3-(Furan-2-ylmethyl-methyl-carbamoyl)-2-hydroxy-acrylic acid | 1232682-57-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-(Furan-2-ylmethyl-methyl-carbamoyl)-2-hydroxy-acrylic acid
• 英文别名: (Z)-4-[furan-2-ylmethyl(methyl)amino]-2-hydroxy-4-oxobut-2-enoic acid
• CAS: 1232682-57-3
• 化学式: C₁₀H₁₁NO₅
• 分子量: 225.201
• InChiKey: MOLJZCMIKNVHFV-YVMONPNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  91
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (2Z)-2-(2,2-dimethyl-5-oxo-1,3-dioxolan-4-ylidene)-N-(furan-2-ylmethyl)-N-methylacetamide 在 sodium hydroxide 作用下， 以 水 为溶剂， 以95%的产率得到3-(Furan-2-ylmethyl-methyl-carbamoyl)-2-hydroxy-acrylic acid
  参考文献：
  名称：

  (Z)-2,2-Dimethyl-5-carboxymethylene-1,3-dioxolan-4-one: a new synthon for the synthesis of α,γ-diketoacid derivatives

  摘要：

  The synthesis and reactivity of (Z)-2,2-dimethyl-5-carboxymethylene-1,3-dioxolan-4-one, a new and versatile synthon useful for the synthesis of selectively protected alpha,gamma-diketoacid derivatives, are described. This new, protected form of hydroxyl fumaric acid along with its acid chloride was used to prepare ester, amide, and aryl derivatives. The dioxolane moiety was found to be a convenient functionality that facilitated ready unmasking by straightforward hydrolysis to reveal alpha,gamma-diketoacid derivatives or derivatization to yield ester, amide, and 2,3-pyrrolidinedione derivatives. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.04.032

文献信息

• HIV integrase inhibitors
  申请人：——

  公开号：US20030181490A1

  公开（公告）日：2003-09-25

  The present invention relates to the inhibition of HIV integrase, and to the treatment of AIDS or ARC by administering compounds of the formula 1 wherein R 1 is C 1 -C 4 alkyl, carbocyclic radical, heterocyclic radical, aryl-C 1 -C 2 alkylene, aryloxy-C 1 -C 2 alkylene, alkoxy-CC(O)—, wherein R 1 is optionally substituted from 1-3 times with halo, C 1 -C 2 alkyl or C 1 -C 2 alkoxy, or R 1 is H; R 2 is H or C 1 -C 4 alkyl; R 3 is H, C 1 -C 4 alkyl or phenyl-C 0 -C 2 alkylene which is optionally substituted with 1-3 R 5 ; R 4a is carbocylic radical, heterocyclic radical, aryloxy, aryl-C 1 -C 4 alkylene, aryl-cyclopropylene, aryl-NHC(O)—, wherein R 4a is optionally substituted with 1-3 R 5 ; and wherein each R 5 is independently selected from H, halo, C 1 -C 4 alkyl, C 1 -C 4 alkenyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, R 6 -phenyl, R 6 -phenoxy, R 6 -benzyl, R 6 -benzyloxy, NH 2 C (O)—, alkyl-NHC(O)—, wherein R 6 is H, halo; Z is a bond or a substituted or unsubstituted C 1 -C 4 alkylene group; and B 2 is 2

  本发明涉及抑制HIV整合酶的化合物，并通过给予式1中的化合物治疗艾滋病或ARC，其中R1为C1-C4烷基，碳环基，杂环基，芳基-C1-C2烷基，芳氧基-C1-C2烷基，烷氧基-CC（O）-，其中R1可以用卤素，C1-C2烷基或C1-C2烷氧基从1-3次取代，或R1为H；R2为H或C1-C4烷基；R3为H，C1-C4烷基或苯基-C0-C2烷基，该苯基-C0-C2烷基可以选择性地用1-3个R5取代；R4a为碳环基，杂环基，芳氧基，芳基-C1-C4烷基，芳基环丙基，芳基-NHC（O）-，其中R4a可以选择性地用1-3个R5取代；每个R5都是独立选择的H，卤素，C1-C4烷基，C1-C4烯基，C1-C4卤代烷基，C1-C4烷氧基，R6-苯基，R6-苯氧基，R6-苄基，R6-苄氧基，NH2C（O）-，烷基-NHC（O）-，其中R6为H，卤素；Z为键或取代或未取代的C1-C4烷基；B2为2。
• HIV INTEGRASE INHIBITORS
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：EP1322599A2

