methyl (E)-2-(hydroxyimino)-2-phenylacetate | 38114-34-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl (E)-2-(hydroxyimino)-2-phenylacetate
• 英文别名: 2-hydroxyimino-2-phenylacetic acid methyl ester；methyl (2E)-2-hydroxyimino-2-phenylacetate
• CAS: 38114-34-0
• 化学式: C₉H₉NO₃
• 分子量: 179.175
• InChiKey: LKVXRLSGZJUHDZ-CSKARUKUSA-N

物化性质

• 沸点：
  306.7±25.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  58.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (E)-2-(hydroxyimino)-2-phenylacetate 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.25h， 生成 N,N-dihexyl-2-phenylglycine methyl ester
  参考文献：
  名称：

  Double nucleophilic N-alkylation of α-oxime-esters with Grignard reagents

  摘要：

  Double nucleophilic N-alkylation of alpha-oxime-esters, affording N,N-dialkyl-alpha-amino acids is herein described. Grignard reagents accomplished double N-alkylations via umpolung and various N.N-dialkylated alpha-amino acids were successfully synthesized in 15 min. Both electron-withdrawing sulfonyl groups and electron-donating silyl and methyl groups on oximes were available. Alkylmagnesium species and (E)-configuration of alpha-oxime-ester were essential to this cascade reaction. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.08.091
• 作为产物：
  描述：

  苯甲酰甲酸甲酯 在 盐酸羟胺 、 三乙胺 作用下， 以 甲醇 为溶剂， 以13%的产率得到methyl (E)-2-(hydroxyimino)-2-phenylacetate
  参考文献：
  名称：

  Oxyiminoalkanoic acid derivatives with hypoglycemic and hypolipidemic activity

  摘要：

  本发明提供了一种新颖的氧亚氨基烷酸衍生物，该衍生物具有优异的降糖和降脂作用，用于治疗糖尿病、高脂血症、胰岛素不敏感、胰岛素抵抗和葡萄糖耐量受损。

  公开号：

  US06251926B1

文献信息

• Studies on Non-Thiazolidinedione Antidiabetic Agents. 1. Discovery of Novel Oxyiminoacetic Acid Derivatives.
  作者：Hiroshi Imoto、Eikoh Imamiya、Yu Momose、Yasuo Sugiyama、Hiroyuki Kimura、Takashi Sohda

  DOI：10.1248/cpb.50.1349

  日期：——

  A novel series of oxyiminoacetic acid derivatives were synthesized in an effort to develop a potent antidiabetic agent, which does not contain the 2,4-thiazolidinedione moiety. These compounds were evaluated for glucose and lipid lowering effects in genetically obese and diabetic KKAy mice. Several of the compounds showed strong antidiabetic activity, including functional potency at peroxisome proliferator-activated receptor (PPAR)-γ. (Z)-2-[4-[(5-Methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]benzyloxyimino]-2-(4-phenoxyphenyl)acetic acid (25) significantly reduced plasma glucose (33%, p<0.01) and plasma triglycelide levels (43%, p<0.01) even at a dosage of 0.001% in diet. Pharmacokinetic analyses of 25 are also reported.

  合成了一系列新型氧亚氨基乙酸衍生物，旨在开发不含有2,4-噻唑烷二酮部分的强效抗糖尿病药物。这些化合物在遗传性肥胖和糖尿病的KKAy小鼠中评估了其降低血糖和血脂的效果。其中几种化合物显示出强大的抗糖尿病活性，包括在过氧化物酶体增殖物激活受体（PPAR）-γ上的功能活性。(Z)-2-[4-[(5-甲基-2-苯基-1,3-噁唑-4-基)甲氧基]苄氧亚氨基]-2-(4-苯氧基苯基)乙酸（25）即使在饮食中含量仅为0.001%的剂量下，也能显著降低血浆葡萄糖水平（33%，p<0.01）和血浆甘油三酯水平（43%，p<0.01）。同时还报道了25的药代动力学分析。
• Oxime derivatives and the use thereof as photoinitiators
  申请人：Ciba Specialty Chemicals Holding Inc.

