Methyl (Z)-N-acetamidocinnamate | 64590-81-4

• 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: Methyl (Z)-N-acetamidocinnamate
• 英文别名: methyl (E)-2-(acetylamino)-3-phenylpropenoate；(E)-α-(N-acylamino)cinnamic acid methyl ester；methyl (E)-α-(acetamido)cinnamate；methyl (Z)-N-acetylaminocinnamate；α-acetamidocinnamic acid methyl ester；Methyl 2-acetamido-3-phenylacrylate；methyl (Z)-2-(N-acetamido)cinnamate；methyl (Z)-2-(acetylamino)cinnamate；Methyl 2-acetamidocynnamate；(E)-Methyl-α-acetamido-zimtsaeureester；(Z)-methyl 2-acetamido-3-phenylacrylate；methyl trans-acetamidocinnamate；cis-methyl acetamidocinnamate；methyl (e)-2-(N-acetylamino)-3-phenylpropenoate；methyl (E)-2-acetamido-3-phenylprop-2-enoate
• CAS: 64590-81-4
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: USKHBABPFFAKJD-DHZHZOJOSA-N

物化性质

• 沸点：
  427.8±45.0 °C(Predicted)
• 密度：
  1.159±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  Methyl (Z)-N-acetamidocinnamate 在 bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate chiral phosphine-phosphite ligand 、 氢气 作用下， 以 二氯甲烷 为溶剂， 19.85 ℃ 、101.32 kPa 条件下， 反应 3.0h， 生成 N-乙酰基-D-苯基丙氨酸甲酯
  参考文献：
  名称：

  膦-亚磷酸酯，一类用于高活性和对映选择性加氢的新型助剂

  摘要：

  在温和的反应条件下，在 Rh 催化的 α,β-不饱和羧酸衍生物的氢化反应中，具有优异的对映选择性 (ee >99%) 和良好的活性 (TOF >1200 h-1)，第一家族的膦-亚磷酸酯配体含有糖骨架；这些配体优于它们的二膦、二亚磷酸酯和次膦酸酯类似物。

  DOI：

  10.1039/b007850f
• 作为产物：
  描述：

  N-acetamido cinnamic acid 以 甲醇 、 乙醚 为溶剂， 生成 Methyl (Z)-N-acetamidocinnamate
  参考文献：
  名称：

  Asymmetric hydrogenation. Rhodium chiral bisphosphine catalyst

  摘要：

  DOI：

  10.1021/ja00460a018

文献信息

• [EN] IONIC LIQUID SOLVENTS<br/>[FR] SOLVANTS LIQUIDES IONIQUES
  申请人：UNIV DUBLIN CITY

  公开号：WO2010097412A1

  公开（公告）日：2010-09-02

  A chiral ionic compound comprising an alkyl substituted imidazolium or pyridinium cationic core having an alkyl ester side chain (-alkyl-C(O)O-) directly linked to the core and an associated counter anion, characterized in that the -O- atom of the ester side chain is linked to an alpha, a beta or a gamma hydroxycarboxylic acid functionality via the alpha, beta or gamma hydroxy of the acid functionality and the hydroxycarboxylic acid functionality has at least one asymmetric carbon, or characterized in that an -N= atom of the alkyl substituted imidazolium or pyridinium cationic core is substituted with an alpha, a beta or a gamma hydroxy group of a alpha, a beta or a gamma hydroxycarboxylic acid functionality and the hydroxycarboxylic acid functionality has at least one asymmetric carbon. The chiral ionic liquids (CILs) may be used as novel solvents, in particular for organic synthesis. The CILs have the potential to induce asymmetry into substrates or catalysts in a variety of organic transformations. A number of the compounds have low antimicrobial and low antifungal toxicities and are also biodegradable CILs.

  一种手性离子化合物，包括具有烷基取代的咪唑或吡啶阳离子核心，其具有直接连接到核心的烷基酯侧链（-烷基-C（O）O-）和相关的对应阴离子，其特征在于酯侧链的-O-原子通过α、β或γ羟基羧酸功能与羧酸功能的α、β或γ羟基相连，且羟基羧酸功能具有至少一个不对称碳，或者其特征在于烷基取代的咪唑或吡啶阳离子核心的-N=原子被α、β或γ羟基羧酸功能的α、β或γ羟基取代，且羟基羧酸功能具有至少一个不对称碳。这种手性离子液体（CILs）可用作新型溶剂，特别适用于有机合成。这些CILs有潜力在各种有机转化中向底物或催化剂引入不对称性。其中一些化合物具有低抗菌和低抗真菌毒性，并且也是可生物降解的CILs。
• Stereoselective Synthesis of (<i>E</i>)-α,β-Dehydroamino Acid Esters
  作者：Yoko Yasuno、Makoto Hamada、Takeshi Yamada、Tetsuro Shinada、Yasufumi Ohfune

  DOI：10.1002/ejoc.201300112

  日期：2013.4

  Dehydroamino acid (Dhaa) is recognized as a useful tool or substrate for amino acid and peptide research. Although the stereoselective synthesis of the thermodynamically more stable Z-Dhaa has been well examined and established, the stereoselective synthesis of E-Dhaa has still remained to be a challenging synthetic task. In this paper, a stereoselective synthesis of E-Dhaa esters using a new (α-d

  脱氢氨基酸 (Dhaa) 被认为是氨基酸和肽研究的有用工具或底物。尽管热力学上更稳定的 Z-Dhaa 的立体选择性合成已得到充分研究和确立，但 E-Dhaa 的立体选择性合成仍然是一项具有挑战性的合成任务。在本文中，描述了使用新的（α-二苯基膦酰基）甘氨酸立体选择性合成 E-Dhaa 酯。新方法的特征方面总结如下：（i）金属添加剂在促进 E 立体选择性方面起着重要作用。(ii) NaI 用于合成带有芳基取代基和氨基官能团的 E-Dhaas，
• Optically-active bis(alkynylphosphino) ethane-borane derivative and process for producing the same
  申请人：Imamoto Tsuneo

