methyl (S)-2-(diallylamino)propanoate | 847899-95-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (S)-2-(diallylamino)propanoate
• 英文别名: N,N-bis-allyl-L-alanine methyl ester；methyl 2-diallylaminopropionate；methyl (2S)-2-[bis(prop-2-enyl)amino]propanoate
• CAS: 847899-95-0
• 化学式: C₁₀H₁₇NO₂
• 分子量: 183.25
• InChiKey: IVVQHXVJZTURIL-VIFPVBQESA-N

物化性质

• 沸点：
  220.4±28.0 °C(Predicted)
• 密度：
  0.940±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (S)-2-(diallylamino)propanoate 在 sodium hydroxide 、 氯化亚砜 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 6.0h， 生成 (S)-2-Diallylamino-propionyl chloride
  参考文献：
  名称：

  Stereoselective intramolecular cycloadditions of homochiral nitrilimines as a source of enantiopure 2,3,3a,4,5,6-hexahydro-pyrrolo[3,4-c]pyrazoles

  摘要：

  Starting from the methyl esters of glycine, L-alanine.. L-phenylalanine and (S)-2-phenylglycine, we developed a synthetic route to the title compounds in the enantiopure form by means of a stereoselective intramolecular 1,3-dipolar cycloaddition of homochiral nitrilimines 5a-d. Fair to good overall product yields and high cycloaddition diastereoselectivity were obtained. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.02.018
• 作为产物：
  描述：

  L-丙氨酸甲酯盐酸盐 、 3-溴丙烯 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以50%的产率得到methyl (S)-2-(diallylamino)propanoate
  参考文献：
  名称：

  刘易斯酸介导的烯丙基胺的不对称[2,3]-σ重排。范围和机制调查

  摘要：

  通过用对映体纯的二氮杂硼烷胺对胺进行季铵化并随后用Et 3 N处理，已实现了非手性烯丙基胺的第一个不对称[2,3]-σ重排。观察到的非对映体和对映体选择性通过调用动力学控制过程得以合理化，并且通过手性路易斯酸-底物复合物的NMR光谱研究获得了对该模型的支持。通过X射线晶体学分析建立了路易斯酸产物配合物的结构，并支持了所提出的机理。

  DOI：

  10.1021/jo062178v

文献信息

• Lewis Acid Assisted Ring-Closing Metathesis of Chiral Diallylamines:  An Efficient Approach to Enantiopure Pyrrolidine Derivatives
  作者：Qian Yang、Wen-Jing Xiao、Zhengkun Yu

  DOI：10.1021/ol047356q

  日期：2005.3.1

  Lewis acid assisted ring-closing olefin metathesis (RCM) of chiral diallylamines, using the second generation RCM ruthenium-based catalyst, leads to enantiopure pyrrolidine derivatives in 79-93% yields under very mild conditions. The scope of the olefin metathesis has been expanded.
• Microwave-assisted ring-closing metathesis of diallylamines: a rapid synthesis of pyrrole and pyrroline derivatives
  作者：Qian Yang、Xin-Yong Li、Hong Wu、Wen-Jing Xiao

  DOI：10.1016/j.tetlet.2006.03.164

  日期：2006.6

  The ring-closing metathesis (RCM) reactions of diallylamines occurred under controlled microwave irradiation. In addition to the high reaction rate, the key features of the reaction are that it can be carried out without deactivation of the substrates and without the use of Lewis acids. (c) 2006 Elsevier Ltd. All rights reserved.
• Lewis Acid Mediated Asymmetric [2,3]-Sigmatropic Rearrangement of Allylic Amines. Scope and Mechanistic Investigation
  作者：Jan Blid、Olaf Panknin、Pavel Tuzina、Peter Somfai

  DOI：10.1021/jo062178v

  日期：2007.2.1

  The first asymmetric [2,3]-sigmatropic rearrangement of achiral allylic amines has been realized by quaternization of the amines with an enantiomerically pure diazaborolidine and subsequent treatment with Et3N. The resultant homoallylic amines were obtained in good yields and excellent ee's. The observed diastereo- and enantioselectivities were rationalized by invoking a kinetically controlled process

  通过用对映体纯的二氮杂硼烷胺对胺进行季铵化并随后用Et 3 N处理，已实现了非手性烯丙基胺的第一个不对称[2,3]-σ重排。观察到的非对映体和对映体选择性通过调用动力学控制过程得以合理化，并且通过手性路易斯酸-底物复合物的NMR光谱研究获得了对该模型的支持。通过X射线晶体学分析建立了路易斯酸产物配合物的结构，并支持了所提出的机理。
• Stereoselective intramolecular cycloadditions of homochiral nitrilimines as a source of enantiopure 2,3,3a,4,5,6-hexahydro-pyrrolo[3,4-c]pyrazoles
  作者：Lara De Benassuti、Paola Del Buttero、Giorgio Molteni

  DOI：10.1016/j.tetasy.2006.02.018

  日期：2006.3

  Starting from the methyl esters of glycine, L-alanine.. L-phenylalanine and (S)-2-phenylglycine, we developed a synthetic route to the title compounds in the enantiopure form by means of a stereoselective intramolecular 1,3-dipolar cycloaddition of homochiral nitrilimines 5a-d. Fair to good overall product yields and high cycloaddition diastereoselectivity were obtained. (c) 2006 Elsevier Ltd. All rights reserved.