(Z)-methyl 2-((tert-butoxycarbonyl)amino)-3-(naphthalen-2-yl)acrylate | 176794-85-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (Z)-methyl 2-((tert-butoxycarbonyl)amino)-3-(naphthalen-2-yl)acrylate
• 英文别名: methyl 2-acetamido-3-(2-naphthyl)propenoate；methyl (Z)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-naphthalen-2-ylprop-2-enoate
• CAS: 176794-85-7
• 化学式: C₁₉H₂₁NO₄
• 分子量: 327.38
• InChiKey: GREHWXHDWKRSQR-VBKFSLOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.88
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  64.63
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (Z)-methyl 2-((tert-butoxycarbonyl)amino)-3-(naphthalen-2-yl)acrylate 在 bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate (R)-N-diphenylphosphino-N-methyl-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethylamine 、 氢气 作用下， 以 四氢呋喃 为溶剂， 25.0 ℃ 、68.95 kPa 条件下， 反应 6.0h， 生成 (S)-2-叔丁氧基羰基氨基-3-萘-2-基-丙酸甲酯
  参考文献：
  名称：

  Synthesis and Application of Phosphinoferrocenylaminophosphine Ligands for Asymmetric Catalysis

  摘要：

  [GRAPHICS]A new class of bidentate ligands utilizing a phosphine-aminophosphine structure has been prepared on a ferrocenylethyl backbone in a straightforward and scalable fashion from acetylferrocene. The unique property of the alpha-ferrocenyl carbonium ion that allows the replacement of a variety of "leaving groups" with retention of configuration greatly facilitates the synthesis, and a number of ligands have been prepared by varying the nitrogen and phosphorus substituents on the aminophosphine. These readily prepared phosphinoferrocenylaminophosphines, known as BoPhoz ligands, show surprising hydrolytic and air stability, with no degradation after 3 years open to the air. The rhodium complexes of these ligands show exceedingly high enantioselectivities (generally >95% ee) and activities often in excess of 50 000 catalyst turnovers per hour for the asymmetric hydrogenation of a wide variety of dehydro-alpha-amino acid and itaconic acid derivatives. They also show high activity and good to excellent enantioselectivity for the hydrogenation of a number of alpha-ketoesters.

  DOI：

  10.1021/jo048312y
• 作为产物：
  描述：

  trimethyl 2-(tert-butoxycarbonylamino)phosphonoacetate 、 2-萘甲醛 在 base 作用下， 生成 (Z)-methyl 2-((tert-butoxycarbonyl)amino)-3-(naphthalen-2-yl)acrylate
  参考文献：
  名称：

  DuPHOS-Rh催化加氢不对称合成β-氨基醇和1,2-二胺

  摘要：

  报道了一种新颖的β-氨基醇和1,2-二胺对映选择性合成方法，该方法结合了对脱氢-β-氨基醇和脱氢-α-氨基醛肟的不对称氢化的首次描述。

  DOI：

  10.1016/s0040-4039(99)01376-3

文献信息

• Asymmetric Synthesis of β,β-Disubstituted Alanines via a Sequential C(sp2)–C(sp3) Cross-Coupling–Hydrogenation Strategy
  作者：David A. Petrone、Jonathan Maturano、James Herbort、Erin E. Plasek、J. Mayeli Vivaldo-Nikitovic、David Sarlah

  DOI：10.1021/acs.orglett.4c02376

  日期：2024.7.26

  allows access to a diverse array of valuable β,β-disubstituted alanine derivatives. This synthesis exhibits broad functional group tolerance, and permits efficient access to β-aryl-β-alkyl, and the more rarely reported β,β-dialkyl Ala derivatives with high yield and excellent enantioselectivity. This transformation has been exhibited on decagram quantity, and can be used to generate Fmoc amino acid derivatives

  我们报告了连续 C(SP 2 )–C(SP 3 ) Suzuki 交叉偶联不对称氢化策略的开发，该策略允许获得多种有价值的 β,β-二取代丙氨酸衍生物。该合成表现出广泛的官能团耐受性，并可以有效地获得β-芳基-β-烷基和更罕见报道的β,β-二烷基Ala衍生物，具有高产率和优异的对映选择性。这种转化已在十克数量上得到展示，并且可用于生成可用于 SPPS 的 Fmoc 氨基酸衍生物。
• Solvent-free synthesis of unsaturated amino esters in a ball-mill
  作者：Alice Baron、Jean Martinez、Frédéric Lamaty

  DOI：10.1016/j.tetlet.2010.09.069

  日期：2010.12

  The ball-milling technique was used under solvent-free conditions to perform a Horner-Wadsworth-Emmons reaction in the presence of a mild carbonate base. Starting from a phosphonate-substituted glycine, this method gave access to Boc-protected unsaturated amino esters in excellent yield and selectivity in many cases. The scope of the reaction was delineated. (C) 2010 Elsevier Ltd. All rights reserved.
• Copper-Catalyzed Asymmetric Hydroboration of α-Dehydroamino Acid Derivatives: Facile Synthesis of Chiral β-Hydroxy-α-amino Acids
  作者：Zhi-Tao He、Yi-Shuang Zhao、Ping Tian、Chuan-Chuan Wang、Han-Qing Dong、Guo-Qiang Lin

  DOI：10.1021/ol500219e

  日期：2014.3.7

  The Cu-catalyzed asymmetric conjugate hydroboration reaction of beta-substituted alpha-dehydroamino acid derivatives has been established, affording enantioenriched syn- and anti-beta-boronate-alpha-amino acid derivatives with excellent combined yields (83-99%, dr approximate to 1:1) and excellent enantioselectivities (92-98% ee). The hydroboration products were expediently converted into valuable beta-hydroxy-alpha-amino acid derivatives, which were widely used in the preparation of chiral drugs and bioactive molecules.