  公开号：US20080221362A1

  公开（公告）日：2008-09-11

  An optically-active bis(alkynylphosphino)ethane-borane derivative represented by formula (1): wherein R 1 and R 2 , which may be the same or different, each represent an alkyl group, a phenyl group, an alkylsilyl group or a hydrogen atom; R 3 represents a branched alkyl group, an alicyclic hydrocarbon group or an aromatic hydrocarbon group; and the asterisk * indicates an optically-active site. The derivative (1) is prepared by bromination of, e.g., an (S)-t-butylmethylphosphine-borane, reaction with an alkynyl lithium, deprotonation, followed by oxidative coupling. Deprotection of the derivative (1) by deboranation gives an optically-active bis(alkynylphosphino)ethane derivative useful as a ligand providing an asymmetric catalyst for catalytic asymmetric synthesis. The asymmetric catalyst having the ligand exhibits high selectivity and catalyst activity.

  公式（1）表示的具有光学活性的双(炔基膦)乙烷硼衍生物： 其中R1和R2，可以相同也可以不同，分别代表一个烷基基团、苯基、烷基硅基团或氢原子；R3代表一个支链烷基基团、脂环烃基团或芳香烃基团；星号*表示一个光学活性位点。 通过溴化，例如(S)-叔丁基甲基膦硼烷，与炔基锂反应，去质子化，然后进行氧化偶联制备衍生物（1）。通过去硼烷解保护衍生物（1），得到一种有用的作为提供不对称催化剂的光学活性双(炔基膦)乙烷衍生物，该催化剂具有高选择性和催化活性。
• Diphosphines, preparation and uses thereof
  申请人：Lemaire Marc

  公开号：US20070010695A1

  公开（公告）日：2007-01-11

  The invention concerns novel diphosphines of formula (I) useful in particular, in their optically active form, as ligands in metal complexes. The invention also concerns their uses an intermediates in the preparation of polymeric insoluble ligands. The invention further concerns the use of said insoluble ligands in the preparation of metal complexes for asymmetric. catalysis.

  该发明涉及公式（I）的新型二膦化合物，特别是它们的光学活性形式，在金属配合物中作为配体的有用性。该发明还涉及它们作为聚合物不溶性配体的中间体在制备中的用途。此外，该发明还涉及所述不溶性配体在制备用于不对称催化的金属配合物中的应用。
• Ferrocenyl Ligands For Homogeneous, Enantioselective Hydrogenation Catalysts
  申请人：Lotz Matthias

  公开号：US20080287698A1

  公开（公告）日：2008-11-20

  Compounds of the formula (I) or (I′), where R 1 is a hydrogen atom or C 1 -C 4 -alkyl and R′ 1 is C 1 -C 4 -alkyl; X 1 and X 2 are each, independently of one another, a secondary phosphine group; R 2 is hydrogen, R 01 R 02 R 03 Si—, C 1 -C 18 acyl substituted by halogen, hydroxy, C 1 -C 8 -alkoxy or R 04 R 05 N—, -or R 06 —X 01 —C(O)—; R 01 , R 02 and R 03 are each, independently of one another, C 1 -C 12 -alkyl, unsubstituted or C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy-substituted C 6 -C 10 -aryl or C 7 -C 12 -aralkyl; R 04 and R 05 are each, independently of one another, hydrogen, C 1 -C 12 -alkyl, C 3 -C 8 -cycloalkyl, C 6 -C 10 -aryl or C 7 -C 12 -aralkyl, or R 04 and R 05 together are trimethylene, tetramethylene, pentamethylene or 3-oxapcntylene; R 06 is C 1 -C 18 -alkyl, unsubstituted or C 1 -C 4 -alkyl- or C 1 -C 4 -alkoxy-substituted C 3 -C 8 -cycloalkyl, C 6 -C 10 -aryl or C 7 -C 12 -aralkyl; X 01 is —O— or —NH—; T is C 6 -C 20 -arylene; v is 0 or an integer from 1 to 4; and * denotes a mixture of racemic or enantiomerically pure diastereomers or pure racemic or enantiomerically diastereomers, are excellent chiral ligands for metal complexes as enantioselective catalysts for the hydrogenation of prochiral organic compounds.

  式(I)或(I′)的化合物，其中R1是氢原子或C1-C4-烷基，R′1是C1-C4-烷基；X1和X2分别是次磷酸基团；R2是氢，R01R02R03Si—，C1-C18酰基取代的卤素、羟基、C1-C8烷氧基或R04R05N—，或R06—X01—C(O)—；R01、R02和R03分别是C1-C12烷基、未取代或C1-C4烷基或C1-C4烷氧基取代的C6-C10芳基或C7-C12芳基烷基；R04和R05分别是氢、C1-C12烷基、C3-C8环烷基、C6-C10芳基或C7-C12芳基烷基，或者R04和R05一起是三亚甲基、四亚甲基、五亚甲基或3-氧代戊亚甲基；R06是C1-C18烷基，未取代或C1-C4烷基或C1-C4烷氧基取代的C3-C8环烷基、C6-C10芳基或C7-C12芳基烷基；X01是—O—或—NH—；T是C6-C20芳基；v是0或1到4的整数；*表示混合的外消旋或对映纯二对映体或纯外消旋或对映纯二对映体，对于金属络合物作为催化剂，对非手性有机化合物的氢化反应具有优异的手性配体。