α-methoxyimino-2-(2,5-dimethylphenoxymethyl)phenylacetonitrile | 156489-66-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: α-methoxyimino-2-(2,5-dimethylphenoxymethyl)phenylacetonitrile
• 英文别名: 2-(2,5-dimethylphenoxymethyl)-α-methoxyiminophenylacetonitrile；2-(2,5-dimethylphenoxymethyl)-α-methoxyiminobenzyl cyanide；(1E)-2-[(2,5-dimethylphenoxy)methyl]-N-methoxybenzenecarboximidoyl cyanide
• CAS: 156489-66-6
• 化学式: C₁₈H₁₈N₂O₂
• 分子量: 294.353
• InChiKey: VGPCMLITLVYION-JZJYNLBNSA-N

物化性质

• 沸点：
  430.6±47.0 °C(predicted)
• 密度：
  1.06±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  54.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  α-methoxyimino-2-(2,5-dimethylphenoxymethyl)phenylacetonitrile 在 盐酸 、 氢氧化钾 作用下， 生成 (Z)-2-[2-(2,5-dimethylphenoxymethyl)phenyl]-2-methoxyiminoacetic acid
  参考文献：
  名称：

  Process for producing alkoxyiminoacetamide compounds

  摘要：

  本文揭示了一种生产用作农业杀菌剂的烷氧基亚胺乙酰胺化合物的过程。还披露了上述过程的新型中间化合物及其生产。

  公开号：

  US05506358A1
• 作为产物：
  描述：

  2-[2-(2,5-dimethylphenoxymethyl)-phenyl]acetonitrile 在 sodium hydroxide 、 亚硝酸丁酯 、 硫酸二甲酯 作用下， 以 水 、 丙酮 、 甲苯 为溶剂， 生成 α-methoxyimino-2-(2,5-dimethylphenoxymethyl)phenylacetonitrile
  参考文献：
  名称：

  Process for producing (E)-alkoxyimino or hydroxyimino-acetamide

  摘要：

  本发明涉及一种生产(E)-烷氧基亚胺乙酰胺化合物的工艺，该化合物可用作农业杀菌剂，并涉及一种生产(E)-羟基亚胺乙酰胺化合物的工艺，该化合物可用作生产它们的中间体。本发明还涉及一种生产(E)-甲氧基亚胺乙酰胺化合物的工业过程，该化合物可用作农业杀菌剂。这个工艺在成本、安全性等方面具有优势。

  公开号：

  US05442063A1

文献信息

• Oxime derivative and bactericide containing the same as active ingredient
  申请人：Shionogi & Co., Ltd.

  公开号：US06048885A1

  公开（公告）日：2000-04-11

  A compound represented by general formula (I) or a salt thereof, a process for producing the same, an intermediate for the production thereof, and a bactericide (fungicide) containing the same as the active ingredient wherein R.sup.1 represent optionally substituted aryl, optionally substituted heterocycle, mono- or di-substituted methyleneamino, optionally substituted (substituted imino)methyl, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, substituted carbonyl or substituted sulfonyl; R.sup.2 represents alkyl, alkenyl, alkynyl or cycloalkyl; R.sup.3 represents optionally substituted heterocycle; R.sup.4 represents hydrogen, alkyl, alkoxy, halogen, nitro, cyano or haloalkyl; M represents oxygen, S(O)i (i being 0, 1 or 2), NR.sup.16 (R.sup.16 being hydrogen, alkyl or acyl) or a single bond; n represents 0 or 1, provided n represent 1 when R3 represents imidazol-1-yl or 1H-1, 2, 4-triazol-1-yl; and the symbol .about. represents the E form, Z form or a mixture thereof: ##STR1##

  由一般公式（I）表示的化合物或其盐，其制备方法，其生产的中间体以及含有其作为活性成分的杀菌剂（杀真菌剂），其中R.sup.1代表可选择地取代的芳基，可选择地取代的杂环烷基，单取代或双取代的亚甲基氨基，可选择地取代（取代亚氨基）甲基，可选择地取代的烷基，可选择地取代的烯基，可选择地取代的炔基，取代的羰基或取代的磺酰基；R.sup.2代表烷基，烯基，炔基或环烷基；R.sup.3代表可选择地取代的杂环烷基；R.sup.4代表氢，烷基，烷氧基，卤素，硝基，氰基或卤代烷基；M代表氧，S（O）i（i为0,1或2），NR.sup.16（R.sup.16为氢，烷基或酰基）或单键；n表示0或1，当R3表示咪唑-1-基或1H-1,2,4-三唑-1-基时，n为1；符号.约.代表E型，Z型或其混合形式：
• A process for producing (E)-alkoxyimino or hydroxyiminoacetamide compounds and intermediates therefor
  申请人：SHIONOGI SEIYAKU KABUSHIKI KAISHA

  公开号：EP0596692A2

  公开（公告）日：1994-05-11

  The present invention relates to a process for producing (E)-alkoxyiminoacetamide compounds useful as agricultural fungicides and a process for producing (E)-hydroxyiminoacetamide compounds useful as intermediates for producing them. The present invention also relates to an industrial process for producing (E)-methoxyiminoacetamide compounds useful as agricultural fungicides. This process is advantageous in terms of the cost, safety and the like.

