

  Development of chiral heteroleptic magnesium amides; asymmetric deprotonations mediated by six-membered metallocyclic amidomagnesium naphtholates

  摘要：

  A series of enantioenriched six-membered metallocyclic amidomagnesium naphtholates were prepared and used to probe the structure-reactivity/selectivity relationships of heteroleptic magnesium base complexes within asymmetric deprotonation reactions. An effective complex was identified and applied within enantioselective enolisation processes, delivering good levels of enantioselectivity and also revealing key structural requirements for achieving such selectivity. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.06.052
• 作为产物：
  描述：

  苯甲醛 在 L-酒石酸 、 氨 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 8.75h， 生成 2-Naphthalenol, 1-[(S)-phenyl[(E)-(phenylmethylene)amino]methyl]
  参考文献：
  名称：

  Development of chiral heteroleptic magnesium amides; asymmetric deprotonations mediated by six-membered metallocyclic amidomagnesium naphtholates

  摘要：

  A series of enantioenriched six-membered metallocyclic amidomagnesium naphtholates were prepared and used to probe the structure-reactivity/selectivity relationships of heteroleptic magnesium base complexes within asymmetric deprotonation reactions. An effective complex was identified and applied within enantioselective enolisation processes, delivering good levels of enantioselectivity and also revealing key structural requirements for achieving such selectivity. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.06.052

文献信息

• 1-(α-Aminobenzyl)-2-naphthol: A New Chiral Auxiliary for the Synthesis of Enantiopure α-Aminophosphonic Acids
  作者：Kirill E. Metlushka、Boris A. Kashemirov、Viktor F. Zheltukhin、Dilyara N. Sadkova、Bernd Büchner、Christian Hess、Olga N. Kataeva、Charles E. McKenna、Vladimir A. Alfonsov

  DOI：10.1002/chem.200802540

  日期：2009.7.6

  Ooh Betti! A new diastereoselective synthesis of α‐aminophosphonates has been developed based on the reaction of trialkyl phosphites with chiral imines derived from (R)‐ or (S)‐1‐(α‐aminobenzyl)‐2‐naphthol (Betti base; see scheme, X=H, CH3, or Br). The reaction proceeds with high diastereoselectivity. Treatment with HCl results in the formation of the desired α‐aminophosphonic acids.

  哦，贝蒂！基于亚磷酸三烷基酯与衍生自（R）-或（S）-1-（α-氨基苄基）-2-萘酚的手性亚胺的反应，开发了一种新的非对映选择性的α-氨基膦酸酯合成（贝蒂碱;参见图式， X = H，CH 3或Br）。反应以高非对映选择性进行。用HCl处理可形成所需的α-氨基膦酸。