N,N-Diethyl-2-formyl-1-naphthamide | 246517-34-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N,N-Diethyl-2-formyl-1-naphthamide
• 英文别名: N,N-diethyl-2-formylnaphthalene-1-carboxamide
• CAS: 246517-34-0
• 化学式: C₁₆H₁₇NO₂
• 分子量: 255.316
• InChiKey: DLAKCKRHCYVNPT-UHFFFAOYSA-N

物化性质

• 沸点：
  459.3±28.0 °C(Predicted)
• 密度：
  1.142±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N-Diethyl-2-formyl-1-naphthamide 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 1.67h， 以87%的产率得到2-Hydroxymethyl-naphthalene-1-carboxylic acid diethylamide
  参考文献：
  名称：

  使用脯氨酸衍生的咪唑啉和麻黄碱衍生的恶唑烷类化合物动态拆分阻转异构酰胺

  摘要：

  阻转异构的叔2-甲酰基萘酰胺或2-甲酰基苯甲酰胺与一些手性二胺和氨基醇的缩合通过动态拆分过程导致带有手性咪唑烷或恶唑烷的叔酰胺的单一阻转异构体。新杂环的水解与起始醛的动态热力学拆分竞争，并且快速还原可分离出对映异构体富集形式的带有2-羟甲基取代基的阻转异构酰胺。提供了反应在热力学控制下的证据。

  DOI：

  10.1016/j.tet.2004.01.101
• 作为产物：
  描述：

  2-((3R,7aS)-2-Phenyl-hexahydro-pyrrolo[1,2-c]imidazol-3-yl)-naphthalene-1-carboxylic acid diethylamide 在 盐酸 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 N,N-Diethyl-2-formyl-1-naphthamide
  参考文献：
  名称：

  Enantioselective Synthesis of Atropisomeric Amides by Dynamic Resolution: Thermodynamic Control with a Proline-Derived Diamine Resolving Agent

  摘要：

  By exploiting the thermal instability about the Ar-CO axis at high temperature, atropisomeric amides can be dynamically resolved to provide material with up to 96.5 % ee in 70-80 % overall yield from racemic starting material. The amides are coupled with a diamine resolving agent and equilibrated to single diastereoisomers. Hydrolysis returns enantiomerically enriched amide (see reaction scheme).

  DOI：

  10.1002/(sici)1521-3773(19990903)38:17<2556::aid-anie2556>3.0.co;2-q

文献信息

• Atroposelective attack of nucleophiles on 2-formyl-1-naphthamides and their derivatives: chelation and non-chelation control
  作者：Jonathan Clayden、Catherine McCarthy、Neil Westlund、Christopher S. Frampton

  DOI：10.1039/b000669f

  日期：——

  Organometallic nucleophiles attack 2-formyl-1-naphthamides to give secondary alcohols with widely varying atroposelectivity. By careful choice of reagent, selectivities of up to >99∶1 in favour of either the anti or the syn atropisomer can be obtained. Ethers and amines may be synthesised atroposelectively from acetals or imines. The sense of the selectivity is determined by the reactive conformation of the Ar–CHO bond, itself dependent on the coordinating and chelating ability of the nucleophile’s counterion. The roles of conformation, Lewis acids, and chelation/non-chelation control in relation to stereoselectivity are discussed.

  有机金属核苷类物质攻击2-芳醛-1-萘酰胺，生成具有广泛变异的次级醇的非对映选择性。通过仔细选择试剂，可以获得高达99:1的选择性，偏向于反式或顺式对映异构体。醚类和胺类可以从缩醛或亚胺中选择性合成。选择性的方向由Ar–CHO键的反应构象决定，而这又依赖于核苷的配对离子的配位和螯合能力。文中讨论了构象、路易斯酸和螯合/非螯合控制与立体选择性之间的关系。
• A Regioselective Synthesis of Dimethyl Phthalide-3-phosphonates
  作者：Mitsuaki Watanabe、Saori Ijichi、Sunao Furukawa

  DOI：10.1055/s-1993-25807

  日期：——

  Dimethyl phthalide-3-phosphonates having various substituents on the benzene ring were regioselectively synthesized by the reaction of N,N-diethyl-2-formylbenzamides with tert-butyldimethylsilyl dimethyl phosphite followed by treatment with methanesulfonic acid. N,N-Diethyl-2-formylbenzamides were regioselectively prepared by ortho lithiation-formylation of the corresponding benzamides.

  具有不同取代基的二甲基邻苯二甲酸酯-3-膦酸酯通过N,N-二乙基-2-甲酰基苯甲酰胺与叔丁基二甲基硅基二甲基膦酸酯反应，随后用甲磺酸处理，选择性合成。N,N-二乙基-2-甲酰基苯甲酰胺则通过相应苯甲酰胺的邻位锂化-甲酰化反应选择性制备。
• Asymmetric induction using atropisomers: Diastereoselective additions to 2-acyl-1-naphthamides
  作者：Jonathan Clayden、Neii Westlund、Francis X Wilson

  DOI：10.1016/0040-4039(96)01129-x

  日期：1996.7

  The amide group of 2-acyl-N,N-dialkyl-1-naphthamides, twisted perpendicular to the naphthyl ring, controls the stereoselectivity of attack of nucleophiles on the 2-substituent. Selectivities of >140:1 may be achieved with bulky nucleophiles, which attack anti to the N,N-dialkyl group.

  垂直于萘基环扭曲的2-酰基-N，N-二烷基-1-萘酰胺的酰胺基控制亲核试剂攻击2-取代基的立体选择性。的> 140选择性：1可与亲核试剂笨重，其攻击来实现抗到Ñ，Ñ二烷基团。
• Asymmetric Wittig reactions of chiral arsonium ylides. Part 2: Atroposelective olefination of axially chiral N,N-dialkyl 2-formyl-1-naphthamides
  作者：Wei-Min Dai、Chi Wai Lau

  DOI：10.1016/s0040-4039(01)00193-9

  日期：2001.3

  Atroposelective olefination of axially chiral N,N-dialkyl 2-formyl-1-naphthamides with chiral ligand-derived stable arsonium ylides proceeded in a kinetic resolution manner. The (E)-olefin products were obtained in excellent chemical yields and in up to 88:12 diastereoselectivity. Effects of the amide alkyl groups, metal counter ions and solvents on the diastereoselectivity were investigated.

  轴向手性N，N-二烷基2-甲酰基-1-萘酰胺与手性配体衍生的稳定ar鎓的对映选择性催化烯化反应以动力学拆分的方式进行。以优异的化学产率和高达88:12的非对映选择性获得了（E）-烯烃产物。研究了酰胺烷基，金属抗衡离子和溶剂对非对映选择性的影响。
• Kinetic Resolution of Atropisomeric Amides
  作者：Ramon Rios、Ciril Jimeno、Patrick J. Carroll、Patrick J. Walsh

  DOI：10.1021/ja026436r

  日期：2002.9.1

  We have demonstrated the feasibility of the kinetic resolution of atropisomeric amides using the commercially avaliable AD-mix. To our knowledge, this methodology represents the first catalytic kinetic resolution of such compounds. Relative rates of up to 32 have been found for the kinetic resolution processes. We have also determined the barriers to rotation and half-lives of some of these amides. The half-lives range from 7 to 135 h at room temperature.