(2R,αR)-1-[(α-methylbenzyl)aziridin-2-yl]methyl benzyl ether | 592531-10-7

• 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,αR)-1-[(α-methylbenzyl)aziridin-2-yl]methyl benzyl ether
• 英文别名: (R)-2-(benzyloxymethyl)-1-[(R)-1-phenylethyl]aziridine；(2R)-1-[(1R)-1-phenylethyl]-2-(phenylmethoxymethyl)aziridine
• CAS: 592531-10-7
• 化学式: C₁₈H₂₁NO
• 分子量: 267.371
• InChiKey: GSSBCOPWVHCCJL-AOQMIGQVSA-N

物化性质

• 沸点：
  353.8±17.0 °C(Predicted)
• 密度：
  1.093±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  12.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,αR)-1-[(α-methylbenzyl)aziridin-2-yl]methyl benzyl ether 在 copper(l) iodide 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.34h， 生成 (2R)-1-(benzyloxy)-N, 5-dimethyl-N-[(R)-1-phenylethyl]hexan-2-amine
  参考文献：
  名称：

  N-甲基叠氮鎓离子的烷基化开环和酪氨酸的正式合成

  摘要：

  稳定的2-取代的N-甲基叠氮鎓离子的烷基化开环反应在CuI的存在下与各种烷基或芳基溴化镁进行反应，以完全区域选择性和立体选择性的方式生成合成上有价值的和光学纯的烷基化无环胺。将其用于细胞毒性天然产物酪氨酸的正式合成。

  DOI：

  10.1021/ol202683k
• 作为产物：
  描述：

  溴甲苯 、 (R)-1-[(R)-α-甲基苄基)氮杂环丙烷-2-甲醇 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以95%的产率得到(2R,αR)-1-[(α-methylbenzyl)aziridin-2-yl]methyl benzyl ether
  参考文献：
  名称：

  稳定的叠氮鎓离子的制备及其开环。

  摘要：

  对映体纯的2-取代的1-苯基乙基-氮丙啶与三氟甲磺酸甲酯的反应生成了稳定的甲基叠氮鎓离子，该离子与包括腈在内的各种外部亲核试剂反应，生成了对合成有价值的光学纯无环胺衍生物，具有完全的区域选择性和立体选择性方式。

  DOI：

  10.1039/b809124b

文献信息

• Asymmetric Synthesis of Fluoroamines from Chiral Aziridines
  作者：Hyeonjeong Park、Doo-Ha Yoon、Hyun-Joon Ha、Se In Son、Won Koo Lee

  DOI：10.5012/bkcs.2014.35.3.699

  日期：2014.3.20

  E-mail: [e-mail] September 18, 2013, Accepted November 26, 2013Key Words : Fluoroamine, Chiral aziridine, Ring-opening reaction, Triethylamine trihydrofluorideThe fluorinated organic molecules have attracted greatattentions from synthetic and medicinal chemists with wideuse of various agrochemicals and pharmaceuticals.

  E-mail: [e-mail] 2013年9月18日接收, 2013年11月26日接受关键词: 氟胺, 手性氮丙啶, 开环反应, 三乙胺三氢氟酸氟化有机分子已引起合成化学家和药物化学家的广泛关注。农用化学品和药品。
• Alkylative Aziridine Ring-Opening Reactions
  作者：Jieun Choi、Taehwan Yu、Hyun-Joon Ha

  DOI：10.3390/molecules26061703

  日期：——

  In this study, the highly strained three-membered aziridine ring was successfully activated as the aziridinium ion by alkylation of the ring nitrogen with a methyl, ethyl or allyl group, which was followed by ring opening with external nucleophiles such as acetate and azide. Such alkylative aziridine ring opening provides an easy route for the synthesis of various N-alkylated amine-containing molecules

  在这项研究中，通过将环氮与甲基，乙基或烯丙基烷基化，然后用外部亲核试剂（如乙酸酯和叠氮化物）开环，高度应变的三元氮丙啶环被成功激活为叠氮鎓离子。这种烷基化氮丙啶开环为合成各种含N-烷基化胺的分子提供了一条简便的途径，同时在其α-或β-位上引入了外部亲核试剂。
• A novel dynamic kinetic resolution accompanied by intramolecular transesterification: asymmetric synthesis of a 4-hydroxymethyl-2-oxazolidinone from serinol derivatives
  作者：Shigeo Sugiyama、Shoko Watanabe、Takayuki Inoue、Rie Kurihara、Takahiro Itou、Keitaro Ishii

  DOI：10.1016/s0040-4020(03)00477-0

  日期：2003.5

  Reaction paths of the one-pot reaction of (R)-2-(alpha-methylbenzyl)amino-1,3-propanediol (1) and 2-chloroethyl chloroformate with DBU giving (4S,alphaR)-4-hydroxymethyl-3-(alpha-methylbenzyl)-2-oxazolidinone [(4S)-2] (94% de) were investigated. Intermediates of this reaction, 2-chloroethyl (2S)- and 2-chloroethyl (2R)-3-hydroxy-2-[(alphaR)-alpha-methylbenzyl]aminopropyl carbonates [(2S)-4 and (2R)-4], were synthesized individually. After the addition of DBU to the respective solution of the carbonate (2S)-4 and that of (2R)-4 in dichloromethane, the intramolecular transesteritication between (2S)-4 and (2R)-4 and the diastereoselective intramolecular cyclization proceeded to afford (4S)-2 in high diastereomeric excess. Therefore, two monocarbonates (2S)-4 and (2R)-4 were kinetically resolved by this cyclization during the intramolecular transesterification between (2S)-4 and (2R)-4. We found that this process involved dynamic kinetic resolution accompanied by intramolecular transesterification. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Alkylative Ring Opening of<i>N</i>-Methylaziridinium Ions and a Formal Synthesis of Tyroscherin
  作者：Doo-Ha Yoon、Philjun Kang、Won Koo Lee、Yongeun Kim、Hyun-Joon Ha

  DOI：10.1021/ol202683k

  日期：2012.1.20

  Alkylative ring-opening reactions of stable 2-substituted N-methylaziridinium ions proceeded with various alkyl- or arylmagnesium bromides in the presence of CuI to yield synthetically valuable and optically pure alkylated acyclic amines in a completely regio- and stereoselective manner. This was applied to a formal synthesis of the cytotoxic natural product tyroscherin.

  稳定的2-取代的N-甲基叠氮鎓离子的烷基化开环反应在CuI的存在下与各种烷基或芳基溴化镁进行反应，以完全区域选择性和立体选择性的方式生成合成上有价值的和光学纯的烷基化无环胺。将其用于细胞毒性天然产物酪氨酸的正式合成。
• The preparation of stable aziridinium ions and their ring-openings
  作者：Yongeun Kim、Hyun-Joon Ha、Sae Young Yun、Won Koo Lee

  DOI：10.1039/b809124b

  日期：——

  The reaction of enantiomerically pure 2-substituted 1-phenylethyl-aziridine with methyl trifluoromethanesulfonate generated a stable methylaziridinium ion, which was reacted with various external nucleophiles, including nitrile, to yield synthetically valuable and optically pure acyclic amine derivatives in a completely regio- and stereoselective manner.

  对映体纯的2-取代的1-苯基乙基-氮丙啶与三氟甲磺酸甲酯的反应生成了稳定的甲基叠氮鎓离子，该离子与包括腈在内的各种外部亲核试剂反应，生成了对合成有价值的光学纯无环胺衍生物，具有完全的区域选择性和立体选择性方式。