N-benzylideneisobutylamine | 27845-49-4

• 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-benzylideneisobutylamine
• CAS: 27845-49-4
• 化学式: C₁₁H₁₅N
• 分子量: 161.247
• InChiKey: ZZFNBVPVZOECOF-FMIVXFBMSA-N

物化性质

• 熔点：
  119 °C
• 沸点：
  238.0±9.0 °C(Predicted)
• 密度：
  0.87±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.76
• 重原子数：
  12.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  12.36
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  N-benzylideneisobutylamine 在 溶剂黄146 、 1-丙基磷酸酐 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 32.0h， 生成
  参考文献：
  名称：

  Hit-to-Lead Studies for the Antimalarial Tetrahydroisoquinolone Carboxanilides

  摘要：

  Phenotypic whole-cell screening in erythrocytic cocultures of Plasmodium falciparum identified a series of dihydroisoquinolones that possessed potent antimalarial activity against multiple resistant strains of P. falciparum in vitro and show no cytotoxicity to mammalian cells. Systematic structure activity studies revealed relationships between potency and modifications at N-2, C-3, and C-4. Careful structure property relationship studies, coupled with studies of metabolism, addressed the poor aqueous solubility and metabolic vulnerability, as well as potential toxicological effects, inherent in the more potent primary screening hits such as 10b. Analogues 13h and 13i, with structural modifications at each site, were shown to possess excellent antimalarial activity in vivo. The (+)-(35,4S) enantiomer of 13i and similar analogues were identified as the more potent. On the basis of these studies, we have selected (+)-13i for further study as a preclinical candidate.

  DOI：

  10.1021/acs.jmedchem.6b00752
• 作为产物：
  描述：

  异丁胺 、 苯甲醛 以90%的产率得到N-benzylideneisobutylamine
  参考文献：
  名称：

  亚胺基亚胺在亚氨基醇上的1,3-偶极环加成反应：使用无溶剂条件合成新的咪唑啉酮

  摘要：

  在70°C或微波辐射下，与1,3-恶唑烷的互变异构平衡中，衍生自α-氨基酯的亚磺酸盐（作为潜在的甲亚胺基化物）与亚氨基醇进行1,3-偶极环加成反应，与1,3-恶唑烷呈互变异构平衡。该反应以短的反应时间以良好的收率产生了多种新型的多官能化的4-yliden-2-imidazolin-5-one。由半经验PM3计算确定的前沿分子轨道（FMO）的能量合理化了这些衍生自α-氨基酯的亚胺与亚氨基醇的反应性：该反应由HOMO （1,3-偶极）相互作用控制） - LUMO （亲偶极）和第二级摄动能量的计算是与实验反应取向一致。

  DOI：

  10.1016/0040-4020(95)00321-x

文献信息

• Synthesis of five-membered heterocycles containing a nitrogen-oxygen bond via O-acylation of aliphatic nitro compounds.
  作者：KAZUHO HARADA、EISUKE KAJI、SHONOSUKE ZEN

  DOI：10.1248/cpb.28.3296

  日期：——

  O-Acylation of primary aliphatic nitro compounds with acid chlorides in N, N-dimethylacetamide led to the formation of nitrile oxides, which cyclized in situ with olefinic dipolarophiles in a 1, 3-dipolar cycloaddition mode to afford 2-isoxazoline derivatives. Optimum reaction conditions were investigated, and the use of several types of dipolarophiles, such as acetylenes, Schiff bases, aromatic nitriles, and ketones, in this cycloaddition resulted in the formation of the corresponding cycloadducts, namely isoxazoles, 1, 2, 4-oxadiazolines, 1, 2, 4-oxadiazoles, and 1, 4, 2-dioxazoles, respectively, in reasonable yields.

  初级脂肪族硝基化合物与酸氯化物在N,N-二甲基乙酰胺中进行O-酰化反应，形成了腈氧化物，这些腈氧化物与烯烃类双极试剂在1,3-双极环加成模式下原位环化，生成了2-异噁唑啉衍生物。研究了最佳反应条件，使用多种类型的双极试剂，如炔烃、施夫碱、芳香族腈和酮类，进行这一环加成反应，分别合理产率地生成了相应的环加成产物，即异噁唑、1,2,4-噁二唑啉、1,2,4-噁二唑以及1,4,2-二噁唑。
• Nuclear magnetic resonance and infrared spectra of some aldimines (azomethines)
  作者：K. A. W. Parry、P. J. Robinson、P. J. Sainsbury、M. J. Waller

  DOI：10.1039/j29700000700

  日期：——

  N.m.r. and i.r. spectra are reported for 19 imines of the type PC[graphic omitted]N–C[graphic omitted]QR (P = alkyl or aryl and Q, R =(H,alk), (alk,alk), or –[CH2]n–). The variation in |Jab| with structure is examined, and evidence is found for conformational effects similar to those for allylic coupling. The CN stretching frequencies fall into characteristic and separate ranges for P = alkyl and P