  本发明涉及一种生产用作农用杀菌剂的(E)-烷氧基亚氨基乙酰胺化合物的工艺和一种生产用作生产(E)-羟基亚氨基乙酰胺化合物中间体的(E)-羟基亚氨基乙酰胺化合物的工艺。本发明还涉及一种生产用作农用杀菌剂的(E)-甲氧基亚氨基乙酰胺化合物的工业工艺。该工艺在成本、安全性等方面具有优势。
• PROCESS FOR PRODUCING CARBOXYLIC ACID DERIVATIVE
  申请人：SHIONOGI & CO., LTD.

  公开号：EP0658541A1

  公开（公告）日：1995-06-21

  A process for producing a carboxylic acid derivative represented by general formula [VIII], (wherein R¹, R², R³ and L are each as defined in the specification), which comprises reacting a benzyl halide with a cyano compound to give a phenylacetonitrile, reacting the nitrile with an alkyl nitrite in the presence of a base to give an α-hydroxyiminophenylacetonitrile, reacting the hydroxy nitrile with an alkylating agent to give an α-alkoxyiminophenylacetonitrile, hydrolyzing the alkoxy nitrile in the presence of a base, optionally after hydration and acid treatment, to give an α-alkoxyiminophenylacetic acid, and finally reacting the acid with a halogenating agent, or converting the acid into a corresponding metal salt and reacting the salt with an alkylating agent, or reacting the acid with a lower alcohol in the presence of an acidic catalyst. According to this process, the reactions can be advanced through the respective steps under mild conditions, and the target derivative [VIII] can be produced even without resort to high-pressure steam equipment, high-temperature heat medium equipment, refrigerator, and so forth. Further, this process is advantageous in that only a single solvent will suffice without the necessity for using various solvents according to the respective steps.

  一种生产通式[VIII]所代表的羧酸衍生物的工艺（其中R¹、R²、R³和L各自如说明书中所定义），该工艺包括将卤化苄基与氰基化合物反应，得到苯乙腈、在碱存在下，使腈与亚硝酸烷基酯反应，得到 α-羟基亚氨基苯乙腈，使羟基腈与烷化剂反应，得到 α-烷氧基亚氨基苯乙腈、在碱存在下，水解烷氧基腈（可选择在水合和酸处理后），得到 α-烷氧基亚氨基苯乙酸，最后使酸与卤化剂反应，或将酸转化为相应的金属盐并使盐与烷 化剂反应，或在酸性催化剂存在下使酸与低级醇反应。根据这种工艺，反应可以在温和的条件下通过相应的步骤进行，即使不使用高压蒸汽设备、高温热媒设备、冰箱等，也可以生产出目标衍生物[VIII]。此外，该工艺的优点还在于只需使用一种溶剂即可，而无需根据不同的步骤使用不同的溶剂。
• PROCESS FOR PRODUCING $g(a)-ALKOXYIMINOPHENYLACETONITRILE DERIVATIVE
  申请人：SHIONOGI & CO., LTD.

  公开号：EP0658543A1

  公开（公告）日：1995-06-21

  A process for producing an α-alkoxyiminophenylacetonitrile represented by general formula [III], (wherein R¹, R², R³ and Y are each as defined in the specification) by reacting an alkali metal salt of an α-hydroxyiminophenylacetonitrile, represented by general formula [I], (wherein R¹, R², Y and A are each as defined in the specification) with a dialkyl sulfate represented by the general formula [II]: (R³)₂SO₄, (wherein R³ is as defined in the specification) in the presence of a phase transfer catalyst in a solvent mixture composed of a hydrocarbon solvent and water. It is possible by using the above catalyst and solvent mixture to inhibit the formation of a nitrone derivative as a by-product to thereby produce a highly pure alkoxyimino compound in a high yield.

  一种生产通式[III]代表的α-烷氧基亚氨基苯乙腈(其中R¹、R²、R³和Y均如说明书中所定义)的工艺，其方法是将通式[I]代表的α-羟基亚氨基苯乙腈的碱金属盐(其中R¹、R²、Y和A均如说明书中所定义)与通式[II]代表的二烷基硫酸盐反应：(R³)₂SO₄，（其中 R³ 如说明书中所定义）在相转移催化剂存在下，在由烃溶剂和水组成的混合溶剂中进行。通过使用上述催化剂和混合溶剂，可以抑制作为副产物的腈酮衍生物的形成，从而高产率地生产出高纯度的烷氧基亚氨基化合物。
• Benzyl compounds and process for producing same
  申请人：SHIONOGI SEIYAKU KABUSHIKI KAISHA

  公开号：EP0741125A1

  公开（公告）日：1996-11-06

  A process for producing benzyl compounds of the formula: wherein A2 is alkyl, alkenyl, alkynyl, alkoxy, cycloalkyl, cycloalkenyl, optionally substituted phenyl or an optionally substituted heterocyclic group, and X is halogen, which comprises reacting a compound of the formula:         A2-OH   (II) with a compound of the formula (III): Also disclosed are certain novel benzyl compounds of the above formula and also derived from the above benzyl compounds. The compounds are useful intermediates in the preparation of (E)-alkoxyiminoacetamide compounds useful as agricultural fungicides.

  一种生产式苄基化合物的工艺： 其中A2是烷基、烯基、炔基、烷氧基、环烷基、环烯基、任选取代的苯基或任选取代的杂环基团，X是卤素，该工艺包括使式如下的化合物反应 A2-OH (II) 与式 (III) 的化合物反应： 还公开了某些上述式的新型苄基化合物以及由上述苄基化合物衍生的新型苄基化合物。 这些化合物是制备(E)-烷氧基亚氨基乙酰胺化合物的有用中间体，可用作农用杀菌剂。