2-(methoxymethyl)-6-methylaniline | 1035570-51-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(methoxymethyl)-6-methylaniline
• CAS: 1035570-51-4
• 化学式: C₉H₁₃NO
• 分子量: 151.208
• InChiKey: VLOKSQREFFHWSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(methoxymethyl)-6-methylaniline 在 N-溴代丁二酰亚胺(NBS) 、 甲酸 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 (1E,2E)-N¹,N²-bis(4-bromo-2-(methoxymethyl)-6-methylphenyl)ethane-1,2-diimine
  参考文献：
  名称：

  N-芳基取代基上的侧链烷氧基提高了咪唑基亚烷基催化剂对Enal和Aldehyde的均烯酸酯环化反应的效率。

  摘要：

  由咪唑基亚烷基催化剂和α，β-不饱和醛在四面体中间体中进行的氢转移形成了共轭Breslow中间体。这是关键步骤，它通过向芳基醛中添加均烯酸酯来影响NHC催化的γ-丁内酯的形成效率。一种新型的邻位烷氧基侧基的咪唑基亚烷基催化剂描述了-N-芳基。这种催化剂有助于形成共轭的Breslow中间体。对提供γ-丁内酯的均烯酸酯环化反应速率常数的研究表明，在N-芳基取代基的适当位置引入氧原子可以提高咪唑基亚烷基催化剂的效率。结构和机理研究表明，烷氧基侧基可以靠近四面体中间体的质子，从而促进质子转移。

  DOI：

  10.1002/anie.202008631
• 作为产物：
  描述：

  2-氨基-3-甲基苯甲酸 在 lithium aluminium tetrahydride 、 硫酸 作用下， 以 四氢呋喃 为溶剂， 反应 19.0h， 生成 2-(methoxymethyl)-6-methylaniline
  参考文献：
  名称：

  转位的 Paternò–Büchi 反应

  摘要：

  使用阻转异构烯酰胺作为模型系统评估了在“转置 Paternò-Büchi”反应中利用烯烃的 ππ* 激发态代替羰基发色团的 nπ* 激发态的互补策略。基于光物理研究，激发态的性质和反应途径被破译，导致 atropselective 反应。由于光化学反应所需的轨道方法，这种激发态构型转换的新概念应该为控制光反应的立体化学过程铺平道路。

  DOI：

  10.1021/jacs.6b05936

文献信息

• Engaging electronic effects for atropselective [5+2]-photocycloaddition of maleimides
  作者：Ramya Raghunathan、Elango Kumarasamy、Steffen Jockusch、Angel Ugrinov、J. Sivaguru

  DOI：10.1039/c6cc02962k

  日期：——

  Atropisomeric maleimides were synthesized and subjected to atropselective [5+2]-photocycloaddition under direct irradiation to yield azepinone products with high enantio- (ee >98%) and diastereoselectivity (dr >98%).

  异构的马来酰亚胺被合成并在直接照射下经历异构选择性的[5+2]-光环加成反应，产生具有高对映选择性（ee >98%）和非对映选择性（dr >98%）的环庚酮产物。
• HETEROBICYCLO-SUBSTITUTED [1,2,4]TRIAZOLO[1,5-C]QUINAZOLIN-5-AMINE COMPOUNDS WITH A2A ANTAGONIST PROPERTIES
  申请人：ALI Amjad

  公开号：US20150361098A1

  公开（公告）日：2015-12-17

  Disclosed are compounds of Formula G1 (structurally represented): where “RG3” “Rd1” to “Rd4”, “n”, “m”, “p”, “W”, “X”, “Y”, and “Z” are defined herein which compounds are antagonists of A2A receptor. Disclosed herein also are uses of the compounds described herein as antagonists of the A2a receptor in the potential treatment or prevention of neurological disorders and diseases in which A2A receptors are involved. Disclosed herein also are pharmaceutical compositions comprising these compounds and uses of these pharmaceutical compositions.

  本文披露了G1式化合物（结构式表示）：其中“RG3”、“Rd1”至“Rd4”、“n”、“m”、“p”、“W”、“X”、“Y”和“Z”在此定义，这些化合物是A2A受体的拮抗剂。本文还披露了所述化合物作为A2A受体拮抗剂在潜在的涉及A2A受体的神经系统疾病的治疗或预防中的用途。本文还披露了包含这些化合物的制药组合物和这些制药组合物的用途。
• Heterobicyclo-substituted [1,2,4]triazolo[1,5-c]quinazolin-5-amine compounds with A2A anatagonist properties
  申请人：Merck Sharp & Dohme Corp.

  公开号：US10011615B2

  公开（公告）日：2018-07-03

  Disclosed are compounds of Formula G1: where “RG3”. “Rd1” to “Rd4”, “n”, “m”, “p”, “W”, “X”, “Y”, and “Z” are defined herein, which compounds are antagonists of A2A receptor. Disclosed herein also are uses of the compounds described herein as antagonists of the A2A receptor in the potential treatment or prevention of neurological disorders and diseases in which A2A receptors are involved. Disclosed herein also are pharmaceutical compositions comprising these compounds and uses of these pharmaceutical compositions.

  公开了式 G1 的化合物： 其中 "RG3"Rd1 "至 "Rd4"、"n"、"m"、"p"、"W"、"X"、"Y "和 "Z "在本文中定义，这些化合物是 A2A 受体的拮抗剂。本文还公开了本文所述化合物作为 A2A 受体拮抗剂在潜在治疗或预防涉及 A2A 受体的神经紊乱和疾病中的用途。本文还公开了包含这些化合物的药物组合物以及这些药物组合物的用途。
• Tailoring Atropisomeric Maleimides for Stereospecific [2 + 2] Photocycloaddition—Photochemical and Photophysical Investigations Leading to Visible-Light Photocatalysis
  作者：Elango Kumarasamy、Ramya Raghunathan、Steffen Jockusch、Angel Ugrinov、J. Sivaguru

  DOI：10.1021/ja5034638

  日期：2014.6.18

  Atropisomeric maleimides were synthesized and employed for stereospecific [2 + 2] photocycloaddition. Efficient reaction was observed under direct irradiation, triplet-sensitized UV irradiation, and non-metal catalyzed visible-light irradiation, leading to two regioisomeric (exo/endo) photoproducts with complete chemoselectivity (exclusive [2 + 2] photoproduct). High enantioselectivity (ee > 98%) and diastereoselectivity (dr > 99:1%) were observed under the employed reaction conditions and were largely dependent on the substituent on the maleimide double bond but minimally affected by the substituents on the alkenyl tether. On the basis of detailed photophysical studies, the triplet energies of the maleimides were estimated. The triplet lifetimes appeared to be relatively short at room temperature as a result of fast [2 + 2] photocycloaddition. For the visible-light mediated reaction, triplet energy transfer occurred with a rate constant close to the diffusion-limited value. The mechanism was established by generation of singlet oxygen from the excited maleimides. The high selectivity in the photoproduct upon reaction from the triplet excited state was rationalized on the basis of conformational factors as well as the type of diradical intermediate that was preferred during the photoreaction.
• US9708347B2
  申请人：——

  公开号：US9708347B2

  公开（公告）日：2017-07-18