(S)-2-isobutylaziridine | 23852-57-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环丙烷
• 英文名称: (S)-2-isobutylaziridine
• 英文别名: (S)-2-(2-Methylpropyl)-aziridine；(2S)-2-(2-Methylpropyl)aziridine
• CAS: 23852-57-5
• 化学式: C₆H₁₃N
• 分子量: 99.1759
• InChiKey: KGHFQEDPQOKCSJ-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  21.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-2-isobutylaziridine 在 palladium on activated charcoal 氢气 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 67.0h， 生成 -phenylmethyl 2-<<<2-<<<2-(1,1-dimethylethoxy)-2-oxoethyl>amino>methyl>-3-methylbutyl>amino>carbonyl>-1-pyrrolidinecarboxylate
  参考文献：
  名称：

  Modified di- and tripeptides of the C-terminal portion of oxytocin and vasopressin as possible cognition activation agents

  摘要：

  A number of peptides and modified peptides were synthesized and studied for their ability to reverse electroconvulsive shock-induced amnesia in rodents. A few of these peptides were selected for secondary evaluation in tests of short-term memory in rats and aged rhesus monkeys. A number of the peptides and modified peptides were active in the amnesia reversal test. In selected secondary tests, however, the chosen compounds failed to show significant activity in enhancing memory. New methods for preparing methyleneamino and methyleneoxy isosteres of peptides are reported. Other modified peptides also included methylenethio, methylenesulfonyl, and ethylene isosteres in place of the normal peptide amide bond.

  DOI：

  10.1021/jm00156a012
• 作为产物：
  描述：

  L-亮氨醇 在 4-二甲氨基吡啶 、 copper(l) iodide 、 sodium hydride 、 三乙胺 、 对甲苯磺酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 31.33h， 生成 (S)-2-isobutylaziridine
  参考文献：
  名称：

  N-二苯基亚膦酰基氮丙啶的制备及开环反应

  摘要：

  单手性N-二苯膦基氮丙啶可以由单手性2-氨基醇有效地制备。这样的氮丙啶与各种亲核试剂以良好的产率进行开环反应。脱膦酰基化是在温和的条件下完成的。

  DOI：

  10.1016/s0040-4020(97)10430-6

文献信息

• Efficient Synthesis of Taurine and Structurally Diverse Substituted Taurines from Aziridines
  作者：Libo Hu、Hui Zhu、Da-Ming Du、Jiaxi Xu

  DOI：10.1021/jo070470c

  日期：2007.6.1

  Taurine and substituted taurines were synthesized efficiently from aziridines via ring-opening reaction with thioacetic acid, oxidation with performic acid, and hydrolysis in hydrochloric acid. The current method shows more benefit in purification and efficiency in the preparation of taurine and structurally diverse 2-substituted, 2,2-disubstituted, and 1,2-, 2,2-, and 2,N-alkylene taurines.

  通过与硫代乙酸的开环反应，过甲酸的氧化和在盐酸中的水解，由氮丙啶有效地合成了牛磺酸和取代的牛磺酸。当前的方法在制备牛磺酸和结构上不同的2-取代的，2，2-二取代的和1，2-，2，2-和2，N-亚烷基牛磺酸中，在纯化和效率上显示出更多的益处。
• A Versatile Synthesis of Various Substituted Taurines from Vicinal Amino Alcohols and Aziridines
  作者：Ning Chen、Weiyi Jia、Jiaxi Xu

  DOI：10.1002/ejoc.200900759

  日期：2009.11

  Taurine and structurally diverse substituted taurines have been synthesized by peroxyformic acid oxidation of the thiazolidine-2-thione intermediates generated from vicinal amino alcohols or aziridines and carbon disulfide. Thestereochemistry and mechanisms of the reactions are disscussed. The method is a salt-free and versatile route, convenient in terms of purification, and can be used to synthesize

  牛磺酸和结构不同的取代牛磺酸已经通过由邻氨基醇或氮丙啶和二硫化碳产生的噻唑烷-2-硫酮中间体的过氧甲酸氧化合成。讨论了反应的立体化学和机理。该方法为无盐通用路线，纯化方便，可用于合成光学活性取代牛磺酸。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Phosphinoyl-aziridines as a new class of chiral catalysts for enantioselective Michael addition
  作者：Zuzanna Wujkowska、Anna Zawisza、Stanisław Leśniak、Michał Rachwalski

  DOI：10.1016/j.tet.2018.11.052

  日期：2019.1

  series of new optically pure phosphine oxides containing chiral aziridine subunit were synthesized in good yields and applied as organocatalysts in asymmetric Michael reaction of various aliphatic aldehydes with β-nitrostyrene. The corresponding organocatalysts were synthesized starting from optically pure aziridines in a few simple efficient steps. The appropriate Michael adducts were obtained in most

  以高收率合成了一系列含有手性氮丙啶亚基的新型光学纯氧化膦，并将其用作有机催化剂，用于各种脂肪族醛与β-硝基苯乙烯的不对称迈克尔反应。在几个简单有效的步骤中，从光学纯的氮丙啶开始合成相应的有机催化剂。在大多数情况下，可以以很高的化学收率（最高97％），出色的对映选择性（最高ee的98％）和非对映选择性（最高dr的95：5 ）获得合适的迈克尔加合物。
• Synthesis of chiral 1-(2-aminoalkyl)aziridines via the self-opening reaction of aziridine
  作者：Adam M. Pieczonka、Ewelina Misztal、Michał Rachwalski、Stanisław Leśniak

  DOI：10.3998/ark.5550190.p009.741

  日期：——

  A novel approach to the synthesis of optically pure 1-(2-aminoalkyl)aziridines via a nucleophilic ring-opening reaction of aziridine is presented. The reaction takes place under mild conditions in the presence of ZnBr2 with moderate chemical yields. The formation of 1-(2-aminoalkyl)aziridines, starting from optically pure NHaziridines, occurs selectively, leading to a single diastereoisomer.

  提出了一种通过氮丙啶的亲核开环反应合成光学纯 1-(2-氨基烷基) 氮丙啶的新方法。该反应在温和条件下在 ZnBr2 存在下以中等化学产率进行。1-（2-氨基烷基）氮丙啶的形成，从光学纯的 NH 氮丙啶开始，选择性地发生，导致单一的非对映异构体。
• Modified tripeptides
  申请人：Warner-Lambert Company

  公开号：US04596819A1

  公开（公告）日：1986-06-24

  Modified oxytocin-vasopressin di- or tri-peptides wherein an amide group is replaced by a group selected from ##STR1## --CH.sub.2 NH--, --CH.sub.2 O--, --CH.sub.2 S--, --CH.sub.2 SO--, --CH.sub.2 SO.sub.2 --, --CH.sub.2 CH.sub.2 -- and --CH.dbd.CH-- are described as well as methods for their manufacture, pharmaceutical compositions and methods for treatment, especially of cognitive disorders, depression, morphine dependency and parkinsonism by adjunctive therapy.

  修改后的催产素-加压素二肽或三肽，其中酰胺基团被选择自##STR1## --CH.sub.2 NH--, --CH.sub.2 O--, --CH.sub.2 S--, --CH.sub.2 SO--, --CH.sub.2 SO.sub.2 --, --CH.sub.2 CH.sub.2 -- 和 --CH.dbd.CH--的基团替代，以及它们的制备方法、药物组合物和治疗方法，特别是通过辅助疗法治疗认知障碍、抑郁症、吗啡依赖症和帕金森症。