  公开号：EP1635220A2

  公开（公告）日：2006-03-15

  Radically photopolymerizable compositions comprising (a) at least one ethylenically unsaturated photopolymerizable compound; (b) as photoinitiator, at least one compound of the formula I, II, III and/or IV wherein m is 0 or 1; n is 0, 1, 2 or 3; x is 1 or 2; R1 is inter alia phenyl, naphthyl, anthracyl or phenanthryl, a heteroaryl radical, C2-C12alkenyl, C4-C8cycloalkenyl, or C6-C12bicycloalkenyl; R'1 is inter alia C2-C12alkylene, or phenylene; R2 has one of the meanings of R1 or inter alia is phenyl; y is 1 or 2; R3 if x is 1 inter alia is C1-C18alkylsulfonyl, or phenyl-C1-C3alkylsulfonyl, R3 if x is 2, is for example C2-C12alkylenedisulfonyl; R4 and R5 inter alia are hydrogen, halogen, or C1-C8alkyl; A is for example -S-, -O-, or -NR10-; R10 inter alia is hydrogen, or phenyl; and (c) at least one coinitiator; are especially suitable for the preparation of colour filter systems.

  具有根据公式I、II、III和/或IV的至少一种化合物作为光引发剂的(radically photopolymerizable compositions)，其中m为0或1；n为0、1、2或3；x为1或2；R1包括苯基、萘基、蒽基或菲基、杂环基、C2-C12烯基、C4-C8环烯基或C6-C12双环烯基；R'1包括C2-C12烷基、苯基或C2-C12烷基苯基；R2具有R1的含义之一或包括苯基；y为1或2；R3如果x为1，则包括C1-C18烷基磺酰基或苯基-C1-C3烷基磺酰基，如果x为2，则例如为C2-C12烷基二磺酰基；R4和R5包括氢、卤素或C1-C8烷基；A例如为-S-、-O-或-NR10-；R10包括氢或苯基等；并且至少包括一种协同引发剂，特别适用于制备彩色滤光片系统。
• Novel 6-chloro-2-(4,6-dimethoxypyrimidin-2-yl) oxybenzoic acid ester derivatives, processes for their production an a method for their application as herbicides
  申请人：LUCKY LTD.

  公开号：EP0608862A1

  公开（公告）日：1994-08-03

  The present invention relates to novel 6-chloro-2-(4,6-dimethoxypyrimidin-2-yl)oxybenzoic acid iminoester derivative of the general formula(I); processes for their preparation and a method for their application as herbicides:    Therein, Q represents a straight or branched alkyl, alkenyl or cycloalkyl group having from 1 to 10 carbon atoms, preferably from 1 to 8 carbon atoms, which may be substituted with a (C₁-C₄)alkoxy or (C₁-C₄)alkylthio group; a (C₁-C₄)alkyl or (C₂-C₄)alkenylthio group; a phenylthio group; a phenyl(C₁-C₄)alkyl or phenyl(C₂-C₄)alkenylthio group; or a radical of the following formula:    [wherein R¹ and R² are same or different each other and represent hydrogen or a halogen atom; or a group selected from the groups which comprised with a (C₁-C₄)alkyl, a (C₂-C₄)alkenyl, an acyl, an acyloxy, a (C₁-C₄)alkylthio, a nitro, a cyano, a phenyl and a phenoxy group, and which, if necessary, may be substituted with a halogen atom, a (C₁-C₄)alkyl, a (C₁-C₄)alkoxy or an acetal group; or R¹ and R² may constitute an acetal structure with carbon atoms to which R1 and R² are linked.; and, n is 0 or 1.]; or a 5-6 membered ring system containing one or more hetero atoms such as oxygen, sulfur or nitrogen atom in the ring system, which may have one or more proper substituents such as a halogen atom, a (C₁-C₄)alkyl, a hydroxy, a nitro or a cyano group on its certain positions.; and,    R represents a hydrogen or a halogen atom, a cyano group, or -Z -R³ [wherein, R³ represents a (C₁-C₄)alkyl, an alkoxy or alkenyloxyl group having from 1 to 8 carbon atoms, or a phenyl, a phenoxy or an amino group, or 5-6 membered hetero or aromatic ring system connecting to Z through out a (C₁-C₂)alkyl or alkoxy bridge, such as a phenyl, a furyl, a thienyl, pyrrolyl or pyranyl group, and which may have one or more proper substituents such as a halogen atom, a (C₁-C₄)alkyl, a hydroxy, a nitro or a cyano group on its certain positions, or R³ may be cyclized with Z and Q in some cases.; and, Z represents -O-, -S-, [wherein, R⁴ is a hydrogen atom, a (C₁-C₄)alkyl or a phenyl group, or constitutes a cyclic system containing an oxygen atom with R³]].

