tert-butyl (5-methoxyfuran-2-yl)(phenyl)methylcarbamate | 779342-73-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl (5-methoxyfuran-2-yl)(phenyl)methylcarbamate
• 英文别名: tert-butyl N-[(R)-(5-methoxyfuran-2-yl)-phenylmethyl]carbamate
• CAS: 779342-73-3
• 化学式: C₁₇H₂₁NO₄
• 分子量: 303.358
• InChiKey: UUIGAMVHWHTJIF-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  60.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (5-methoxyfuran-2-yl)(phenyl)methylcarbamate 在 N-溴代丁二酰亚胺(NBS) 、 碳酸氢钠 作用下， 以 乙醚 为溶剂， 以90%的产率得到tert-butyl (Z)-4-(methoxycarbonyl)-2-oxo-1-phenylbut-3-enylcarbamate
  参考文献：
  名称：

  Organocatalytic Asymmetric Aza-Friedel−Crafts Alkylation of Furan

  摘要：

  A new asymmetric entry of the 1,2-aza-Friedel-Crafts reaction catalyzed by a chiral phosphoric acid is described. The present reaction has provided an atom-economical route to furan-2-ylamine derivatives in a highly enantioselective fashion. The synthetic utility of these products was displayed by oxidative cleavage of the furan ring (aza-Achmatowicz reaction) to form a 1,4-dicarbonyl compound that could be further derivatized to a chiral gamma-butenolid.

  DOI：

  10.1021/ja046185h
• 作为产物：
  描述：

  2-呋甲醚 、 benzaldehyde N-boc imine 在 2,6-bis(2,4,6,2'',4'',6''-hexamethyl-[1,1';3',1'']terphenyl-5'-yl)-4-oxo-3,5-dioxa-4λ⁵-phosphacyclohepta[2,1-a;3,4-a']dinaphthalen-4-ol 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以78%的产率得到tert-butyl (5-methoxyfuran-2-yl)(phenyl)methylcarbamate
  参考文献：
  名称：

  Metal-Free Chiral Phosphoric Acid or Chiral Metal Phosphate as Active Catalyst in the Activation of N-Acyl Aldimines

  摘要：

  在三种反应中确认了无金属手性磷酸或手性金属磷酸作为活性催化剂的作用。在 aza-Friedel-Crafts 和 aza-ene 型反应中，无金属手性磷酸（即手性 Brønsted 酸）被验证为活性催化剂。相反，α-二氮乙酸与醛亚胺的取代反应则是由含盐的手性磷酸加速的，因此手性金属磷酸很可能作为活性催化剂发挥作用。

  DOI：

  10.1055/s-0030-1260545

文献信息

• Process for production of amines
  申请人：Terada Masahiro

  公开号：US20070142639A1

  公开（公告）日：2007-06-21

  A process for producing an amine which is characterized by reacting an imine with a nucleophilic compound (except a trialkylsilyl vinyl ether) in the presence of a phosphoric acid derivative represented by the formula (1): wherein A 1 represents a spacer; X 1 and X 2 represent each independently a divalent nonmetal atom or a divalent nonmetal atomic group; and Y 1 is oxygen or sulfur. The invention provides a process by which amines (particularly optically active amines) useful as intermediates of medicines, agricultural chemicals, or the like can be produced without special post-treatment in high yield at high optical purity; and phosphoric acid derivatives (particularly optically active phosphoric acid derivatives) useful in the production of the amines.

