N,N-bis-allyl-L-phenylalanine methyl ester | 79561-72-1

• 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: N,N-bis-allyl-L-phenylalanine methyl ester
• 英文别名: methyl 2-(diallylamino)-3-phenylpropanoate；methyl 2-diallylamino-3-phenylpropionate；N,N-diallyl-L-phe-OMe；methyl (2S)-2-[bis(prop-2-enyl)amino]-3-phenylpropanoate
• CAS: 79561-72-1
• 化学式: C₁₆H₂₁NO₂
• 分子量: 259.348
• InChiKey: XUGOCZJBLUWFHR-HNNXBMFYSA-N

物化性质

• 沸点：
  345.8±42.0 °C(Predicted)
• 密度：
  1.014±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  N,N-bis-allyl-L-phenylalanine methyl ester 在 Wilkinson's catalyst 作用下， 以 水 、 乙腈 为溶剂， 反应 2.0h， 以76%的产率得到L-苯丙氨酸甲酯
  参考文献：
  名称：

  胺的新保护基。由L-酪氨酸合成抗衣壳蛋白

  摘要：

  描述了伯胺和α-氨基酸的酸和碱稳定的，耐亲核试剂的保护基，该保护基已用于标题化合物的合成中。

  DOI：

  10.1016/s0040-4039(01)90356-9
• 作为产物：
  描述：

  L-苯丙氨酸甲酯 、 3-溴丙烯 在 N,N-二异丙基乙胺 作用下， 以 甲苯 为溶剂， 反应 1.5h， 以75%的产率得到N,N-bis-allyl-L-phenylalanine methyl ester
  参考文献：
  名称：

  胺的新保护基。由L-酪氨酸合成抗衣壳蛋白

  摘要：

  描述了伯胺和α-氨基酸的酸和碱稳定的，耐亲核试剂的保护基，该保护基已用于标题化合物的合成中。

  DOI：

  10.1016/s0040-4039(01)90356-9

文献信息

• Role of the <i>g</i><i>em</i>-Difluoro Moiety in the Tandem Ring-Closing Metathesis−Olefin Isomerization:  Regioselective Preparation of Unsaturated Lactams
  作者：Santos Fustero、María Sánchez-Roselló、Diego Jiménez、Juan F. Sanz-Cervera、Carlos del Pozo、José Luis Aceña

  DOI：10.1021/jo0525635

  日期：2006.3.31

  Careful selection of the metathesis catalyst, solvent, and reaction conditions allows for the efficient and regioselective synthesis of isomeric fluorinated and nonfluorinated lactam derivatives II and III from precursor amides I through a ring-closing metathesis (RCM) reaction or a tandem RCM−isomerization protocol, respectively. The presence of the gem-difluoro moiety in the starting materials exerts

  仔细选择复分解催化剂，溶剂和反应条件，可以通过闭环复分解（RCM）反应或串联RCM异构化协议从前体酰胺I高效且区域选择性地合成异构的氟化和非氟化内酰胺衍生物II和III。， 分别。起始物中的宝石-二氟部分的存在通过指导异构化步骤发挥关键作用，从而使整体串联转化成为区域选择性过程。还讨论了该协议的范围，局限性和综合实用性。
• Synthesis of Fluoroalkylated Pyrrolidines through Neat Reaction of Fluoroalkyl Iodides with <i>N, N</i> ‐Diallylamines
  作者：Ting Mao、Weipiao Li、Xiao‐Xiao Liu、Haoyang Wang、Wen‐Yong Han、Jie Tong、Shi‐Ji Xiao、Liang Zhao、Chun‐Yang He

  DOI：10.1002/adsc.202300092

  日期：——

  We presented a cascade transformation of N, N-diallylamines and fluoroalkyl iodides into various functionalized fluoroalkylated pyrrolidines through a visible light-induced synthetic process in the solvent-free conditions. In this reaction system, the substrate N, N-diallylamine acted both as the base and the electron donor. We further demonstrated the practicality of this protocol by the direct modification

  我们提出了在无溶剂条件下通过可见光诱导合成过程将N , N-二烯丙基胺和氟烷基碘化物级联转化为各种功能化氟烷基化吡咯烷。在该反应体系中，底物N,N-二烯丙胺既充当碱基又充当电子供体。我们通过氨基酸和药物分子的直接修饰进一步证明了该方案的实用性。
• 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.
• Synthesis of enantiomerically pure (+)- and (−)-protected 5-aminomethyl-1,3-oxazolidin-2-one derivatives from allylamine and carbon dioxide
  作者：Isabelle Fernández、Luis Muñoz

  DOI：10.1016/j.tetasy.2006.08.006

  日期：2006.10

  The stereoselective synthesis of enantiomerically pure (5R)- and (5S)-aminomethyl-oxazolidinones with different protecting groups have been carried out from an allyl amine as the source of the carbon backbone. The key reaction is the high yield iodiocyclization of enantiomerically pure allylphenethyl amine in the presence of carbon dioxide. (c) 2006 Elsevier Ltd. All rights reserved.
• 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.