  本发明涉及一种新型的一般式(I)的6-氯-2-(4,6-二甲氧基嘧啶-2-基)氧基苯甲酸亚氨酯衍生物；它们的制备方法以及作为除草剂的应用方法：其中，Q代表具有1至10个碳原子的直链或支链烷基、烯基或环烷基，最好为具有1至8个碳原子的烷基，可以用(C₁-C₄)烷氧基或(C₁-C₄)烷硫基取代；(C₁-C₄)烷基或(C₂-C₄)烯基硫基；苯硫基；苯(C₁-C₄)烷基或苯(C₂-C₄)烯基硫基；或以下式的基团：[其中R¹和R²相同或不同，分别代表氢或卤素原子；或从由(C₁-C₄)烷基、(C₂-C₄)烯基、酰基、酰氧基、(C₁-C₄)烷硫基、硝基、氰基、苯基和苯氧基组成的群中选取的一种群，必要时可以用卤素原子、(C₁-C₄)烷基、(C₁-C₄)烷氧基或缩醛基取代；或R¹和R²可以构成与R1和R²连接的碳原子的缩醛结构；n为0或1]；或在环系统中含有一个或多个杂原子（如氧、硫或氮原子）的5-6元环系统，可以在其特定位置上具有一个或多个适当的取代基，如卤素原子、(C₁-C₄)烷基、羟基、硝基或氰基；R代表氢或卤素原子、氰基，或-Z-R³；其中，R³代表具有1至8个碳原子的(C₁-C₄)烷基、烷氧基或烯氧基，或苯、苯氧基或氨基，或通过(C₁-C₂)烷基或烷氧基桥连接到Z的5-6元杂原子或芳香环系统，如苯基、呋喃基、噻吩基、吡咯基或吡喃基，并且可以在其特定位置上具有一个或多个适当的取代基，如卤素原子、(C₁-C₄)烷基、羟基、硝基或氰基；或在某些情况下，R³可以与Z和Q环化；Z代表-O-、-S-，其中R⁴为氢原子、(C₁-C₄)烷基或苯基，或构成含氧原子的环系统与R³结合。
• Oxyiminoalkanoic acid derivatives
  申请人：——

  公开号：US20030186985A1

  公开（公告）日：2003-10-02

  To provide a novel oxyiminoalkanoic acid derivative which has excellent hypoglycemic and hypolipidemic actions and which is used for the prevention or treatment of diabetes mellitus, hyperlipemia, insulin insensitivity, insulin resistance and impaired glucose tolerance. A compound represented by the formula: 1 wherein R 1 is an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group; X is a bond, —CO—, —CH(OH)— or a group represented by —NR 6 — wherein R 6 is a hydrogen atom or an optionally substituted alkyl group; n is an integer of 1 to 3; Y is an oxygen atom, a sulfur atom, —SO—, —SO 2 — or a group represented by —NR 7 — wherein R 7 is a hydrogen atom or an optionally alkyl group; ring A is a benzene ring optionally having additional one to three substituents; p is an integer of 1 to 8; R 2 is a hydrogen atom, an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group; q is an integer of 0 to 6; m is 0 or 1; R 3 is a hydroxy group, OR 8 (R 8 is an optionally substituted hydrocarbon group.) or NR 9 R 10 (R 9 and R 10 are the same or different groups which are selected from a hydrogen atom, an optionally substituted hydrocarbon group, an optionally substituted heterocyclic group or an optionally substituted acyl group or R 9 and R 10 combine together to form a ring); R 4 and R 5 are the same or different groups which are selected from a hydrogen atom or an optionally substituted hydrocarbon group wherein R 4 may form a ring with R 2 ; provided that when R 1 is a ethoxymethyl, a C 1-3 alkyl, phenyl or p-methoxyphenyl and q=m=0, R 3 is NR 9 R 10 ; and provided that O-[2-chloro-4-(2-quinolylmethoxy)phenylmethyl]oxime and a methylpyruvate of [2-chloro-4-(2-quinolylmethoxy)phenylmethyl]-2-iminoxypropionic acid are excluded; or a salt thereof.

