(2R)-2-[(S)-azido(phenyl)methyl]oxirane | 944324-81-6

• 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: (2R)-2-[(S)-azido(phenyl)methyl]oxirane
• 英文别名: (R)-2-((S)-azido(phenyl)methyl)oxirane；(2R,3S)-2-(azido-phenyl-methyl)-oxirane
• CAS: 944324-81-6
• 化学式: C₉H₉N₃O
• 分子量: 175.19
• InChiKey: JTALHNNEVAVOKW-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  26.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R)-2-[(S)-azido(phenyl)methyl]oxirane 在 2,6-二甲基吡啶 、 sodium tetrahydroborate 、 sodium periodate 、 四氧化锇 、 三氟化硼乙醚 、 四丁基氟化铵 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 32.5h， 生成 tert-butyl (2S,3S)-3-hydroxy-2-phenylpiperidine-1-carboxylate
  参考文献：
  名称：

  Enantioselective synthesis of (+)-l-733,060

  摘要：

  An efficient enantioselective synthesis of (+)-L-733,060 from cinnamyl alcohol is described. The key steps include a Sharpless asymmetric epoxidation, a regioselective allyl opening of an epoxide and piperidine ring formation via a one pot Staudinger/aza-Wittig reaction. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.04.006
• 作为产物：
  描述：

  (2S,3S)-3-azido-2-hydroxy-3-phenylpropyl pivalate 在 4-二甲氨基吡啶 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (2R)-2-[(S)-azido(phenyl)methyl]oxirane
  参考文献：
  名称：

  Enantioselective synthesis of (+)-l-733,060

  摘要：

  An efficient enantioselective synthesis of (+)-L-733,060 from cinnamyl alcohol is described. The key steps include a Sharpless asymmetric epoxidation, a regioselective allyl opening of an epoxide and piperidine ring formation via a one pot Staudinger/aza-Wittig reaction. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.04.006

文献信息

• Co(iii)(salen)-catalyzed HKR of two stereocentered alkoxy- and azido epoxides: a concise enantioselective synthesis of (S,S)-reboxetine and (+)-epi-cytoxazone
  作者：R. Santhosh Reddy、Pandurang V. Chouthaiwale、Gurunath Suryavanshi、Vilas B. Chavan、Arumugam Sudalai

  DOI：10.1039/c0cc00650e

  日期：——

  The HKR of racemic syn- or anti- alkoxy- and azido epoxides catalyzed by Co(salen) complex affords a practical access to a series of enantioenriched syn- or anti- alkoxy- and azido epoxides and the corresponding 1,2-diols. This strategy has been successfully employed in the concise, enantioselective synthesis of bioactive molecules such as (S,S)-reboxetine and (+)-epi-cytoxazone.

  在 Co（salen）络合物催化下，外消旋的合成或反合成烷氧基和叠氮环氧化物的 HKR 提供了获得一系列对映体富集的合成或反合成烷氧基和叠氮环氧化物以及相应的 1,2 二醇的实用途径。这种策略已成功应用于简便、对映选择性合成生物活性分子，如 (S,S)-reboxetine 和 (+)-epi-cytoxazone 等。
• Phenolytic Kinetic Resolution of Azido and Alkoxy Epoxides
  申请人：Council of Scientific & Industrial Research

  公开号：US20140350276A1

  公开（公告）日：2014-11-27

  Disclosed herein is a single step catalytic process for the production of enantiomerically pure α-Aryloxy-α′-Azido/Alkoxy alcohols of formula (A). The invention, in particular discloses phenolytic kinetic resolution of racemic anti and syn azido/alkoxy epoxides to generate two stereocentres of high optical purities of formula (A).

  本文披露了一种用于生产对映纯α-芳氧基-α′-偶氮/烷氧基醇（化学式(A)）的单步催化过程。具体揭示了对光学纯度高的两个立体中心的立体异构体(A)的酚基动力学拆分方法，用于将外消旋反式和顺式偶氮/烷氧基环氧化物转化为。
• Discovery of Orally Active Hydroxyethylamine Based SPPL2a Inhibitors
  作者：Juraj Velcicky、Casey J. N. Mathison、Victor Nikulin、Daniel Pflieger、Robert Epple、Mihai Azimioara、Christopher Cow、Pierre-Yves Michellys、Pascal Rigollier、Daniel R. Beisner、Ursula Bodendorf、Danilo Guerini、Bo Liu、Ben Wen、Samantha Zaharevitz、Trixi Brandl

  DOI：10.1021/acsmedchemlett.9b00044

  日期：2019.6.13

  SPPL2a (Signal Peptide Peptidase Like 2a) is an intramembrane aspartyl protease engaged in the function of B-cells and dendritic cells. Despite being an attractive target for modulation of the immune system, selective SPPL2a inhibitors are barely described in the literature. Recently, we have disclosed a selective, small molecular weight agent SPL-707 which confirmed that pharmacological inhibition of SPPL2a leads to the accumulation of its substrate CD74/p8 and as a consequence to a reduction in the number of B-cells as well as myeloid dendritic cells in mice. In this paper we describe the discovery of novel hydroxyethylamine based SPPL2a inhibitors. Starting from a rather lipophilic screening hit, several iterative optimization cycles allowed for its transformation into a highly potent and selective compound 15 (SPL-410) which inhibited in vivo CD74/p8 fragment processing in mice at 10 mg/kg oral dose.
• [EN] PHENOLYTIC KINETIC RESOLUTION OF AZIDO AND ALKOXY EPOXIDES<br/>[FR] RÉSOLUTION CINÉTIQUE PHÉNOLYTIQUE D'AZIDO- ET D'ALCOXY-ÉPOXYDES
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2013093943A9

  公开（公告）日：2014-01-23
• US8975430B2
  申请人：——

  公开号：US8975430B2

  公开（公告）日：2015-03-10