  一种生产胺的方法，其特征在于在式（1）所代表的磷酸衍生物存在下，将亚胺与一种亲核化合物（三烷基硅基乙烯醚除外）反应： 其中A1代表一个间隔物；X1和X2分别独立表示二价非金属原子或二价非金属原子团；Y1为氧或硫。该发明提供了一种方法，通过该方法，可以在高光学纯度下高产率地生产用作药品、农药等中间体的胺（特别是光学活性胺），而无需进行特殊的后处理；以及用于生产这些胺的磷酸衍生物（特别是光学活性磷酸衍生物）。
• BIS-PHOSPHATE COMPOUND AND ASYMMETRIC REACTION USING THE SAME
  申请人：Terada Masahiro

  公开号：US20120330038A1

  公开（公告）日：2012-12-27

  A novel bis-phosphate compound is provided which can be applied to a wide range of reactive substrates and reactions as an asymmetric reaction catalyst and can realize an asymmetric reaction affording a high yield and a high enantiomeric excess. The bis-phosphate compound has a tetraaryl skeleton represented by General Formula (1). In an asymmetric reaction, an amidodiene and an unsaturated aldehyde compound are reacted with each other in the presence of the optically active bis-phosphate compound to give an optically active amidoaldehyde. The invention allows a reaction such as an asymmetric Diels-Alder reaction to proceed efficiently, which has been difficult with conventional mono-phosphate compounds. Thus, the invention enables an industrially feasible method for the production of optically active amidoaldehydes, optically active β-amino acid derivatives, optically active diamine compounds, optically active pyrrolidine derivatives and optically active dihydropyran derivatives which are useful as products such as medicines, agricultural chemicals and chemical products as well as synthesis intermediates for such products.

  提供了一种新型的双磷酸盐化合物，可应用于广泛的反应底物和反应作为不对称反应催化剂，并且可以实现产率高和对映体过量高的不对称反应。该双磷酸盐化合物具有由通用式（1）表示的四芳基骨架。在不对称反应中，存在光学活性的双磷酸盐化合物的情况下，通过使酰胺二烯和不饱和醛化合物相互反应，得到光学活性的酰胺醛。该发明使得像不对称Diels-Alder反应这样的反应能够高效进行，而传统的单磷酸盐化合物很难实现。因此，该发明实现了一种工业上可行的方法，用于生产用作药品、农药和化工产品以及用于这些产品的合成中间体的光学活性酰胺醛、光学活性β-氨基酸衍生物、光学活性二胺化合物、光学活性吡咯烷衍生物和光学活性二氢吡喃衍生物。
• Organocatalytic Asymmetric Aza-Friedel−Crafts Alkylation of Furan
  作者：Daisuke Uraguchi、Keiichi Sorimachi、Masahiro Terada

  DOI：10.1021/ja046185h

  日期：2004.9.1

  A new asymmetric entry of the 1,2-aza-Friedel-Crafts reaction catalyzed by a chiral phosphoric acid is described. The present reaction has provided an atom-economical route to furan-2-ylamine derivatives in a highly enantioselective fashion. The synthetic utility of these products was displayed by oxidative cleavage of the furan ring (aza-Achmatowicz reaction) to form a 1,4-dicarbonyl compound that could be further derivatized to a chiral gamma-butenolid.
• Metal-Free Chiral Phosphoric Acid or Chiral Metal Phosphate as Active Catalyst in the Activation of N-Acyl Aldimines
  作者：Masahiro Terada、Kyohei Kanomata

  DOI：10.1055/s-0030-1260545

  日期：2011.6

  Whether metal-free chiral phosphoric acid or chiral metal phosphate functions as an active catalyst was confirmed in three reactions. In the aza-Friedel-Crafts and aza-ene-type reactions, a metal-free chiral phosphoric acid, namely, a chiral Brønsted acid, was verified to be the active catalyst. In contrast, the substitution ­reaction of α-diazoacetate with aldimine was accelerated by a salt-containing chiral phosphoric acid and hence chiral metal phosphate presumably functioned as an active catalyst.

  在三种反应中确认了无金属手性磷酸或手性金属磷酸作为活性催化剂的作用。在 aza-Friedel-Crafts 和 aza-ene 型反应中，无金属手性磷酸（即手性 Brønsted 酸）被验证为活性催化剂。相反，α-二氮乙酸与醛亚胺的取代反应则是由含盐的手性磷酸加速的，因此手性金属磷酸很可能作为活性催化剂发挥作用。