α-cyano-β-ethoxy-N-ethoxycarbonylacrylamide | 869116-51-8

• 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: α-cyano-β-ethoxy-N-ethoxycarbonylacrylamide
• 英文别名: (E)-ethyl (2-cyano-3-ethoxyacryloyl)carbamate；E-ethyl (2-cyano-3-ethoxyacryloyl)carbamate；(3t-ethoxy-2-cyano-acryloyl)-carbamic acid ethyl ester；(3t-Aethoxy-2-cyan-acryloyl)-carbamidsaeure-aethylester；N-(2-cyano-3-ethoxyacryloyl)urethane；Ethyl (2-cyano-3-ethoxyacryloyl)carbamate；ethyl N-[(E)-2-cyano-3-ethoxyprop-2-enoyl]carbamate
• CAS: 869116-51-8
• 化学式: C₉H₁₂N₂O₄
• 分子量: 212.205
• InChiKey: JNZGHWBZWCEXEJ-VOTSOKGWSA-N

物化性质

• 密度：
  1.181±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  88.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  α-cyano-β-ethoxy-N-ethoxycarbonylacrylamide 在 三乙胺 作用下， 以 氘代氯仿 、 氘代乙腈 为溶剂， 反应 28.0h， 生成 2,4-二氧代-1-苯基-1,2,3,4-四氢-5-嘧啶甲腈
  参考文献：
  名称：

  A multi-component reaction to 5-cyanouracils: Synthesis and mechanistic study

  摘要：

  Acetonitrile as a solvent, excess of primary amines as general bases, and a reflux condition make the multi-component reactions of (2-cyanoacetyl) carbamate 1, ethyl orthoformate, and primary amines form 5-cyanouracils 4a-c feasibly. Mechanistic studies of the multi-component reaction were carried out by proton NMR spectrometer. Acetonitrile as a solvent makes the reaction of 1 with ethyl orthoformate produce E-ethyl (2-cyano-3-ethoxyacryloyl) carbamate E-2 without a catalyst of acetic anhydride. The reactions of E-2 with primary amines produce the corresponding Z-3a-c as the only stable isomers eventually in CDCl3 or CD3CN. General-base-catalyzed intramolecular cyclizations of Z-3a-c at a reflux condition in CD3CN generated the corresponding 5-cyanouracils 4a-c. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.12.059
• 作为产物：
  描述：

  (Z)-2-cyano-3-ethoxyacryl ethyl carbamate 反应 48.0h， 生成 α-cyano-β-ethoxy-N-ethoxycarbonylacrylamide
  参考文献：
  名称：

  为什么（2-氰基乙酰基）氨基甲酸乙酯与原甲酸乙酯的反应具有高度的立体选择性？

  摘要：

  （2-氰基乙酰基）氨基甲酸乙酯（1）与原甲酸乙酯在乙酸酐存在下的反应是高度立体选择性的，并且仅分离出E-乙基（2-氰基-3-乙氧基丙烯酰基）氨基甲酸酯（E - 2）。反应是热力学控制的，产物的分布取决于E - 2和Z - 2之间的相对稳定性。1.47 kcal mol -1的共振稳定度和2.28 kcal mol -1的空间位阻（有利于E - 2）都有助于相对稳定性（3.75 kcal mol -1）之间ž - 2和ë - 2，这是从四个键反应来计算，这就是为什么化合物的反应的原因1与原甲酸乙酯是高度立体选择性。评价了一些取代基的吸电子能力。π接受能力的顺序为C（O）NHC（O）OEt> C（O）NH 2  > CN和σ接受能力的顺序为CN> C（O）NHC（O）OEt> C（O ）NH 2。版权所有©2005 John Wiley＆Sons，Ltd.

  DOI：

  10.1002/poc.979

文献信息

• Pyrimidine derivatives useful as inhibitors of PKC-theta
  申请人：Barbosa J.M. Antonio

  公开号：US20060025433A1

  公开（公告）日：2006-02-02

  Disclosed are novel compounds of formula (I): wherein X, Y, R 1 , R 2 and R 3 are as defined herein, which are useful as inhibitors of PKC-theta and are thus useful for treating a variety of diseases and disorders that are mediated or sustained through the activity of PKC-theta, including immunological disorders and type II diabetes. This invention also relates to pharmaceutical compositions comprising these compounds, methods of using these compounds in the treatment of various diseases and disorders, processes for preparing these compounds and intermediates useful in these processes.

