N-(naphthalen-1-ylmethyl)cyclohexanamine | 14489-84-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(naphthalen-1-ylmethyl)cyclohexanamine
• CAS: 14489-84-0
• 化学式: C₁₇H₂₁N
• mdl: MFCD07409404
• 分子量: 239.36
• InChiKey: UJBGPGGAPUZPGI-UHFFFAOYSA-N

物化性质

• 沸点：
  386.6±11.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.411
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(naphthalen-1-ylmethyl)cyclohexanamine 在 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 邻二甲苯 为溶剂， 反应 9.0h， 生成 1-萘甲醛
  参考文献：
  名称：

  Dehydrogenation of amines. An approach to imines and aldehydes

  摘要：

  DOI：

  10.1021/jo00335a076
• 作为产物：
  描述：

  α-naphtylidene-N-cyclohexylimine 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.33h， 生成 N-(naphthalen-1-ylmethyl)cyclohexanamine
  参考文献：
  名称：

  Synthesis and structure-activity relationships of naftifine-related allylamine antimycotics

  摘要：

  Naftifine (1) is the first representative of the new antifungal allylamine derivatives. Its biological activity is strictly bound to specific structural requirements that are unrelated to those of known antifungals. A tertiary allylamine function seems to be a prerequisite for activity against fungi. By systematic variation of the individual structural elements in 1, detailed structure-activity relationships are defined in which the phenyl ring is the structural feature permitting the widest variations. Versatile synthetic routes to allylamine derivatives and comparative biological data are presented.

  DOI：

  10.1021/jm00151a019

文献信息

• Rapid and Efficient Access to Secondary Arylmethylamines
  作者：Nicolas Fleury-Brégeot、Jessica Raushel、Deidre L. Sandrock、Spencer D. Dreher、Gary A. Molander

  DOI：10.1002/chem.201200831

  日期：2012.7.27

  Ammoniomethyl trifluoroborates are very powerful reagents that can be used to access biologically relevant aryl‐ and heteroaryl‐methylamine motifs via Suzuki–Miyaura cross‐couplings. Until now, this method was limited to the production of tertiary and primary amines. The synthesis of a large array of secondary ammoniomethyltrifluoroborates has been achieved through a one step nucleophilic substitution

  氨甲基三氟硼酸盐是非常强大的试剂，可用于通过 Suzuki-Miyaura 交叉偶联获得生物学相关的芳基和杂芳基甲胺基序。到目前为止，这种方法仅限于生产叔胺和伯胺。通过对溴甲基三氟硼酸钾的一步亲核取代反应，合成了大量仲氨甲基三氟硼酸盐。基于氨基联苯钯预催化剂的使用，设计了平滑的交叉偶联条件，以有效地将这些三氟硼酸盐与芳基溴化物偶联。该策略提供了一种访问生物学相关基序的新方法，并允许使用先前开发的方法访问所有三类氨甲基芳烃。
• Metal-Free Formal Oxidative C−C Coupling by In Situ Generation of an Enolonium Species
  作者：Daniel Kaiser、Aurélien de la Torre、Saad Shaaban、Nuno Maulide

  DOI：10.1002/anie.201701538

  日期：2017.5.15

  contemporary organic synthesis relies on transformations that are driven by the intrinsic, so‐called “natural”, polarity of chemical bonds and reactive centers. The design of unconventionally polarized synthons is a highly desirable strategy, as it generally enables unprecedented retrosynthetic disconnections for the synthesis of complex substances. Whereas the umpolung of carbonyl centers is a well‐known

  当代许多有机合成都依赖于化学键和反应中心固有的，所谓的“天然”极性驱动的转变。非常规极化合成子的设计是非常需要的策略，因为它通常能够实现复杂物质合成的空前的逆合成断开。羰基中心的空位化是众所周知的策略，而羰基α位的极性反转要少得多。在本文中，我们报告了一种新型亲电子en烯的设计及其在高效和化学选择性，无金属的氧化C-C偶联中的应用。
• Aminoalkyl naphthalenediols as host resistance enhancers against viral infection
  申请人：Merck & Co., Inc.

  公开号：EP0393256A1

  公开（公告）日：1990-10-24

  Disclosed are specific aminoalkyl naphthalenediol derivatives that enhance natural human host resistance to viral infectious organisms and particularly AIDS-related viruses. Such agents are also administered prophylactically to individuals whose resistance to infection has been specifically immunocompromised by an AIDS-related (HIV) virus.

  披露了特定的氨基烷基萘二酚衍生物，可以增强自然人类宿主对病毒感染性生物体，尤其是艾滋病相关病毒的抵抗力。这些药物也可以预防性地给那些因艾滋病相关（HIV）病毒而特别免疫功能受损导致感染风险增加的个体使用。
• In Situ-Generated Iodonium Ylides as Safe Carbene Precursors for the Chemoselective Intramolecular Buchner Reaction
  作者：Shanyan Mo、Xinhao Li、Jiaxi Xu

  DOI：10.1021/jo501628h

  日期：2014.10.3

  A chemoselective intramolecular Buchner reaction employing iodonium ylides as safe carbene precursors has been developed. Iodonium ylides are generated in situ from N-benzyl-2-cyanoacetamides and PhI(OAc)2 in the presence of base and undergo intramolecular Buchner reaction under catalysis from Cu(OAc)2·H2O, affording fused cyclohepta-1,3,5-triene derivatives in up to 85% yield. The N,N-dibenzyl-2-cyanoacetamides

  已经开发了使用碘化碘化物作为安全的卡宾前体的化学选择性分子内布氏反应。N-苄基-2-氰基乙酰胺和PhI（OAc）2在碱的存在下原位生成碘鎓碘化物，并在Cu（OAc）2 ·H 2 O催化下进行分子内布氏反应，得到稠合的环庚-1,3 ，5-三烯衍生物的产率高达85％。该ñ，ñ具有两个不同苄基的-二苄基-2-氰基乙酰胺选择性地在其富电子的苄基上进行分子内布赫纳反应。该反应对空气和湿气不敏感，并使用相应重氮原料的安全替代形式。已经验证了涉及卡宾途径的整体转化。
• Sodium Hypophosphite as a Bulk and Environmentally Friendly Reducing Agent in the Reductive Amination
  作者：Fedor Kliuev、Anton Kuznetsov、Oleg I. Afanasyev、Sofiya A. Runikhina、Ekaterina Kuchuk、Evgeniya Podyacheva、Alexey A. Tsygankov、Denis Chusov

  DOI：10.1021/acs.orglett.2c02807

  日期：2022.10.28

  NaH2PO2 was found to promote reductive amination. Being nontoxic, stable, environmentally benign, and available in bulk amounts, this reducing agent showed a powerful potential to compete with classical reductants applied in the target process. An E factor of 1 was achieved for the substrate scope. Different carbonyl compounds reacted with amines under the developed conditions. The reaction demonstrated

  发现NaH 2 PO 2促进还原胺化。这种还原剂无毒、稳定、对环境无害且可大量使用，显示出与目标工艺中应用的经典还原剂竞争的强大潜力。底物范围的E因子为 1。在开发的条件下，不同的羰基化合物与胺反应。该反应显示出与多种官能团的良好相容性。反应条件放大至 200 倍。