(+/-)-N,N-dibenzylalaninal | 129286-74-4

• 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: (+/-)-N,N-dibenzylalaninal
• 英文别名: 2-(Dibenzylamino)propanal
• CAS: 129286-74-4
• 化学式: C₁₇H₁₉NO
• 分子量: 253.344
• InChiKey: GFYXFRCVQSKSDO-UHFFFAOYSA-N

物化性质

• 沸点：
  346.2±30.0 °C(Predicted)
• 密度：
  1.067±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+/-)-N,N-dibenzylalaninal 在 钯 氢气 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， -78.0 ℃ 、101.33 kPa 条件下， 生成 1-benzyl-2-methyl-4,5,6,7-tetrahydro-1H-indole
  参考文献：
  名称：

  A versatile synthesis of polysubstituted pyrroles

  摘要：

  The aldol products formed by the reaction between alpha-(N-benzyl or N-Cbz)amino aldehydes and lithium enolates of various ketones, were subjected to hydrogenolysis to give polysubstituted pyrroles in good yields (50-91%). The scope and limitations of this methodology are explored. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01203-5
• 作为产物：
  描述：

  2-(dibenzylamino)propan-1-ol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (+/-)-N,N-dibenzylalaninal
  参考文献：
  名称：

  Parallel Kinetic Resolution of Acyclic γ-Amino-α,β-unsaturated Esters: Application to the Asymmetric Synthesis of 4-Aminopyrrolidin-2-ones

  摘要：

  Conjugate addition of a 50:50 pseudoenantiomeric mixture of lithium (R)-N-benzyl-N(alpha-methylbenzyl)amide and lithium (S)-N-3,4-dimethoxybenzyl-N-(alpha-methylbenzyl)amide to a range of racemic acyclic gamma-amino-alpha,beta-unsaturated esters (derived from the corresponding a-amino acids) effects their efficient parallel kinetic resolution, allowing the preparation of enantiopure beta,gamma-diamino esters. The beta,gamma-dlamlno ester products of these reactions are readily converted into the corresponding substituted 4-aminopyrrolidin-2-ones via N-debenzylation and cyclization.

  DOI：

  10.1021/ol203011u

文献信息

• AMPHOTERICIN B DERIVATIVES WITH IMPROVED THERAPEUTIC INDEX
  申请人：THE BOARD OF TRUSTEES OF THE UNIVERSITY OF ILLINOIS

  公开号：US20160215012A1

  公开（公告）日：2016-07-28

  Provided are certain derivatives of amphotericin B (AmB) characterized by reduced toxicity and retained anti-fungal activity. Certain of the derivatives are C16 urea derivatives of AmB. Certain of the derivatives are C3, C5, C8, C9, C11, C13, or C15 deoxy derivatives of AmB. Certain of the derivatives include C3′ or C4′ modifications of the mycosamine appendage of AmB. Also provided are methods of making AmB derivatives of the invention, pharmaceutical compositions comprising AmB derivatives of the invention, and methods of use of AmB derivatives of the invention.

  提供了一些特定的两性霉素B（AmB）衍生物，其具有降低毒性和保留抗真菌活性的特点。其中一些衍生物是AmB的C16脲衍生物。其中一些衍生物是AmB的C3、C5、C8、C9、C11、C13或C15去氧衍生物。其中一些衍生物包括对AmB的甲氨葡萄糖胺附属物的C3′或C4′修饰。还提供了制备该发明的AmB衍生物的方法，包括该发明的AmB衍生物的药物组合物，以及该发明的AmB衍生物的使用方法。
• [EN] UREA DERIVATIVES OF AMPHOTERICIN B DERIVED FROM SECONDARY AMINES<br/>[FR] DÉRIVÉS D'URÉE DE L'AMPHOTÉRICINE B DÉRIVÉE D'AMINES SECONDAIRES
  申请人：UNIV ILLINOIS

  公开号：WO2016112243A1

  公开（公告）日：2016-07-14

  Provided are certain urea derivatives of amphotericin B (AmB) having improved therapeutic index compared to AmB. The compounds of the invention are less toxic than AmB and are useful to treat fungal infections. In certain embodiments the urea derivative of AmB is a compound represented by formula (I) or a pharmaceutically acceptable salt thereof: wherein, independently for each occurrence: R represents methyl, ethyl, propyl, or isopropyl; R' represents methyl, ethyl, propyl, or isopropyl; or R and R', taken together with the nitrogen atom to which they are attached, represent a radical of a cyclic secondary amine. Also provided are methods for making the urea derivatives of AmB.

