3-Methyl-4-ethyl-3,4-dihydro-2H-benzoxazin | 70660-96-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 3-Methyl-4-ethyl-3,4-dihydro-2H-benzoxazin
• 英文别名: 4-ethyl-3-methyl-3,4-dihydro-2H-benzo[1,4]oxazine；4-Ethyl-3-methyl-2,3-dihydro-1,4-benzoxazine
• CAS: 70660-96-7
• 化学式: C₁₁H₁₅NO
• 分子量: 177.246
• InChiKey: PEXJJMJWWQTRQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(N-Benzyl-N-aethylamino)phenoxyaceton 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 生成 3-Methyl-4-ethyl-3,4-dihydro-2H-benzoxazin
  参考文献：
  名称：

  Der Einflu� von Stickstoffsubstituenten bei der Synthese von 3-Methyl-1,4-Benzoxazinen

  摘要：

  DOI：

  10.1007/bf00911913

文献信息

• Heteroaryl sulfonamides and CCR2
  申请人：ChemoCentryx, Inc.

  公开号：EP2354126A1

  公开（公告）日：2011-08-10

  A compound of the formula (I), or a salt thereof: where Ar is selected from the group consisting of substituted or unsubstituted C6-10 aryl and substituted or unsubstituted 5- to 10-membered heteroaryl; R1 is selected from the group consisting of hydrogen, unsubstituted C1 alkyl, substituted or unsubstituted C3-8 alkyl, substituted or unsubstituted C2-6alkenyl, substituted or unsubstituted C2-6 alkynyl, and substituted or unsubstituted 3- to 10-membered heterocyclyl; Y1 is selected from the group consisting of -CR2a-, -N-, and -N+(O)--; Y2 is selected from the group consisting of -CR2b-, -N-, and -N+(O)--; Y3 is selected from the group consisting of -CR2c-, -N-, and -N+(O)--; R2a, R2b, and R2c are each independently selected from the group consisting of hydrogen, halogen, -CN, -C(O)R3, -CO2R, -C(O)NR3R4, -OR3, -OC(O)R3, -OC(O)NR3R4, -SR3, -S(O)R3, -S(O)2R3, -S(O)2NR3R4, -NO2, -NR3R4, -NR3C(O)R4, -NR3C(O)OR4, - NR3S(O)2R4, -NR3C(O)NR4R5, substituted or unsubstituted C1-8 alkyl, substituted or unsubstituted C2-8 alkenyl, substituted or unsubstituted C2-8 alkynyl, substituted or unsubstituted 3- to 10-membered heterocyclyl, substituted or unsubstituted C6-10 aryl, and substituted or unsubstituted 5- to 10-membered heteroaryl; R3, R4, and R5 are each independently selected from the group consisting of hydrogen, substituted or unsubstituted C1-8 alkyl, substituted or unsubstituted C2-8 alkenyl, substituted or unsubstituted C2-8 alkynyl, substituted or unsubstituted C6-10 aryl, substituted or unsubstituted 5- to 10-membered heteroaryl, and substituted or unsubstituted 3- to 10-membered heterocyclyl; R3 and R4, R4 and R5 or R3 and R5 may, together with the atoms to which they are attached, form a substituted or unsubstituted 5-, 6-, or 7-membered ring; Y4 is selected from the group consisting of -N- and -N+(O)--; L is selected from the group consisting of a bond, -O-, -S-, -S(O)-, S(O)2-, -CR6R7-, - NR8-, -C(O)- and -NR8C(O)-; R6 and R7 are each independently selected from the group consisting of hydrogen, halogen, substituted or unsubstituted C1-8alkyl, substituted or unsubstituted 3- to 10-membered heterocyclyl, substituted or unsubstituted C2-6 alkenyl, substituted or unsubstituted C2-6alkynyl, -CN, -OR9, -NR10R11, -S(O)R9, and -S(O)2R9; R6 and R7 may, together with the carbon atom to which they are attached, form substituted or unsubstituted C3-8 cycloalkyl or substituted or unsubstituted 3- to 10-membered heterocyclic