  披露了公式(I)的新颖化合物：其中X、Y、R1、R2和R3如本文所述定义，它们作为PKC-theta的抑制剂是有用的，因此可用于治疗通过PKC-theta活性介导或维持的多种疾病和失调，包括免疫失调和II型糖尿病。本发明还涉及包含这些化合物的药物组合物、使用这些化合物治疗各种疾病和失调的方法、制备这些化合物的方法以及在这些过程中有用的中间体。
• Synthesis of optically active-α-(imidazol-1-yl, purin-9-yl or uracil-1-yl) propanoic and succinic acid derivatives
  作者：Paul R. Birkett、Hazel King、Christopher B. Chapleo、David F. Ewing、Grahame Mackenzie

  DOI：10.1016/s0040-4020(01)80256-8

  日期：1993.1

  An efficient route is reported to chiral propanoic and succinic acid derivatives substituted in the α-position with adenine, hypoxanthine and uracil groups. These nucleic acid base derivatives are obtained in optically pure form by a procedure which starts from an amino acid as a convenient chiral synthon.

  据报道，一种有效的途径是在α位上被腺嘌呤，次黄嘌呤和尿嘧啶基团取代的手性丙酸和琥珀酸衍生物。这些核酸碱基衍生物是通过从氨基酸开始的方便手性合成子的方法以光学纯的形式获得的。
• Azabicyclo[3.1.0]hex-3-yl}alkyl)pyrimidinedione
  申请人：Bertani Barbara

  公开号：US20070249642A1

  公开（公告）日：2007-10-25

  The present invention relates to novel compounds of formula (I)′ or a salt thereof: wherein G is selected from a group consisting of: phenyl, a 5- or 6-membered monocyclic heteroaryl group, or a 8- to 11-membered heteroaryl bicyclic group; A is a group P1 or a group P2 wherein P1 is and the other groups are define in herein.

  本发明涉及式（I）'的新化合物或其盐：其中G从以下群组中选择：苯基，5-或6-成员单环杂芳基团，或8-至11-成员杂芳双环基团；A是P1基团或P2基团，其中P1是，而其他基团在此处定义。
• PYRIMIDINE DERIVATIVES USEFUL AS INHIBITORS OF PKC-THETA
  申请人：BARBOSA Antonio J.M.

  公开号：US20080287410A1

  公开（公告）日：2008-11-20

  Disclosed are novel compounds of formula (I): wherein X, Y, R 1 , R 2 and R 3 are as defined herein, which are useful as inhibitors of PKC-theta and are thus useful for treating a variety of diseases and disorders that are mediated or sustained through the activity of PKC-theta, including immunological disorders and type II diabetes. This invention also relates to pharmaceutical compositions comprising these compounds, methods of using these compounds in the treatment of various diseases and disorders, processes for preparing these compounds and intermediates useful in these processes.

  本发明涉及一种新型化合物，其化学式为（I）：其中X，Y，R1，R2和R3的定义如本文所述，该化合物可用作PKC-theta的抑制剂，因此可用于治疗多种通过PKC-theta的活性介导或维持的疾病和疾病，包括免疫性疾病和2型糖尿病。本发明还涉及包含这些化合物的制药组合物，使用这些化合物治疗各种疾病和疾病的方法，制备这些化合物的过程以及在这些过程中有用的中间体。
• URACIL DERIVATIVE AND USE THEREOF FOR MEDICAL PURPOSES
  申请人：Shiro Tomoya

  公开号：US20140179670A1

  公开（公告）日：2014-06-26

  The present invention provides: an uracil derivative represented by general formula (I) or a physiologically acceptable salt thereof (in the formula, R 1 represents a hydrogen atom, a C 1-10 alkyl group, a C 2-6 alkene group or a 3- to 6-membered saturated or 4- to 6-membered unsaturated aliphatic ring group which may contain 1 to 2 hetero atoms independently selected from the group consisting of N, O and S; R 2 represents a hydrogen atom, a halogen atom, a cyano group, —NR c R d , —N═CHN(CH 3 ) 2 , or an C 1-3 alkyl group; Ar 1 and Ar 2 independently represent a 5- to 6-membered aromatic ring group which may contain 1 to 3 hetero atoms independently selected from the group consisting of N, O and S; and L represents a 6-membered aromatic ring group which may contain 1 to 4 nitrogen atoms, a pyrazole group, a triazole group, or an imidazole group); and a therapeutic agent or prophylactic agent for various inflammatory diseases associated with elastase, comprises the compound or the like as an active ingredient.

  本发明提供：一种尿嘧啶衍生物，其由通式（I）表示，或其生理上可接受的盐（在该式中，R1代表氢原子，C1-10烷基，C2-6烯基或3-至6-成员饱和或4-至6-成员不饱和的脂肪环基，该环基可以独立地选择来自N，O和S的1到2个杂原子；R2代表氢原子，卤素原子，氰基，—NRcRd，—N═CHN(CH3)2或C1-3烷基；Ar1和Ar2独立地表示5-至6-成员芳香环基，该环基可以独立地选择来自N，O和S的1到3个杂原子；L表示6-成员芳香环基，该环基可以包含1到4个氮原子，吡唑基，三唑基或咪唑基）；以及用作与弹性酶相关的各种炎症性疾病的治疗剂或预防剂，包括该化合物或类似物作为活性成分。