(S)-N-benzyl-1-((S)-1,4-dioxaspiro[4.5]decan-2-yl)but-3-en-1-amine | 1268685-02-4

• 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: (S)-N-benzyl-1-((S)-1,4-dioxaspiro[4.5]decan-2-yl)but-3-en-1-amine
• 英文别名: (1S)-N-benzyl-1-[(3S)-1,4-dioxaspiro[4.5]decan-3-yl]but-3-en-1-amine
• CAS: 1268685-02-4
• 化学式: C₁₉H₂₇NO₂
• 分子量: 301.429
• InChiKey: COJQXIBLSDFNRN-ZWKOTPCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-N-benzyl-1-((S)-1,4-dioxaspiro[4.5]decan-2-yl)but-3-en-1-amine 在 20 % Pd(OH)2/C 、 氢气 、 三氟乙酸 作用下， 以 甲醇 、 水 为溶剂， 反应 1.33h， 生成 (2S,3S)-3-tert-butoxycarbonylamino-1,2-hexanediol
  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：

  苄胺 在 magnesium sulfate 作用下， 以 四氢呋喃 为溶剂， 反应 34.17h， 生成 (S)-N-benzyl-1-((S)-1,4-dioxaspiro[4.5]decan-2-yl)but-3-en-1-amine
  参考文献：
  名称：

  Enantiodivergent synthesis of N-protected azetidine-2-carboxylic acid

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2012.08.016

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.
• 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
  作者：Rima Lahiri、Hari Prasad Kokatla、Yashwant D. Vankar

  DOI：10.1016/j.tetlet.2010.12.020

  日期：2011.2

  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.