methyl (L)-3-phenyllactate triflate | 84028-86-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: methyl (L)-3-phenyllactate triflate
• 英文别名: (S)-3-Phenyl-2-(trifluormethylsulfonyloxy)propionsaeure-methylester；methyl (2S)-3-phenyl-2-(trifluoromethylsulfonyloxy)propanoate
• CAS: 84028-86-4
• 化学式: C₁₁H₁₁F₃O₅S
• 分子量: 312.267
• InChiKey: XFMNYRKEHCMITR-VIFPVBQESA-N

物化性质

• 沸点：
  348.0±42.0 °C(Predicted)
• 密度：
  1.423±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl (L)-3-phenyllactate triflate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 (R)-N-benzyl-phenylalanine
  参考文献：
  名称：

  Effenberger, Franz; Burkard, Ulrike; Willfahrt, Joachim, Liebigs Annalen der Chemie, 1986, # 2, p. 314 - 333

  摘要：

  DOI：
• 作为产物：
  描述：

  L-苯基乳酸甲酯 生成 methyl (L)-3-phenyllactate triflate
  参考文献：
  名称：

  FEENSTRA, R. W.;STOKKINGREEF, E. H. M.;NIVARD, R. J. F.;OTTENHEIJM, H. C.+, TETRAHEDRON, 44,(1988) N 17, C. 5583-5595

  摘要：

  DOI：

文献信息

• Interconversion of (R) and (S)-α-hydroxy esters: precursors of (S) and (R)-o-benzyl-α-hydroxylamino acid esters of high optical purity
  作者：R.W. Feenstra、E.H.M. Stokkingreef、R.J.F. Nivard、H.C.J. Ottenheijm

  DOI：10.1016/s0040-4020(01)86063-4

  日期：1988.1

  (R)- and (S)-α-hydroxy esters 5 are interconverted via their triflates 6 in high chemical as well as optical yields by reaction with dimethylformamide. The same triflates are efficiently converted into N-hydroxy-α-amino acid derivatives 7 of high optical purity.

  （R）-和（S）-α-羟基酯5通过它们的三氟甲磺酸酯6与二甲基甲酰胺反应以高化学产率和光学产率被转化。相同的三氟甲磺酸酯被有效地转化为高光学纯度的N-羟基-α-氨基酸衍生物7。
• An expedient and short synthesis of chiral α-hydrazinoesters: synthesis and conformational analysis of 1:1 [α/α-Nα-hydrazino]mers
  作者：Ralph-Olivier Moussodia、Samir Acherar、Andrea Bordessa、Régis Vanderesse、Brigitte Jamart-Grégoire

  DOI：10.1016/j.tet.2012.04.018

  日期：2012.6

  Different α-hydrazinoesters with high optical purity have been obtained in large scale via an SN2 protocol. A coupling reaction with a natural amino acid leads to the corresponding dimers, which have been oligomerized in order to obtain the 1:1 [α/α-Nα-hydrazino]mer series. Conformational studies show that these mixed oligomers are self-organized in solution via a succession of γ-turn and hydrazinoturn

  经由S N 2协议已大规模获得具有高光学纯度的不同α-肼基酯。1 [α/α-：具有天然氨基酸通向相应二聚体，已经在为了得到1被低聚甲偶联反应Ñ α -肼基]聚体系列。构象研究表明，无论手性碳的绝对构型如何，这些混合的低聚物都是通过连续的γ转变和肼基转变在溶液中自组织的。
• A new chiral alkylation methodology for the synthesis of 2-alkyl-4-ketoacids in high optical purity using 2-triflyloxy esters
  作者：Robert V. Hoffman、Hwa-Ok Kim

  DOI：10.1016/s0040-4039(00)60343-x

  日期：1993.3

  Optical active 2-triflyloxy esters are excellent alkylating agents for β-ketoester enolates. Decarboxylation of the alkylation products gives 2-substituted-4-ketoacid derivatives in high optical purities.

  光学活性的2-三氟乙氧基酯是β-酮酸酯烯酸酯的优异烷基化剂。烷基化产物的脱羧得到高光学纯度的2-取代的4-酮酸衍生物。
• Constraining the amide bond in N-Sulfonylated dipeptide VLA-4 antagonists
  作者：Linda L. Chang、Ginger X. Yang、Ermengilda McCauley、Richard A. Mumford、John A. Schmidt、William K. Hagmann

  DOI：10.1016/j.bmcl.2008.01.045

  日期：2008.3

  The integrin VLA-4 is implicated in several inflammatory disease states. In search of non-peptidic antagonists of VLA-4, rotational constraints were imposed on the amide bond of prototypical N-sulfonylated dipeptide VLA-4 antagonists. By judicious structural modi. cation of the side chains, trisubstituted imidazoles with moderate binding potencies were obtained, for example, 19, VLA-4 IC50 = 237 nM. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis of dibenzyl iminodiacetic derivatives as potential inhibitors of HIV-1 aspartyl protease
  作者：Cécile Abalain、Michel Langlois

  DOI：10.1016/s0223-5234(98)80041-x

  日期：1998.2