ring; R9 is selected from the group consisting of hydrogen, substituted or unsubstituted C1-8 alkyl, substituted or unsubstituted C2-8 alkenyl, substituted or unsubstituted C2-8 alkynyl, substituted or unsubstituted C6-10 aryl, substituted or unsubstituted 5- to 10-membered heteroaryl, and substituted or unsubstituted 3- to 10-membered heterocyclyl; R10 and R11 are each independently selected from the group consisting of substituted or unsubstituted C1-8 alkyl, substituted or unsubstituted 3- to 10-membered heterocyclyl, substituted or unsubstituted C6-10 aryl, substituted or unsubstituted 5- to 10-membered heteroaryl, substituted or unsubstituted C2-8 alkenyl, and substituted or unsubstituted C2-8alkynyl; R10 and R11 of -NR10R11 may, together with the nitrogen, form a substituted or unsubstituted C3-8 cycloalkyl or substituted or unsubstituted 3- to 10-membered heterocyclyl; R8 is selected from the group consisting of hydrogen, C(O)R12, S(O)2R12, CO2R12, substituted or unsubstituted C1-8alkyl, substituted or unsubstituted 3- to 10-membered heterocyclyl, substituted or unsubstituted C2-6 alkenyl, and substituted or unsubstituted C2-6 alkynyl; R12 is selected from the group consisting of substituted or unsubstituted C1-8alkyl, substituted or unsubstituted C2-6 alkenyl, substituted or unsubstituted C2-6 alkynyl, substituted or unsubstituted 3- to 1 0-membered heterocyclyl, substituted or unsubstituted C6-10 aryl, and substituted or unsubstituted 5- to 10-membered heteroaryl; Z1 is selected from the group consisting of substituted or unsubstituted C6-10 aryl, substituted or unsubstituted 5- to 10-membered heteroaryl, substituted or unsubstituted 3- to 10-membered heterocyclyl, and -NR13R14; R13 and R14 are each independently selected from the group consisting of hydrogen, substituted or unsubstituted C1-8 alkyl, substituted or unsubstituted C2-8 alkenyl, substituted or unsubstituted C2-8 alkynyl, substituted or unsubstituted 3- to 10-membered heterocyclyl, substituted or unsubstituted C6-10 aryl, substituted or unsubstituted 5- to 10-membered heteroaryl, substituted or unsubstituted (61-4 alkyl)-(C6-10 aryl), and substituted or unsubstituted (C1-4 alkyl)-(5- to 10-membered heteroaryl); R13 and R14 may, together with the nitrogen, form a substituted or unsubstituted 4-, 5-, 6-, or 7-membered heterocyclyl with the proviso that compounds of formula CC are excluded: where X14 is selected from the group consisting of -Cl, -NO2, -OCH3, -CH3, -NHC(O)CH3, and -CH2CH2-(phenyl); R65 is selected from the group consisting of hydrogen, substituted or unsubstituted C1-4 alkyl, and substituted or unsubstituted -SO2(phenyl); and R60 is selected from the group consisting of -NR61CH2CH2OR62, - NR61CH2CH2NR63R64, -NR61CH2CH2SR62, where R61 is selected from the group consisting of hydrogen and substituted or unsubstituted phenyl; R62 is selected from the group consisting of substituted or unsubstituted phenyl, and substituted or unsubstituted C1-4alkyl; and R63 and R64 are each independently selected from the group consisting of hydrogen, substituted or unsubstituted C1-8 alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted -SO2(phenyl), -C(O)CH3, -C(O)C(O)OH, and -C(O)2C(CH3)3.