  提供了与两性霉素B（AmB）相比具有改善的治疗指数的某些尿素衍生物。本发明的化合物比AmB毒性更小，并且可用于治疗真菌感染。在某些实施例中，AmB的尿素衍生物是由以下式（I）表示的化合物或其药用可接受的盐：其中，对于每次出现独立地：R代表甲基、乙基、丙基或异丙基；R'代表甲基、乙基、丙基或异丙基；或R和R'与它们连接的氮原子一起表示环状二级胺的基团。还提供了制备AmB的尿素衍生物的方法。
• [EN] CONCISE SYNTHESIS OF UREA DERIVATIVES OF AMPHOTERICIN B<br/>[FR] SYNTHÈSE CONCISE DE DÉRIVÉS D'URÉE D'AMPHOTÉRICINE B
  申请人：UNIV ILLINOIS

  公开号：WO2016112260A1

  公开（公告）日：2016-07-14

  Provided are certain derivatives of amphotericin B (AmB) characterized by reduced toxicity and retained anti -fungal activity. Certain of the derivatives are C16 urea derivatives and C16 carbamate derivatives of AmB. Also provided are methods of making the AmB derivatives.

  提供了某些特征为降低毒性并保留抗真菌活性的两性霉素B（AmB）衍生物。其中某些衍生物是AmB的C16脲衍生物和C16氨基甲酸酯衍生物。还提供了制备AmB衍生物的方法。
• Efficient Addition Reaction of Bromonitromethane to Aldehydes Catalyzed by NaI:  A New Route to 1-Bromo-1-nitroalkan-2-ols under Very Mild Conditions
  作者：José M. Concellón、Humberto Rodríguez-Solla、Carmen Concellón、Santiago García-Granda、M. Rosario Díaz

  DOI：10.1021/ol062451f

  日期：2006.12.1

  [Structure: see text] A catalytic NaI-mediated novel synthesis of 1-bromo-1-nitroalkan-2-ols was carried out by reaction of bromonitromethane with a variety of aldehydes, under very mild conditions. When the reaction was performed with chiral N,N-dibenzyl alaninal, the corresponding enantiopure (1S,2S,3S)-3-dibenzylamino-1-bromo-1-nitrobutan-2-ol was obtained with good stereoselectivity. The structure

  [结构：见正文]在非常温和的条件下，通过溴硝基甲烷与各种醛的反应，进行了NaI介导的新型催化1-溴-1-硝基烷-2-醇的合成。当用手性N，N-二苄基丙氨酸进行反应时，以良好的立体选择性得到相应的对映纯（1S，2S，3S）-3-二苄基氨基-1-溴-1-硝基丁烷-2-醇。通过X射线分析确定该对映体纯的溴代醇的结构。
• [EN] PYRROLO [2, 3 - B] PYRAZINE - 7 - CARBOXAMIDE DERIVATIVES AND THEIR USE AS JAK AND SYK INHIBITORS<br/>[FR] DÉRIVÉS DE PYRROLO[2,3-B]PYRAZINE-7-CARBOXAMIDE ET LEUR UTILISATION COMME INHIBITEURS DE JAK ET SYK
  申请人：HOFFMANN LA ROCHE

  公开号：WO2011144585A1

  公开（公告）日：2011-11-24

  The present invention relates to the use of novel pyrrolopyrazine derivatives of Formula (I), wherein the variables Q and R, R2, and R3 are defined as described herein, which inhibit JAK and SYK and are useful for the treatment of auto-immune and inflammatory diseases.

  本发明涉及使用式（I）的新型吡咯吡嗪衍生物，其中变量Q和R，R2和R3如本文所述定义，其抑制JAK和SYK并且适用于治疗自身免疫和炎症性疾病。