  报告了19种亚胺PC [Graphic] N–C [Graphic] QR（P =烷基或芳基和Q，R =（H，alk），（alk，alk）或– [CH 2 ] n –）。|中的变化 J ab | 研究了具有结构的结构，并发现了构象效应与烯丙基偶联相似的证据。对于P ＝烷基和P ＝芳基，C N的拉伸频率落入特征和单独的范围，但是较好的效果通常并不明显。
• Indium mediated Barbier-type allylation of aldimines in alcoholic solvents
  作者：Tirayut Vilaivan、Chutima Winotapan、Tetsuro Shinada、Yasufumi Ohfune

  DOI：10.1016/s0040-4039(01)01977-3

  日期：2001.12

  Barbier-type allylation of unactivated aldimines with allyl bromides in the presence of indium powder took place rapidly in alcoholic solvents to give homoallylic amines in fair to good yields.

  在铟粉存在下，未活化的亚胺与烯丙基溴的Barbier型烯丙基化反应在醇类溶剂中迅速发生，从而以均等到良好的收率得到均烯丙基胺。
• 1,3-Dipolar cycloaddition of imidate ylides on imino-alcohols: Synthesis of new imidazolones using solvent free conditions
  作者：Jean Michel Lerestif、Jacques Perrocheau、François Tonnard、Jean Pierre Bazureau、Jack Hamelin

  DOI：10.1016/0040-4020(95)00321-x

  日期：1995.6

  Imidates derived from α-amino esters as potential azomethine ylides, undergo 1,3-dipolar cycloaddition with imino-alcohols, in tautomeric equilibrium with 1,3-oxazolidines, without solvent at 70°C or under microwave irradiation. This reaction leads to a wide range of novel polyfunctionalized 4-yliden-2-imidazolin-5-ones in good yields with short reaction times. The reactivity of these imidates derived

  在70°C或微波辐射下，与1,3-恶唑烷的互变异构平衡中，衍生自α-氨基酯的亚磺酸盐（作为潜在的甲亚胺基化物）与亚氨基醇进行1,3-偶极环加成反应，与1,3-恶唑烷呈互变异构平衡。该反应以短的反应时间以良好的收率产生了多种新型的多官能化的4-yliden-2-imidazolin-5-one。由半经验PM3计算确定的前沿分子轨道（FMO）的能量合理化了这些衍生自α-氨基酯的亚胺与亚氨基醇的反应性：该反应由HOMO （1,3-偶极）相互作用控制） - LUMO （亲偶极）和第二级摄动能量的计算是与实验反应取向一致。
• [EN] PROCESS FOR THE PREPARATION OF (3R,3AS,6AR)-HEXAHYDROFURO [2,3-B] FURAN-3-YL (1S,2R)-3-[[(4-AMINOPHENYL) SULFONYL] (ISOBUTYL) AMINO]-1-BENZYL-2-HYDROXYPROPYLCARBAMATE<br/>[FR] PROCÉDÉ DE PRÉPARATION DU COMPOSÉ (3R,3AS,6AR)-HEXAHYDROFURO[2,3-B]FURAN-3-YL(1S,2R)-3-[[(4-AMINOPHÉNYL) SULFONYL](ISOBUTYL)AMINO]-1-BENZYL-2-HYDROXYPROPYLCARBAMATE
  申请人：TIBOTEC PHARM LTD

  公开号：WO2010023322A1

  公开（公告）日：2010-03-04

  The present invention relates to a process for the preparation of (3R,3a S,6aR)-hexa-hydrofuro [2,3-b] furan-3-yl (1S,2R)-3-[[(4-aminophenyl) sulfonyl] (isobutyl) amino]-1-benzyl-2-hydroxypropylcarbamate as well as novel intermediates for use in said process. (3R,3a S,6aR)-hexahydrofuro [2,3-b] furan-3-yl (1S,2R)-3-[[(4-aminophenyl) sulfonyl] (isobutyl) amino]-1-benzyl-2-hydroxypropylcarbamate is particularly useful as an HIV protease inhibitor.

  本发明涉及一种制备(3R,3a S,6aR)-六氢呋喃[2,3-b]呋喃-3-基(1S,2R)-3-[[（4-氨基苯基）磺酰](异丁基)氨基]-1-苄基-2-羟基丙基氨基甲酸酯的方法，以及用于该方法的新型中间体。(3R,3a S,6aR)-六氢呋喃[2,3-b]呋喃-3-基(1S,2R)-3-[[（4-氨基苯基）磺酰](异丁基)氨基]-1-苄基-2-羟基丙基氨基甲酸酯特别适用作为HIV蛋白酶抑制剂。