  公开（公告）日：2003-07-02
• US6803378B2
  申请人：——

  公开号：US6803378B2

  公开（公告）日：2004-10-12
• [EN] HIV INTEGRASE INHIBITORS<br/>[FR] INHIBITEURS D'INTEGRASE DU VIH
  申请人：——

  公开号：WO2001096283A9

  公开（公告）日：2002-10-17

  [EN] The present invention relates to the inhibition of HIV integrase, and to the treatment of AIDS or ARC by administering compounds of the formula (Ia) wherein R<1> is C1-C4 alkyl, carbocyclic radical, heterocyclic radical, aryl-C1-C2 alkylene, aryloxy-C1-C2 alkylene, alkoxy-CC(O)-, wherein R<1> is optionally substituted from 1-3 times with halo, C1-C2 alkyl or C1-C2 alkoxy, or R<1> is H; R<2> is H or C1-C4 alkyl; R<3> is H, C1-C4 alkyl or phenyl-C0-C2 alkylene which is optionally substituted with 1-3 R<5>; R<4a> is carbocylic radical, heterocyclic radical, aryloxy, aryl-C1-C4 alkylene, aryl-cyclopropylene, aryl-NHC(O)-, wherein R<4a> is optionally substituted with 1-3 R<5>; and wherein each R<5> is independently selected from H, halo, C1-C4 alkyl, C1-C4 alkenyl, C1-C4 haloalkyl, C1-C4 alkoxy, R<6>-phenyl, R<6>-phenoxy, R<6>-benzyl, R<6>-benzyloxy, NH2C(O)-, alkyl-NHC(O)-, wherein R<6> is H, halo; Z is a bond or a substituted or unsubstituted C1-C4 alkylene group; and B<2> is formula (a), (b), or (c).
  [FR] La présente invention concerne l'inhibition de l'intégrase du VIH ainsi que le traitement du SIDA ou du para-SIDA par l'administration de composés de la formule (Ia) dans laquelle R<1> représente alkyle C1-C4, un radical carbocyclique, un radical hétérocyclique, aryle-alkylène C1-C2, aryloxy-alkylène C1-C2, alcoxy-CC(O)-, où R<1> est facultativement substitué de une à trois fois par halo, alkyle C1-C2 ou alcoxy C1-C2, ou R<1> représente H; R<2> représente H ou alkyle C1-C4; R<3> représente H, alkyle C1-C4 ou phényle-alkylène C0-C2 lequel est facultativement substitué par 1-3 R<5>; R<4>a représente un radical carbocyclique, un radical hétérocyclique, aryloxy, aryle-alkylène C1-C4, aryle-cyclopropylène, aryle-NHC(O)-, où R<4>a est facultativement substitué par 1-3 R<5>; et dans laquelle chaque R<5> est sélectionné indépendamment entre H, halo, alkyle C1-C4, alcényle C1-C4, haloalkyle C1-C4, alcoxy C1-C4, R<6>-phényle, R<6>-phénoxy, R<6>-benzyle, R<6>-benzyloxy, NH2C(O)-, alkyle-NHC(O)-, où R<6> représente H, halo; Z représente une liaison ou un groupe alkylène C1-C4 substitué ou non substitué; et B<2> représente (a), (b) ou (c).
• (Z)-2,2-Dimethyl-5-carboxymethylene-1,3-dioxolan-4-one: a new synthon for the synthesis of α,γ-diketoacid derivatives
  作者：Jacques Banville、Gilles Bouthillier、Serge Plamondon、Roger Remillard、Nicholas A. Meanwell、Alain Martel、Michael A. Walker

  DOI：10.1016/j.tetlet.2010.04.032

  日期：2010.6

  The synthesis and reactivity of (Z)-2,2-dimethyl-5-carboxymethylene-1,3-dioxolan-4-one, a new and versatile synthon useful for the synthesis of selectively protected alpha,gamma-diketoacid derivatives, are described. This new, protected form of hydroxyl fumaric acid along with its acid chloride was used to prepare ester, amide, and aryl derivatives. The dioxolane moiety was found to be a convenient functionality that facilitated ready unmasking by straightforward hydrolysis to reveal alpha,gamma-diketoacid derivatives or derivatization to yield ester, amide, and 2,3-pyrrolidinedione derivatives. (C) 2010 Elsevier Ltd. All rights reserved.