N-allyl (L)-leucine methyl ester | 73270-65-2

• 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-allyl (L)-leucine methyl ester
• 英文别名: N-allylated leucine methyl ester；methyl N-allyl-L-leucinate；H-(Nall)Leu-OMe；(S)-N-Allyl-Leu-OMe；methyl (2S)-4-methyl-2-(prop-2-enylamino)pentanoate
• CAS: 73270-65-2
• 化学式: C₁₀H₁₉NO₂
• 分子量: 185.266
• InChiKey: WEIWEPKUNKYJCT-VIFPVBQESA-N

物化性质

• 沸点：
  235.9±23.0 °C(Predicted)
• 密度：
  0.918±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 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-allyl (L)-leucine methyl ester 在 吡啶 、 lithium aluminium tetrahydride 、 potassium iodide 作用下， 以 四氢呋喃 为溶剂， 反应 19.0h， 生成 (S)-N-allyl-N-(1-(benzylamino)-4-methylpentan-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-亮氨酸 在 氯化亚砜 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 N-allyl (L)-leucine methyl ester
  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

文献信息

• The Synthesis of Sterically Demanding Amino Acid-Derived Cyclic Phosphonamides
  作者：Kevin T. Sprott、Paul R. Hanson

  DOI：10.1021/jo005545q

  日期：2000.11.1

  4-diamines in the synthesis of amino acid-derived cyclic phosphonamides 1-3 are described. The 1,4-diamines are synthesized via three methods: (i) amino acid/fumaryl chloride coupling followed by amide reduction, (ii) amino acid/1,4-diamine coupling followed by amide reduction, and (iii) a template-supported ring-closing metathesis/hydrolysis sequence. The pseudo C(2)-symmetric cyclic phosphonamides 1-3 are

  描述了C（2）-对称的1,4-二胺在氨基酸衍生的环状膦酰胺1-3的合成中的制备和利用。1,4-二胺是通过三种方法合成的：（i）氨基酸/富马酰氯偶联，然后进行酰胺还原；（ii）氨基酸/ 1,4-二胺偶联，然后进行酰胺还原；以及（iii）模板-支持的闭环复分解/水解序列。通过将C（2）对称的1,4-二胺缩合到P（III）中心，然后进行氧化来制备伪C（2）对称的环状膦酰胺1-3。
• Azabicyclo[3.1.0]hexane-1-ols as frameworks for the asymmetric synthesis of biologically active compounds
  作者：Mouhamad Jida、Régis Guillot、Jean Ollivier

  DOI：10.1016/j.tetlet.2007.10.003

  日期：2007.12

  obtained by Ti(IV)-mediated cyclopropanation of amino acid derivatives, constitute versatile, and unprecedented intermediates for the asymmetric synthesis of pharmacologically active products. Indeed, through selective rearrangement, these compounds undergo unusual ring cleavage to lead to pyrrolidinones. Fe(III)-promoted ring opening followed by basic dehydrohalogenation furnishes optically active dihydropyridinones

  氮杂双环[3.1.0]己烷-1-醇很容易通过Ti（IV）介导的氨基酸衍生物环丙烷化反应获得，它是多用途且空前的中间体，可用于不对称合成药理活性产物。实际上，通过选择性重排，这些化合物经历不寻常的环断裂，从而导致吡咯烷酮。Fe（III）促进的开环，然后进行基本的脱卤化氢，提供了光学活性的二氢吡啶并酮，而Ce（IV）促进的开环则通过自由基过程提供了手性三环哌啶酮。
• 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。
• Convergent and Selective Synthesis of Pyrrolidinones, Piperidinones, Dihydropyridinones and Pyridinols from a Common Intermediate - Potential Precursors of Bioactive Products
  作者：Mouhamad Jida、Jean Ollivier

  DOI：10.1002/ejoc.200800380

  日期：2008.8

  furnish racemic pyrrolidinones as a mixture of diastereomers and piperidinones. In contrast, the synthesis of optically active dihydropyridinones was achieved through a one-pot FeCl3/AcONa reaction or performed by using bis(sym-collidine)iodine hexafluorophosphate. Furthermore, whereas the palladium-mediated hydrogenolysis of these dihydropyridinones furnished both chiral piperidinones and original pyridinols

  钛介导的天然和非天然 β-氨基酸衍生物的环丙烷化提供氮杂双环 [3.1.0] 己-1-醇作为非对映异构体的混合物，可通过硅胶色谱法分离。根据所采用的环裂解程序，这些化合物可有效地产生多种用于合成药物的中间体。因此，根据实验条件，碱性处理可以提供作为非对映异构体和哌啶酮混合物的外消旋吡咯烷酮。相比之下，光学活性二氢吡啶酮的合成是通过一锅 FeCl3/AcONa 反应实现的，或者通过使用双（sym-collidine）碘六氟磷酸盐进行的。此外，虽然钯介导的这些二氢吡啶酮的氢解提供了手性哌啶酮和原始吡啶醇，CeIV 促进的自由基过程产生手性三环哌啶酮。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)