  提供一种新型的氧亚胺基脂肪酸衍生物，具有优异的降血糖和降血脂作用，并用于预防或治疗糖尿病、高脂血症、胰岛素不敏感、胰岛素抵抗和糖耐量受损。该化合物的结构式为1，其中R1是可选取的取代的碳氢化合物基团或可选取的取代的杂环基团；X是键，-CO-，-CH（OH）-或由-NR6-表示的基团（其中R6是氢原子或可选取的取代的烷基基团）；n是1到3的整数；Y是氧原子、硫原子、-SO-，-SO2-或由-NR7-表示的基团（其中R7是氢原子或可选取的烷基基团）；环A是苯环，可选取具有1到3个附加取代基团；p是1到8的整数；R2是氢原子、可选取的取代的碳氢化合物基团或可选取的取代的杂环基团；q是0到6的整数；m是0或1；R3是羟基、OR8（其中R8是可选取的取代的碳氢化合物基团）或NR9R10（其中R9和R10是相同或不同的基团，选自氢原子、可选取的取代的碳氢化合物基团、可选取的取代的杂环基团或可选取的取代的酰基，或R9和R10结合形成环）；R4和R5是相同或不同的基团，选自氢原子或可选取的取代的碳氢化合物基团，其中R4可以与R2形成环；但当R1为乙氧甲基、C1-3烷基、苯基或对甲氧基苯基且q=m=0时，R3为NR9R10；且不包括O-[2-氯-4-(2-喹啉基甲氧基)苯甲基]肟和[2-氯-4-(2-喹啉基甲氧基)苯甲基]-2-亚氨基丙酸甲酯；或其盐。
• [EN] OXYIMINOALKANOIC ACID DERIVATIVES WITH HYPOGLYCEMIC AND HYPOLIPIDEMIC ACTIVITY<br/>[FR] DERIVES D'ACIDE OXYMINOALCANOIQUE AYANT UN EFFET HYPOGLYCEMIQUE ET HYPOLIPIDEMIQUE
  申请人：TAKEDA CHEMICAL INDUSTRIES, LTD.

