benzyl (S)-2-benzylaziridine-1-carboxylate | 1142923-78-1

• 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: benzyl (S)-2-benzylaziridine-1-carboxylate
• 英文别名: (S)-benzyl-2-benzylaziridine-1-carboxylate；(S)-2-Benzylaziridine-carboxylate；benzyl (2S)-2-benzylaziridine-1-carboxylate
• CAS: 1142923-78-1
• 化学式: C₁₇H₁₇NO₂
• 分子量: 267.327
• InChiKey: QPCNEIYNSIZFAY-ATNAJCNCSA-N

物化性质

• 沸点：
  402.9±24.0 °C(Predicted)
• 密度：
  1.210±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  29.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  benzyl (S)-2-benzylaziridine-1-carboxylate 在 silver tetrafluoroborate 、 2,6-双(二苯基膦甲基)吡啶二氯化钯 、 三氟甲磺酸三甲基硅酯 、 三氟化硼乙醚 、 magnesium sulfate 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  使用钯催化的加氢氨化反应立体选择性合成2，5-二取代的吗啉。

  摘要：

  钯催化的加氢胺化反应是从氨基甲酸酯保护的氮丙啶立体选择性合成2，5-二取代和2,3,5-三取代吗啉的关键步骤。使用路易斯酸催化剂，不饱和醇亲核试剂选择性地在更取代的位置上攻击氮丙啶。所得氨基烯烃的钯催化加氢胺化反应可将吗啉作为单一非对映异构体以极佳的收率得到。

  DOI：

  10.1039/c3cc44117b
• 作为产物：
  描述：

  S-2-苄基氮杂环丙烷 、 苄基氰基甲酸酯 以 乙腈 为溶剂， 反应 0.08h， 生成 benzyl (S)-2-benzylaziridine-1-carboxylate
  参考文献：
  名称：

  Synthesis of novel N-protected β3-amino nitriles: study of their hydrolysis involving a nitrilase-catalyzed step

  摘要：

  Several commercially available nitrilases were investigated with regard to their potential to hydrolyze N-protected beta(3)-amino nitriles into their corresponding N-protected beta(3)-amino acids.The biotransformations were obtained in different proportions depending oil the nitrilase involved The best hydrolysis results were achieved for the N-Cbz-beta(3)-amino nitrile from i-alanine using the NIT-107, in a phosphate buffer at 0 05 M However, no biotransformation into the corresponding acids was observed for the N-sulfonylamide beta(3)-amino nitriles. Two simple and efficient procedures to prepare the beta(3)-amino nitriles from their analogous alpha-amino acids are described Thirty four new substances were synthesized and characterized over the course of this work. (C) 2009 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tetasy.2009.07.045

文献信息

• Synthesis of Aminomethylene-<i>gem</i>-bisphosphonates Containing an Aziridine Motif: Studies of the Reaction Scope and Insight into the Mechanism
  作者：Thomas Cheviet、Suzanne Peyrottes

  DOI：10.1021/acs.joc.0c02434

  日期：2021.2.19

  Study of the reaction’s scope and additional experiments indicates that the transformation proceeds via a new mechanism involving the chelation of lithium ion. This last step is crucial for the reaction to occur and disfavors the aziridine ring-opening. A phosphonate–phosphate rearrangement from a α-hydroxybisphosphonate aziridine intermediate is also proposed for the first time. This reaction provides

  获得了广泛的N-氨基甲酰基氮丙啶，然后用二乙基膦酸根阴离子处理，得到α-亚甲基-宝石-双膦酸酯氮丙啶。对反应范围和其他实验的研究表明，转化是通过涉及锂离子螯合的新机理进行的。这最后一步对于反应的发生至关重要，不利于氮丙啶开环。还首次提出了由α-羟基双膦酸酯氮丙啶中间体进行的膦酸酯-磷酸重排。该反应提供了用于合成高度官能化的膦酰化氮丙啶基序的简单方便的方法。
• One-Pot Synthesis of β-Amino/β-Hydroxy Selenides and Sulfides from Aziridines and Epoxides
  作者：Srinivasan Chandrasekaran、Venkataraman Ganesh

  DOI：10.1055/s-0029-1216960

  日期：2009.10

  Diaryl disulfides and diselenides undergo facile cleavage on treatment with rongalite (sodium hydroxymethanesulfinate) to generate the corresponding thiolate and selenolate species in situ, which effect the ring opening of aziridines and epoxides in a regio­selective manner. A simple, mild, cost-effective protocol has been developed to prepare β-amino and β-hydroxy sulfides and selenides in a one-pot operation.

  二芳基二硫和二硒化物在与隆伽利特（羟甲基亚磺酸钠）反应时容易发生裂解，生成相应的硫醇盐和硒醇盐物种，这些物质能够选择性地促进氮杂环和环氧化物的开环反应。已开发出一种简单、温和、成本效益高的一锅法操作，用于制备β-氨基和β-羟基硫化物和硒化物。
• Synthesis of <i>N</i>-methylene phosphonate aziridines: reaction scope and mechanistic insights
  作者：Thomas Cheviet、Ilyana Gonzales、Suzanne Peyrottes

  DOI：10.1039/d2nj00595f

  日期：——

  A series of N-carbamoyl aziridines has been treated by diethyl phosphite in the presence of n-BuLi to afford α-methylene phosphonate aziridines in modest yields. The study of the reaction's scopes and the analysis of byproducts indicated that this transformation proceeds via a unique mechanism. The mechanism that produces the α-methylene phosphonate relies on the use of BuLi, where both the lithium

  在n -BuLi存在下，用亚磷酸二乙酯处理一系列N-氨基甲酰基氮丙啶，以适中的收率得到 α-亚甲基膦酸氮丙啶。对反应范围的研究和对副产物的分析表明，这种转变是通过一种独特的机制进行的。产生 α-亚甲基膦酸酯的机制依赖于 BuLi 的使用，其中锂离子和亲核丁基的存在都是必不可少的。此外，最终化合物（α-亚甲基膦酸酯或含有氮丙啶基序的 α-亚甲基偕二膦酸酯衍生物）的性质高度依赖于所用碱的性质。
• Ring opening of aziridines with ortho-bromophenyl metal reagents: synthesis of 2-substituted indolines
  作者：David J. Michaelis、Thomas A. Dineen

  DOI：10.1016/j.tetlet.2009.02.047

  日期：2009.4

  Stabilized ortho-bromo phenyllithium reagents, generated via lithium-halogen exchange of aryl iodides, undergo regioselective ring opening of mono-substituted N-Boc, N-Cbz, and N-tosyl-protected aziridines in good to excellent yields. The resulting ortho-bromo phenethylamines can be cyclized under transition-metal-catalyzed conditions to give 2-substituted chiral, non-racemic indolines in good yields. (C) 2009 Elsevier Ltd. All rights reserved.