N-(tert-butyloxycarbonyl)-1-naphthylmethylamine | 344551-27-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(tert-butyloxycarbonyl)-1-naphthylmethylamine
• 英文别名: tert-butyl ester [(1-naphthyl)methyl]-carbamic acid；tert-butyl (naphthalen-1-ylmethyl)carbamate；naphthalen-1-ylmethyl-carbamic acid tert-butyl ester；N-nathphalen-1-ylmethyl-tert-butyl carbamate；tert-butyl N-(naphthalen-1-ylmethyl)carbamate
• CAS: 344551-27-5
• 化学式: C₁₆H₁₉NO₂
• 分子量: 257.332
• InChiKey: FGHOYJMOQHTQIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(tert-butyloxycarbonyl)-1-naphthylmethylamine 在 仲丁基锂 、 三乙胺 、 鹰爪豆碱 作用下， 以 二氯甲烷 、 环己烷 、 甲苯 为溶剂， 反应 3.33h， 生成 (alphaS)-alpha-[[(1,1-二甲基乙氧基)羰基]氨基]-1-萘乙酸
  参考文献：
  名称：

  通过苄基锂化反应快速获得N- Boc苯基甘氨酸衍生物

  摘要：

  我们报告了一种新型有效的方法，用于N- Boc保护的苯基甘氨酸的对映选择性合成。产率和对映体比率根据溶剂，底物的性质和形成手性络合物的方法而有很大差异。结果表明，主要反应途径是对映选择性去质子化/取代过程。对映选择性似乎受s -BuLi-（-）-天冬氨酸络合物的手性鉴别能力的限制。所述的合成方法是获得有用的对映体富集的N- Boc苯基甘氨酸衍生物的最短途径之一。

  DOI：

  10.1016/s0040-4020(01)00159-4
• 作为产物：
  描述：

  1-萘甲醇 在 sodium tetrahydroborate 、 sodium carbonate 、 溶剂黄146 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 丙醇 、 水 为溶剂， 反应 27.0h， 生成 N-(tert-butyloxycarbonyl)-1-naphthylmethylamine
  参考文献：
  名称：

  Improved synthesis of (R)-glycine-d-15N

  摘要：

  Previously, we have synthesized the title glycine to permit assignment of the prochiral alpha -protons of glycine residues in the NMR study of the protein FKBP. A key, and low yielding step in this synthesis occurs in the ruthenium tetraoxide mediated degradation of N-t-Boc-p-methoxybenzyl amine to N-t-Boc-glycine. Efforts to improve this key step by exploring different substrates and N-protecting groups were successful to render this synthesis amenable for the large scale production of (R)-glycine-d-N-15. (C) 2001 Elsevier Science Ltd. Ail rights reserved.

  DOI：

  10.1016/s0040-4020(01)00629-9

文献信息

• One-Pot Synthesis of α-Amino Acids from Imines through CO2 Incorporation: An Alternative Method for Strecker Synthesis
  作者：Tsuyoshi Mita、Jianyang Chen、Masumi Sugawara、Yoshihiro Sato

  DOI：10.1002/anie.201006422

  日期：2011.2.7

  It′s a gas: A novel one‐pot process for the synthesis of α‐amino acids from imine equivalents using CO2 gas as a carbon source has been developed. This reaction was made possible by the reagent combination of TMSSnBu3 and CsF (see scheme). Three successive reactions (imine formation, stannylation, and carboxylation) proceeded in the same flask under these conditions to give products in up to 79 % yield

  它是一种气体：已开发出一种新颖的单罐方法，该方法使用CO 2气体作为碳源，从亚胺当量合成α-氨基酸。通过TMSSnBu 3和CsF的试剂结合使该反应成为可能（参见方案）。在这些条件下，在同一烧瓶中进行了三个连续的反应（亚胺形成，甲氧基化和羧化），以最高79％的收率得到产物。Boc =叔丁氧羰基，TMS =三甲基甲硅烷基。
• Metal‐Free Visible‐Light Induced Oxidative Cleavage of C(sp³)−C, and C(sp³)−N Bonds of Nitriles, Alcohols, and Amines
  作者：Ishani Borthakur、Abhisek Joshi、Saloni Kumari、Sabuj Kundu

  DOI：10.1002/chem.202303295

  日期：2024.3.7

  This work presents a visible-light mediated oxidative cleavage of unstrained C−C(sp3) and C−N(sp3) bonds of nitriles, alcohols (diols), and amines using Acr+-Mes/Selectfluor/DMAP system and O2 as the oxidant.

  这项工作提出了使用 Acr + -Mes/Selectflu/DMAP 系统和 O 对腈、醇（二醇）和胺的无张力 C−C(sp 3 ) 和 C−N(sp 3 ) 键进行可见光介导的氧化裂解2作为氧化剂。
• Suzuki–Miyaura Cross-Coupling Reactions of Potassium Boc-Protected Aminomethyltrifluoroborate with Aryl and Hetaryl Mesylates
  作者：Gary A. Molander、Inji Shin

  DOI：10.1021/ol301221p

  日期：2012.6.15

  Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions were studied with potassium Boc-protected aminomethyltrifluoroborate through C-O activation of various mesylate derivatives to afford the corresponding products in moderate to good yields.
• Pd-Catalyzed Suzuki–Miyaura Cross-Coupling Reactions between Sulfamates and Potassium Boc-Protected Aminomethyltrifluoroborates
  作者：Gary A. Molander、Inji Shin

  DOI：10.1021/ol401021x

  日期：2013.5.17

  Sulfamates were studied as the electrophilic partners in the palladium-catalyzed Suzuki-Miyaura cross-coupling reaction with potassium Boc-protected primary and secondary aminomethyltrifluoroborates. A broad range of substrates was successfully coupled to provide the desired products. Complex molecules containing a new carbon-carbon bond and an aminomethyl moiety could be prepared through this developed method.
• Blocking Estrogen Signaling After the Hormone: Pyrimidine-Core Inhibitors of Estrogen Receptor-Coactivator Binding
  作者：Alexander A. Parent、Jillian R. Gunther、John A. Katzenellenbogen

  DOI：10.1021/jm800698b

  日期：2008.10.23

  As an alternative approach to blocking estrogen action, we have developed small molecules that directly disrupt the key estrogen receptor (ER)/coactivator interaction necessary for gene activation. The more direct, protein-protein nature of this disruption might be effective even in hormone-refractory breast cancer. We have synthesized a pyrimidine-core library of moderate size, members of which act as a-helix mimics to block the ER alpha/coactivator interaction. Structure-activity relationships have been explored with various C-, N-, O-, and S-substituents on the pyrimidine core. Time-resolved fluorescence resonance energy transfer and cell-based reporter gene assays show that the most active members inhibit the ER alpha/steroid receptor coactivator interaction with Ki's in the low micromolar range. Through these studies, we have obtained a refined pharmacophore model for activity in this pyrimidine series. Furthermore, the favorable activities of several of these compounds support the feasibility that this coactivator binding inhibition mechanism for blocking estrogen action might provide a potential alternative approach to endocrine therapy.