1-(4-甲氧基苯基)-N-(2-萘基甲基)甲胺 | 355816-03-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1-(4-甲氧基苯基)-N-(2-萘基甲基)甲胺
• 英文名称: (2-naphthylmethyl)-4-methoxybenzylamine
• 英文别名: (4-Methoxybenzyl)(2-naphthylmethyl)amine；1-(4-methoxyphenyl)-N-(naphthalen-2-ylmethyl)methanamine
• CAS: 355816-03-4
• 化学式: C₁₉H₁₉NO
• 分子量: 277.366
• InChiKey: QFASUHSSHNOXCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-甲氧基苯基)-N-(2-萘基甲基)甲胺 在 4-乙酰氨基苯磺酰叠氮 、 Ru-pheox 、 sodium acetate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 2.02h， 生成 C₂₁H₂₁NO₂
  参考文献：
  名称：

  使用 Ru(II)-Pheox 配合物从萘基重氮乙酰胺高度对映选择性合成去甲卡二烯衍生物

  摘要：

  本文报道了萘基重氮乙酰胺的高度区域和对映选择性分子内环丙烷化反应。在 Ru( II )-Pheox 催化剂存在下，通过卡宾转移反应从相应的重氮乙酰胺中以高收率（高达 99%）和高对映选择性（高达 99% ee）获得手性和稳定的去甲卡二烯衍生物。

  DOI：

  10.1039/d2cc04355f
• 作为产物：
  描述：

  (E)-N-[(4-Methoxyphenyl)methyl]-1-(naphthalen-2-yl)methanimine 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以736 mg的产率得到1-(4-甲氧基苯基)-N-(2-萘基甲基)甲胺
  参考文献：
  名称：

  Allosteric Functional Switch of Neurokinin A-Mediated Signaling at the Neurokinin NK2 Receptor: Structural Exploration

  摘要：

  The neurokinin NK2 receptor is known to pre-exist in equilibrium between at least three states: resting-inactive, calcium-triggering, and cAMP-producing. Its endogeneous ligand, NKA, mainly induces the calcium response. Using a FRET-based assay, we have previously discovered an allosteric modulator of the NK2 receptor that has the unique ability to discriminate among the two signaling pathways: calcium-signaling is not affected while CAMP signaling is significantly decreased. A series of compounds have been prepared and studied in order to better understand the structural determinants of this allosteric functional switch of a GPCR. Most of them display the same allosteric profile, with smooth pharmacomodulation. One compound however exhibits significantly improved modulatory properties of NKA induced signaling when compared to the original modulator.

  DOI：

  10.1021/jm900671k

文献信息

• Thermal Rearrangement of Sulfamoyl Azides: Reactivity and Mechanistic Study
  作者：Xiaodong Zou、Jiaqi Zou、Lizheng Yang、Guigen Li、Hongjian Lu

  DOI：10.1021/acs.joc.7b00308

  日期：2017.5.5

  The rearrangement of sulfamoyl azides under thermal conditions to form a C–C bond while breaking two C–N bonds is reported. Mechanistic study shows that this reaction goes through a Curtius-type rearrangement to form a 1,1-diazene, then which rearranges possibly through both a concerted rearrangement process and a stepwise radical process. This rearrangement could be used in the synthesis of complex

  据报道，在热条件下，氨磺酰叠氮化物会重排形成一个C–C键，同时打破两个C–N键。机理研究表明，该反应经过库尔修斯式重排形成1，1-二氮杂苯，然后可能通过协同重排过程和逐步自由基过程进行重排。该重排可用于合成复杂的生物活性分子，例如固醇和胡椒碱衍生物。
• Reductive Amination of Aldehydes Using Aminoboranes as Iminium Ion Generators
  作者：Michinori Suginome、Yusuke Tanaka、Tomoaki Hasui

  DOI：10.1055/s-2006-939070

  日期：——

  2-Dialkylamino-4H-1,3,2-benzodioxaborins, salicyl alcohol derived aminoboranes, serve as efficient and mild iminium ion generators in the reductive amination of aldehydes with NaBH4. Using a diisopropylamino derivative, a variety of amines including secondary and primary amines, and ammonia can participate to the reductive amination in aprotic organic solvents without the use of acidic promoters.

  2-二烷基氨基-4H-1,3,2-苯并二氧硼烷和基于水杨醇的氨基硼烷在与NaBH4的还原胺化反应中，作为高效且温和的亚胺离子生成剂。使用二异丙基氨基衍生物，二级和初级胺以及氨可以在无质子有机溶剂中参与还原胺化，而无需使用酸性促进剂。
• Allosteric Functional Switch of Neurokinin A-Mediated Signaling at the Neurokinin NK2 Receptor: Structural Exploration
  作者：Céline Valant、Emeline Maillet、Jean-Jacques Bourguignon、Bernard Bucher、Valérie Utard、Jean-Luc Galzi、Marcel Hibert

  DOI：10.1021/jm900671k

  日期：2009.10.8

  The neurokinin NK2 receptor is known to pre-exist in equilibrium between at least three states: resting-inactive, calcium-triggering, and cAMP-producing. Its endogeneous ligand, NKA, mainly induces the calcium response. Using a FRET-based assay, we have previously discovered an allosteric modulator of the NK2 receptor that has the unique ability to discriminate among the two signaling pathways: calcium-signaling is not affected while CAMP signaling is significantly decreased. A series of compounds have been prepared and studied in order to better understand the structural determinants of this allosteric functional switch of a GPCR. Most of them display the same allosteric profile, with smooth pharmacomodulation. One compound however exhibits significantly improved modulatory properties of NKA induced signaling when compared to the original modulator.
• Highly enantioselective synthesis of norcaradiene derivatives from naphthyl diazoacetamides using a Ru(<scp>ii</scp>)-Pheox complex
  作者：Nansalmaa Otog、Bilguun Gantogos、Ikuhide Fujisawa、Seiji Iwasa

  DOI：10.1039/d2cc04355f

  日期：——

  The highly regio- and enantioselective intramolecular cyclopropanation reactions of naphthyl diazoacetamides have been reported herein. In the presence of a Ru(II)-Pheox catalyst, chiral and stable norcaradiene derivatives were obtained from the corresponding diazoacetamides via carbene transfer reactions in high yields (up to 99%) and with high enantioselectivities (up to 99% ee).

  本文报道了萘基重氮乙酰胺的高度区域和对映选择性分子内环丙烷化反应。在 Ru( II )-Pheox 催化剂存在下，通过卡宾转移反应从相应的重氮乙酰胺中以高收率（高达 99%）和高对映选择性（高达 99% ee）获得手性和稳定的去甲卡二烯衍生物。