(E)-[2-(tert-butyldimethylsilyloxy)ethyl](3-phenylpropenylidine)amine | 557763-60-7

• 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: (E)-[2-(tert-butyldimethylsilyloxy)ethyl](3-phenylpropenylidine)amine
• 英文别名: [2-(tert-butyldimethylsilyloxy)ethyl][(E)-3-phenylpropenylidene]amine；(E)-N-[2-[tert-butyl(dimethyl)silyl]oxyethyl]-3-phenylprop-2-en-1-imine
• CAS: 557763-60-7
• 化学式: C₁₇H₂₇NOSi
• 分子量: 289.493
• InChiKey: BSTAAAWMWFMRNJ-OAPNILDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.79
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-[2-(tert-butyldimethylsilyloxy)ethyl](3-phenylpropenylidine)amine 在 copper(ll) sulfate pentahydrate 、 氯化铵 、 三乙胺 、 对甲苯磺酰氯 、 锌 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 3.0h， 生成 (5R,6S)-6-amino-5-[(E)-2-phenylethenyl]-1,4-oxazepan-7-one
  参考文献：
  名称：

  Cu-promoted single-pot intramolecular esterification of C-3 functionalized azetidin-2-one: an efficient diastereoselective access to azido-/amino-aza-lactones

  摘要：

  A facile, single pot diastereoselective access to seven and eight membered aza-heterocycles was developed by using beta-lactam-synthon approach. The developed protocol does not involve the typical intricacies viz. the use of expensive transition metal catalysts and high boiling solvents, associated with the convenient protocols. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.05.016
• 作为产物：
  描述：

  肉桂醛 在 3 A molecular sieve 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 13.0h， 生成 (E)-[2-(tert-butyldimethylsilyloxy)ethyl](3-phenylpropenylidine)amine
  参考文献：
  名称：

  Synthesis of Intramolecularly Activated Lactenediynes and Evaluation of Their Activity Against Plasmid DNA

  摘要：

  The synthesis of new "selectively activated" enediyne prodrugs is reported. These compounds, belonging to the "lactenediyne" family, each possess a protected primary amine tethered at the beta-lactam nitrogen. This, once deblocked, can act as a trigger, provoking a cascade of events probably terminating with Bergman cycloaromatization of the enediyne moiety. In vitro experiments on plasmid DNA have shown that the protected compounds are inactive, while the unprotected amine is able to provoke single-strand scissions. These results open the way towards development of enzymatically activated lactenediyne prodrugs.

  DOI：

  10.1002/1099-0690(200211)2002:22<3745::aid-ejoc3745>3.0.co;2-c

文献信息

• Intramolecular Opening of β-Lactams with Amines as a Strategy Toward Enzymatically or Photochemically Triggered Activation of Lactenediyne Prodrugs
  作者：Luca Banfi、Giuseppe Guanti、Marcello Rasparini

  DOI：10.1002/ejoc.200390188

  日期：2003.3

  to develop a general strategy for selective activation of designed enediyne prodrugs belonging to the “lactenediyne” family, we studied the scope of intramolecular transamidation of simple monocyclic β-lactams bearing a tethered amine. The effect of substituents, of reaction media, and of the type of tether, on the rate of transamidation is disclosed. The possibility of triggering the transamidation

  为了开发选择性激活属于“lactenediyne”家族的设计的烯二炔前药的一般策略，我们研究了带有束缚胺的简单单环 β-内酰胺的分子内转酰胺化的范围。公开了取代基、反应介质和系链类型对转酰胺化速率的影响。在模型单环 β-内酰胺上证明了在温和条件下通过合适的酶或紫外线的作用触发转酰胺事件的可能性。最后，β-内酰胺分子内打开导致更大的七元环的策略被用于乳糖二炔，证明环扩大可以释放烯二炔部分的反应性。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
• Cu-promoted single-pot intramolecular esterification of C-3 functionalized azetidin-2-one: an efficient diastereoselective access to azido-/amino-aza-lactones
  作者：Kewal Kumar、Sumit Kumar、Tejinder Singh、Amit Anand、Vipan Kumar

  DOI：10.1016/j.tetlet.2014.05.016

  日期：2014.7

  A facile, single pot diastereoselective access to seven and eight membered aza-heterocycles was developed by using beta-lactam-synthon approach. The developed protocol does not involve the typical intricacies viz. the use of expensive transition metal catalysts and high boiling solvents, associated with the convenient protocols. (C) 2014 Elsevier Ltd. All rights reserved.
• Synthesis of Intramolecularly Activated Lactenediynes and Evaluation of Their Activity Against Plasmid DNA
  作者：Luca Banfi、Giuseppe Guanti

  DOI：10.1002/1099-0690(200211)2002:22<3745::aid-ejoc3745>3.0.co;2-c

  日期：2002.11

  The synthesis of new "selectively activated" enediyne prodrugs is reported. These compounds, belonging to the "lactenediyne" family, each possess a protected primary amine tethered at the beta-lactam nitrogen. This, once deblocked, can act as a trigger, provoking a cascade of events probably terminating with Bergman cycloaromatization of the enediyne moiety. In vitro experiments on plasmid DNA have shown that the protected compounds are inactive, while the unprotected amine is able to provoke single-strand scissions. These results open the way towards development of enzymatically activated lactenediyne prodrugs.