  公开号：WO1999058510A1

  公开（公告）日：1999-11-18

  (EN) To provide a novel oxyiminoalkanoic acid derivative which has excellent hypoglycemic and hypolipidemic actions and which is used for the prevention or treatment of diabetes mellitus, hyperlipemia, insulin insensitivity, insulin resistance and impaired glucose tolerance. A compound represented by formula (a) wherein R1 is an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group; X is a bond, -CO-, -CH(OH)- or a group represented by -NR6- wherein R6 is a hydrogen atom or an optionally substituted alkyl group; n is an integer of 1 to 3; Y is an oxygen atom, a sulfur atom, -SO-, -SO2- or a group represented by -NR7- wherein R7 is a hydrogen atom or an optionally alkyl group; ring A is a benzene ring optionally having additional one to three substituents; p is an integer of 1 to 8; R2 is a hydrogen atom, an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group; q is an integer of 0 to 6; m is 0 or 1; R3 is a hydroxy group, OR8 (R8 is an optionally substituted hydrocarbon group) or NR9R10 (R9 and R10 are the same or different groups which are selected from a hydrogen atom, an optionally substituted hydrocarbon group, an optionally substituted heterocyclic group or an optionally substituted acyl group or R9 and R10 combine together to form a ring); R4 and R5 are the same or different groups which are selected from a hydrogen atom or an optionally substituted hydrocarbon group wherein R4 may form a ring with R2; provided that when R1 is a ethoxymethyl, a C1-3 alkyl, phenyl or p-methoxyphenyl and q=m=0, R3 is NR9R10; and provided that O-[2-chloro-4-(2-quinolylmethoxy)phenylmethyl]oxime and a methyl pyruvate of [2-chloro-4-(2-quinolylmethoxy)phenylmethyl]-2-iminoxypropionic acid are excluded; or a salt thereof.(FR) On décrit un composé de la formule (a), ou un sel dudit composé, qui donne un nouveau dérivé d'acide oxyminoalcanoïque ayant un excellent effet hypoglycémique et hypolipidémique, et s'utilise pour la prévention ou le traitement du diabète sucré, de l'hyperlipémie, de l'insensibilité à l'insuline, de la résistance à l'insuline et de l'intolérance au glucose. Dans ladite formule, R1 est un groupe hydrocarbure éventuellement substitué ou un groupe hétérocyclique éventuellement substitué; X est une liaison -CO-, -CH(OH)- ou un groupe représenté par -NR6- (R6 étant un atome d'hydrogène ou un groupe alkyle éventuellement substitué); n est un entier compris entre 1 et 3; Y est un atome d'oxygène, un atome soufre, -SO-, -SO2- ou un groupe représenté par -NR7- (R7 étant un atome d'hydrogène ou un groupe alkyle éventuellement substitué; le noyau A est un noyau benzénique ayant éventuellement un à trois substituants complémentaires; p est un entier compris entre 1 et 8; R2 est un atome d'hydrogène, un groupe hydrocarbure éventuellement substitué ou un groupe hétérocyclique éventuellement substitué; q est un entier compris entre 0 et 6; m est 0 ou 1; R3 est un groupe hydroxy, OR8 (R8 étant un groupe hydrocarbure éventuellement substitué) ou NR9R10 (R9 et R10 étant des groupes identiques ou différents sélectionnés dans le groupe constitué par un atome d'hydrogène, un groupe hydrocarbure éventuellement substitué, un groupe hétérocyclique éventuellement substitué ou groupe acyle éventuellement substitué, ou R9 et R10 forment ensemble un noyau); R4 et R5 sont des groupes identiques ou différents sélectionnés dans le groupe constitué par un atome d'hydrogène ou un groupe hydrocarbure éventuellement substitué (R4 pouvant former un noyau avec R2); à condition que, d'une part, si R1 est éthoxyméthyle, un alkyle C1-3, phényle ou p-méthoxyphényle et que q=m=0, R3 soit NR9R10; et, d'autre part que O-[2-chloro-4-(2-quinolylméthoxy)phénylméthyl]oxime et un pyruvate de méthyle d'acide [2-chloro-4-(2-quinolylméthoxy)phénylméthyl]-2-iminoxypropionique soient exclus.

  提供一种新型的氧亚胺基脂肪酸衍生物，具有优异的降血糖和降血脂作用，可用于预防或治疗糖尿病、高脂血症、胰岛素不敏感、胰岛素抵抗和糖耐量受损。该化合物由公式(a)表示，其中R1是可选取代的碳氢化合物基团或可选取代的杂环基团；X是键合，-CO-，-CH（OH）-或由-NR6-表示的基团，其中R6是氢原子或可选取代的烷基基团；n是1至3的整数；Y是氧原子、硫原子、-SO-，-SO2-或由-NR7-表示的基团，其中R7是氢原子或可选取代的烷基基团；环A是苯环，可选具有1至3个补充取代基团；p是1至8的整数；R2是氢原子、可选取代的碳氢化合物基团或可选取代的杂环基团；q是0至6的整数；m是0或1；R3是羟基、OR8（其中R8是可选取代的碳氢化合物基团）或NR9R10（其中R9和R10是从氢原子、可选取代的碳氢化合物基团、可选取代的杂环基团或可选取代的酰基基团中选择的相同或不同基团，或R9和R10结合形成一个环）；R4和R5是从氢原子或可选取代的碳氢化合物基团中选择的相同或不同基团，其中R4可以与R2形成环；前提是当R1是乙氧甲基、C1-3烷基、苯基或对甲氧基苯基且q=m=0时，R3为NR9R10；并且排除O-[2-氯-4-(2-喹啉基甲氧基)苯甲基]肟和[2-氯-4-(2-喹啉基甲氧基)苯甲基]-2-亚氨基丙酸的甲酯；或其盐。