2-acetylaminocyclopent-1-enecarboxylic acid ethyl ester | 29942-18-5

• 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: 2-acetylaminocyclopent-1-enecarboxylic acid ethyl ester
• 英文别名: ethyl 2-acetamido-1-cyclopentene-1-carboxylate；2-acetylamino-cyclopent-1-enecarboxylic acid ethyl ester；2-Acetylamino-cyclopent-1-encarbonsaeure-aethylester；2-Ethoxycarbonyl-1-acetylaminocyclopenten；Ethyl 2-acetamidocyclopentene-1-carboxylate
• CAS: 29942-18-5
• 化学式: C₁₀H₁₅NO₃
• 分子量: 197.234
• InChiKey: APORVQRUXVOJBR-UHFFFAOYSA-N

物化性质

• 沸点：
  359.4±42.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-acetylaminocyclopent-1-enecarboxylic acid ethyl ester 在 barium dihydroxide 作用下， 生成 cis-hexahydro-cyclopentimidazol-2-one
  参考文献：
  名称：

  Studies in the Cyclopentane Series. I. The Synthesis of 1,2-Ureylenecyclopentane and Related Compounds

  摘要：

  DOI：

  10.1021/ja01150a023
• 作为产物：
  描述：

  2-氧代环戊羧酸乙酯 在 ammonium acetate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 4.0h， 生成 2-acetylaminocyclopent-1-enecarboxylic acid ethyl ester
  参考文献：
  名称：

  Development of a Suitable Process for the Preparation of a TNF-α Converting Enzyme Inhibitor, WAY-281418

  摘要：

  A suitable process for the preparation of kilogram quantities of a TNF-alpha converting enzyme (TACE) inhibitor (WAY-281418) was developed using isatin 13 as starting material and an efficient coupling step for the formation of sulfonamide 8 in a 15% overall yield. Process preparation of (+)-(1S,2R)-2-aminocyclopentane-1-carboxylic acid (7, (+)-cispentacin), a chiral component for WAY-281418, was successfully scaled up via an asymmetric hydrogenation reaction. Crystallization allowed the isolation of all intermediates and the final product 9.

  DOI：

  10.1021/op800090s

文献信息

• C1-symmetric bisphosphine ligands and their use in the asymmetric synthesis of pregabalin
  申请人：Bao Jian

  公开号：US20050228190A1

  公开（公告）日：2005-10-13

  Materials and methods for preparing (S)-(+)-3-(aminomethyl)-5-methyl-hexanoic acid and structurally related compounds via enantioselective hydrogenation of prochiral olefins are disclosed. The methods employ novel chiral catalysts, which include C 1 -symmetric bisphosphine ligands bound to transition metals.

  通过对原生手性烯烃进行对映选择性加氢制备(S)-(+)-3-(氨甲基)-5-甲基己酸及其结构相关化合物的材料和方法已被披露。这些方法采用了新颖的手性催化剂，其中包括与过渡金属结合的C1对称双膦配体。
• Enantioselective Hydrogenation of Tetrasubstituted Olefins of Cyclic β-(Acylamino)acrylates
  作者：Wenjun Tang、Shulin Wu、Xumu Zhang

  DOI：10.1021/ja035777h

  日期：2003.8.1

  Hydrogenation of a series of cyclic beta-(acylamino)acrylates with tetrasubstituted olefins has been accomplished successfully with the use of Ru catalysts with chiral biaryl ligands such as C3-TunaPhos, and up to over 99% ee's have been achieved. This methodology provides an efficient catalytic method for the synthesis of both cis and trans chiral cyclic beta-amino acid derivatives.

  使用具有手性联芳基配体（如 C3-TunaPhos）的 Ru 催化剂成功地完成了一系列环状 β-（酰氨基）丙烯酸酯与四取代烯烃的氢化，并且已实现高达 99% 以上的 ee。该方法为顺式和反式手性环状β-氨基酸衍生物的合成提供了一种有效的催化方法。
• Preparation of chiral cyclic amino acids and derivatives
  申请人：The Penn State Research Foundation

  公开号：US20040242889A1

  公开（公告）日：2004-12-02

  Cyclic &bgr;-(acylamino)acrylate derivatives were hydrogenated using Ru-chiral phosphine ligand catalysts and thereafter converted to the corresponding cyclic &bgr;-aminoacids in high yield and enantioselectivity according to the reaction scheme: 1

  使用Ru-手性膦配体催化剂对环状&bgr;-(酰胺基)丙烯酸酯衍生物进行氢化反应，然后根据反应方案将其转化为相应的环状&bgr;-氨基酸，收率和对映选择性均很高。1
• Highly Enantioselective Asymmetric Hydrogenation of β-Acetamido Dehydroamino Acid Derivatives Using a Three-Hindered Quadrant Rhodium Catalyst
  作者：He-Ping Wu、Garrett Hoge

  DOI：10.1021/ol048386w

  日期：2004.9.1

  reported three-hindered quadrant chiral ligand and its corresponding rhodium complex provide high enantioselectivity for the asymmetric hydrogenation of beta-acetamido dehydroamino acid substrates. Both (E)- and (Z)-substrates are hydrogenated with high enantioselectivity in all of the reported examples. Asymmetric hydrogenation of a cyclic beta-acetamido dehydroamino acid substrate in 85% ee is also reported

  [反应：见正文]先前报道的三阻碍象限手性配体及其相应的铑配合物为β-乙酰氨基脱氢氨基酸底物的不对称氢化提供了高对映选择性。在所有报道的实施例中，（E）-和（Z）-底物都以高对映选择性被氢化。还报道了在85％ee中环状β-乙酰氨基脱氢氨基酸底物的不对称氢化。
• Yakimovich,S.I. et al., Journal of Organic Chemistry USSR (English Translation), 1977, vol. 13, p. 1069 - 1074
  作者：Yakimovich,S.I. et al.

  DOI：——

  日期：——