(2S,3S)-2-Methoxymethoxymethyl-3-pentyl-oxirane | 496941-83-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: (2S,3S)-2-Methoxymethoxymethyl-3-pentyl-oxirane
• 英文别名: (2S,3S)-2-(methoxymethoxymethyl)-3-pentyloxirane
• CAS: 496941-83-4
• 化学式: C₁₀H₂₀O₃
• 分子量: 188.267
• InChiKey: WUVFRVNAKIHKQW-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  31
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3S)-2-Methoxymethoxymethyl-3-pentyl-oxirane 在 吡啶 、 sodium azide 、 氯化铵 作用下， 以 乙二醇甲醚 、 水 为溶剂， 反应 36.33h， 生成 (2S,3R)-2-(methoxymethoxymethyl)-1-(4-methylphenylsulfonyl)-3-pentylaziridine
  参考文献：
  名称：

  Base-promoted elaboration of aziridines

  摘要：

  The base-promoted isomerization of aziridines to allyl amines is still an almost unknown reaction. However, the use of superbasic reagents has shown to be able to promote a regio- and stereoselective conversion of monocyclic and bicyclic sulfonyl aziridines. Moreover, the use of alkoxy substituted aziridines opens new routes to non-natural alpha- and beta-amino acids. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00729-9
• 作为产物：
  描述：

  [(2S,3S)-3-pentyloxiran-2-yl]methanol 、 氯甲基甲基醚 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以87%的产率得到(2S,3S)-2-Methoxymethoxymethyl-3-pentyl-oxirane
  参考文献：
  名称：

  Base promoted isomerization of aziridinyl ethers: a new access to α- and β-amino acidsElectronic supplementary information (ESI) available: experimental procedures and NMR data. See http://www.rsc.org/suppdata/cc/b2/b200708h/.

  摘要：

  氮丙啶基醚经混合金属碱（超级碱）处理后，可选择性地轻松转化为氨基乙烯基醚或烷氧基烯丙基胺。

  DOI：

  10.1039/b200708h

文献信息

• Base promoted isomerization of aziridinyl ethers: a new access to α- and β-amino acidsElectronic supplementary information (ESI) available: experimental procedures and NMR data. See http://www.rsc.org/suppdata/cc/b2/b200708h/.
  作者：Alessandro Mordini、Laura Sbaragli、Michela Valacchi、Francesco Russo、Gianna Reginato

  DOI：10.1039/b200708h

  日期：2002.3.21

  Aziridinyl ethers are selectively and easily converted to either amino vinyl ethers or alkoxy allylamines by treatment with mixed metal bases (superbases).

  氮丙啶基醚经混合金属碱（超级碱）处理后，可选择性地轻松转化为氨基乙烯基醚或烷氧基烯丙基胺。
• Heteroatom-Assisted Isomerization of Oxiranes to Allylic Alcohols Promoted by Bases
  作者：Alessandro Mordini、Sabina Pecchi、Giuseppe Capozzi、Antonella Capperucci、Alessandro Degl'Innocenti、Gianna Reginato、Alfredo Ricci

  DOI：10.1021/jo00096a020

  日期：1994.8

  The isomerization of alkoxy-substituted oxiranes to hydroxy-substituted ene ethers promoted by mixed metal bases has been investigated. The structure of the oxirane substrate (the number, the position, and the type of alkyl substituents on the ring) plays an important role in driving the stereoselectivity of the reaction. Disubstituted oxiranes show a predictable preference for the E-ene ether while trisubstituted substrates give either a mixture of stereoisomers or the E-ene ether exclusively, depending on the location of the third alkyl substituent.
• Base-promoted elaboration of aziridines
  作者：Alessandro Mordini、Francesco Russo、Michela Valacchi、Lorenzo Zani、Alessandro Degl'Innocenti、Gianna Reginato

  DOI：10.1016/s0040-4020(02)00729-9

  日期：2002.8

  The base-promoted isomerization of aziridines to allyl amines is still an almost unknown reaction. However, the use of superbasic reagents has shown to be able to promote a regio- and stereoselective conversion of monocyclic and bicyclic sulfonyl aziridines. Moreover, the use of alkoxy substituted aziridines opens new routes to non-natural alpha- and beta-amino acids. (C) 2002 Elsevier Science Ltd. All rights reserved.