N-benzyl-1-[(3S)-1,4-dioxaspiro[4.5]decan-3-yl]methanimine | 1333213-22-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-benzyl-1-[(3S)-1,4-dioxaspiro[4.5]decan-3-yl]methanimine
• CAS: 1333213-22-1
• 化学式: C₁₆H₂₁NO₂
• 分子量: 259.348
• InChiKey: GDBJNTWGTVNULR-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  30.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-benzyl-1-[(3S)-1,4-dioxaspiro[4.5]decan-3-yl]methanimine 在 cerium(III) chloride heptahydrate 、 四丁基溴化铵 、 碳酸氢钠 、 锌 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 5.0h， 生成 (S)-N-allyl-N-benzyl-1-((S)-1,4-dioxaspiro[4.5]decan-2-yl)but-3-en-1-amine
  参考文献：
  名称：

  An improved method of ring closing metathesis in the presence of basic amines: application to the formal synthesis of (+)-lentiginosine and other piperidines and carbamino sugar analogs

  摘要：

  A generalized method for performing ring closing metathesis in the presence of basic amines has been established and successfully used in the formal synthesis of (+)-lentiginosine as well as some valuable intermediates for the synthesis of several other azasugars and aminocyclitols. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.12.020
• 作为产物：
  描述：

  (R)-1,4-二氧杂螺[4,5]癸烷-2-甲醛 、 苄胺 在 magnesium sulfate 作用下， 以 乙醚 为溶剂， 反应 0.5h， 生成 N-benzyl-1-[(3S)-1,4-dioxaspiro[4.5]decan-3-yl]methanimine
  参考文献：
  名称：

  An improved method of ring closing metathesis in the presence of basic amines: application to the formal synthesis of (+)-lentiginosine and other piperidines and carbamino sugar analogs

  摘要：

  A generalized method for performing ring closing metathesis in the presence of basic amines has been established and successfully used in the formal synthesis of (+)-lentiginosine as well as some valuable intermediates for the synthesis of several other azasugars and aminocyclitols. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.12.020

文献信息

• Enantiodivergent Synthetic Entry to the Quinolizidine Alkaloid Lasubine II
  作者：Nemai Saha、Tanmoy Biswas、Shital K Chattopadhyay

  DOI：10.1021/ol2019967

  日期：2011.10.7

  Intramolecular cycloaddition of the syn- and the anti-nitrone 9 and 13 leads stereoselectively to the azabicyclic compounds 10 and 14 which may provide access to both enantiomers of the quinolizidine alkaloid lasubine II.

  顺式-和反-硝基化合物9和13的分子内环加成立体选择性地导致了氮杂双环化合物10和14，其可以提供与喹喔啉生物碱Lasubine II的两种对映异构体的接近。
• Enantiodivergent synthesis of N-protected azetidine-2-carboxylic acid
  作者：Tanmoy Biswas、Jyoti Prasad Mukherjee、Shital K. Chattopadhyay

  DOI：10.1016/j.tetasy.2012.08.016

  日期：2012.10

  A new route to both enantiomers of N-tosyl-azetidine-2- carboxylic acid has been developed from (R)-2-cyclohexylideneglyceraldehyde which proceeded with good overall yield and excellent enantiomeric purity. (C) 2012 Elsevier Ltd. All rights reserved.
• Diastereoselective Allylation of α-Hydroxy Schiff Bases with 2-Substituted Functionalized Allyl Bromides
  作者：I. V. Mineeva

  DOI：10.1134/s1070428021090086

  日期：2021.9
• Methyl 3-(Bromomethyl)but-3-enoate and Methyl 3-[(Tributylstannyl)methyl]but-3-enoate in Azomethine Allylation Reactions
  作者：D. A. Snetkov、I. V. Mineeva

  DOI：10.1134/s1070428020080011

  日期：2020.8

  Allylation of azomethines was demonstrated for the first time on examples of methyl 3-(bromomethyl)-but-3-enoate and methyl 3-[(tributylstannyl)methyl]but-3-enoate. Various systems for the allylation of azomethines under the Barbier reaction conditions were studied and tested. Evidence for the possibility of the addition of allylating agents derived from 3-[(tributylstannyl)methyl]but-3-enoate to azomethines of various structures was obtained.