N-allylated phenylalanine methyl ester | 73270-67-4

• 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-allylated phenylalanine methyl ester
• 英文别名: (S)-2-allylamino-3-phenyl-propionic acid methyl ester；methyl (2S)-3-phenyl-2-(prop-2-enylamino)propanoate
• CAS: 73270-67-4
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: AVFUMAMUDZCOOO-LBPRGKRZSA-N

物化性质

• 沸点：
  316.0±30.0 °C(Predicted)
• 密度：
  1.031±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-allylated phenylalanine methyl ester 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 生成 (S)-N-allyl-N-(1-hydroxy-3-phenylpropan-2-yl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  I₂-Mediated Diversity Oriented Diastereoselective Synthesis of Amino Acid Derived trans-2,5-Disubstituted Morpholines, Piperazines, and Thiomorpholines

  摘要：

  Diastereoselective trans-2,5-disubstituted amino acids derived diverse morpholines, piperazines and thiomorpholines were prepared in 30 min-1 h with high yields through iodine-mediated 6-exotrig type cyclization from a single common synthetic intermediate. The displacement of iodine with hydride ion gave a methyl substituent at the 2-position of morpholines which provides an additional opportunity for diversity oriented nucleophilic substitution on the rings as well as incorporation of substituents at the 5-position from amino acids constituents.

  DOI：

  10.1021/co200129t
• 作为产物：
  描述：

  L-苯丙氨酸甲酯盐酸盐 在 lithium hydroxide 、 potassium carbonate 、 巯基乙酸 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 N-allylated phenylalanine methyl ester
  参考文献：
  名称：

  Microwave-accelerated cross-metathesis reactions of N-allyl amino acid substrates

  摘要：

  Microwave heating has been utilised for the cross-metathesis reaction of N-allyl amino acid substrates to generate olefin homodimers. Remarkable acceleration of the cross-metathesis reaction (minutes compared to hours) over conventional reflux heating was observed. In addition, improved reaction yields and similar E/Z ratios for the cross-metathesis products were achieved. (c) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2005.08.126

文献信息

• Conformationally Constrained Substance P Analogues:  The Total Synthesis of a Constrained Peptidomimetic for the Phe⁷-Phe⁸ Region
  作者：Yunsong Tong、Yvette M. Fobian、Meiye Wu、Norman D. Boyd、Kevin D. Moeller

  DOI：10.1021/jo991649t

  日期：2000.4.1

  substance P analogue with the use of solid-phase peptide synthesis. A similar intramolecular reductive amination strategy was used to synthesize a substance P analogue having only Phe7 constrained, and the original 3-phenylproline was converted into a substance P analogue having only Phe8 constrained. All of the analogues were examined for their ability to displace substance P from its NK-1 receptor

  已经合成了用于物质P的Phe7-Phe8区的内酰胺基拟肽。该合成使用阳极酰胺氧化来选择性官能化3-苯基脯氨酸衍生物的C5位。所得的脯氨酸衍生物与Cbz保护的苯丙氨酸偶联，并使用分子内还原胺化策略将偶联的材料转化为双环哌嗪酮环骨架。最终结果是二肽构件，将物质P的Phe7-Phe8区的两个拟议的受体结合构型之一嵌入双环骨架中。然后使用固相肽合成将构件转换为受限物质P类似物。使用类似的分子内还原胺化策略合成仅具有Phe7约束的P物质类似物，并且将原始的3-苯基脯氨酸转化为仅具有Phe8约束的P物质类似物。检查所有类似物从其NK-1受体置换P物质的能力。
• OLIGOOXOPIPERAZINES AND METHODS OF MAKING AND USING THEM
  申请人：Arora Paramjit S.

  公开号：US20120040992A1

  公开（公告）日：2012-02-16

  The present invention relates to oligooxopiperazines and their use. Methods for preparing oligooxopiperazines are also disclosed.

  本发明涉及寡氧代哌嗪及其用途。还公开了制备寡氧代哌嗪的方法。
• LiOH-mediated N-monoalkylation of α-amino acid esters and a dipeptide ester using activated alkyl bromides
  作者：Jong Hyun Cho、B.Moon Kim

  DOI：10.1016/s0040-4039(01)02394-2

  日期：2002.2

  Selective N-monoalkylation of α-amino esters with activated alkyl bromides was studied using various alkali or alkali earth metal bases. In the production of N-monoalkylated amino ester derivatives and suppression of N,N-dialkylation, lithium hydroxide was more effective than any other alkali or alkali earth bases examined. Using this protocol, a variety of N-alkylated α-amino esters and even dipeptide

  使用各种碱金属或碱土金属碱，研究了用活化的烷基溴对α-氨基酯的选择性N-单烷基化。在N-单烷基化氨基酯衍生物的生产和N，N-二烷基化的抑制中，氢氧化锂比任何其他所检查的碱金属或碱土金属碱更有效。使用该方案，已经使用各种活化的烷基溴成功地制备了各种N-烷基化的α-氨基酯，甚至二肽酯。
• Synthesis of cyclic sulfamoyl carbamates and ureas via ring-closing metathesis
  作者：Joseph M. Dougherty、María Jiménez、Paul R. Hanson

  DOI：10.1016/j.tet.2005.03.140

  日期：2005.6

  Synthetic routes to a diverse set of cyclic sulfamoyl carbamates and ureas are reported. These routes utilize 3-component coupling, Mitsunobu alkylation, and ring-closing metathesis using the second-generation Grubbs catalyst to achieve the synthesis of the target S-heterocyclic compounds. Cyclic S-heterocycles ranging from 9- to 11-membered rings have been obtained.

  据报道，合成途径可形成多种环状氨基甲酸酯氨基甲酸酯和脲。这些途径利用三组分偶联，Mitsunobu烷基化和使用第二代Grubbs催化剂的闭环复分解反应来实现目标S杂环化合物的合成。已经获得了9至11元环的环状S-杂环。
• Efficient Method for the Synthesis of Chiral Pyrrolidine Derivatives via Ring-Closing Enyne Metathesis Reaction
  作者：Qian Yang、Howard Alper、Wen-Jing Xiao

  DOI：10.1021/ol062959i

  日期：2007.3.1

  [reaction: see text] A series of new pyrrolidine derivatives were prepared directly in very good yields, from the substrates containing a basic or nucleophilic N atom via ring-closing enyne metathesis reaction under mild reaction conditions. Moreover, the reaction occurs smoothly without the presence of ethylene gas.

  [反应：见正文]在温和的反应条件下，通过闭环烯炔复分解反应，从含有碱性或亲核N原子的底物中直接以很高的收率制备了一系列新的吡咯烷衍生物。此外，反应在没有乙烯气体存在的情况下平稳进行。