  本发明涉及式(I)的化合物或其盐： 其中： - Ar选自取代或未取代的C6-10芳基和取代或未取代的5-10元杂芳基； - R1选自氢、未取代的C1烷基、取代或未取代的C3-8烷基、取代或未取代的C2-6烯基、取代或未取代的C2-6炔基，以及取代或未取代的3-10元杂环基； - Y1、Y2和Y3各自独立地选自-CR2a-、-N-和-N+ (O)--； - R2a、R2b和R2c各自独立地选自氢、卤素、-CN、-C(O)R3、-CO2R、-C(O)NR3R4、-OR3、-OC(O)R3、-OC(O)NR3R4、-SR3、-S(O)R3、-S(O)2R3、-S(O)2NR3R4、-NO2、-NR3R4、-NR3C(O)R4、-NR3C(O)OR4、-NR3S(O)2R4、-NR3C(O)NR4R5，取代或未取代的C1-8烷基、取代或未取代的C2-8烯基、取代或未取代的C2-8炔基、取代或未取代的3-10元杂环基、取代或未取代的C6-10芳基，以及取代或未取代的5-10元杂芳基； - R3、R4和R5各自独立地选自氢、取代或未取代的C1-8烷基、取代或未取代的C2-8烯基、取代或未取代的C2-8炔基、取代或未取代的C6-10芳基、取代或未取代的5-10元杂芳基，以及取代或未取代的3-10元杂环基； - R3和R4、R4和R5或R3和R5可能与所连接的原子一起形成取代或未取代的5-、6-或7元环； - Y4选自-N-和-N+ (O)--； - L选自键、-O-、-S-、-S(O)-、-S(O)2 -、-CR6R7 -= -NR8-、-C(O)-和-NR8C(O)-； - R6和R7各自独立地选自氢、卤素、取代或未取代的C1-8烷基、取代或未取代的3-10元杂环基、取代或未取代的C2-6烯基、取代或未取代的C2-6炔基、-CN、-OR9、-NR10R11、-S(O)R9和-S(O)2R9； - R6和R7可能与所连接的碳原子一起形成取代或未取代的C3-8环烷基或取代或未取代的3-10元杂环基； - R9选自氢、取代或未取代的C1-8烷基、取代或未取代的C2-8烯基、取代或未取代的C2-8炔基、取代或未取代的C6-10芳基、取代或未取代的5-10元杂芳基，以及取代或未取代的3-10元杂环基； - R10和R11各自独立地选自取代或未取代的C1-8烷基、取代或未取代的3-10元杂环基、取代或未取代的C6-10芳基、取代或未取代的5-10元杂芳基、取代或未取代的C2-8烯基，以及取代或未取代的C2-8炔基； - -NR10R11中的R10和R11可能与氮一起形成取代或未取代的C3-8环烷基或取代或未取代的3-10元杂环基； - R8选自氢、C(O)R12、S(O)2R12、CO2R12、取代或未取代的C1-8烷基、取代或未取代的3-10元杂环基、取代或未取代的C2-6烯基，以及取代或未取代的C2-6炔基； - R12选自取代或未取代的C1-8烷基、取代或未取代的C2-6烯基、取代或未取代的C2-6炔基、取代或未取代的3-10元杂环基、取代或未取代的C6-10芳基，以及取代或未取代的5-10元杂芳基； - Z1选自取代或未取代的C6-10芳基、取代或未取代的5-10元杂芳基、取代或未取代的3-10元杂环基，以及-NR13R14； - R13和R14各自独立地选自氢、取代或未取代的C1-8烷基、取代或未取代的C2-8烯基、取代或未取代的C2-8炔基、取代或未取代的3-10元杂环基、取代或未取代的C6-10芳基、取代或未取代的5-10元杂芳基、取代或未取代的(C1-4烷基)-(C6-10芳基)，以及取代或未取代的(C1-4烷基)-(5-10元杂芳基)； - R13和R14可能与氮一起形成取代或未取代的4-、5-、6-或7元杂环基； 其中化合物CC型被排除： 其中： - X14选自-Cl、-NO2、-OCH3、-CH3、-NHC(O)CH3和-CH2CH2-(苯基)； - R65选自氢、取代或未取代的C1-4烷基，以及取代或未取代的-SO2-苯基； - R60选自-NR61CH2CH2OR62、-NR61CH2CH2NR63R64，以及-NR61CH2CH2SR62； 其中： - R61选自氢和取代或未取代的苯基； - R62选自取代或未取代的苯基，以及取代或未取代的C1-4烷基； - R63和R64各自独立地选自氢、取代或未取代的C1-8烷基、取代或未取代的苯基、取代或未取代的-SO2-苯基、-C(O)CH3、-C(O)C(O)OH，以及-C(O)2C(CH3)3。
• BARTSCH H.; KROPP W.; PAILER M., MONATSH. CHEM., 1979, 110, NO 2, 257-265
  作者：BARTSCH H.、 KROPP W.、 PAILER M.

  DOI：——

  日期：——
• Kationische Azofarbstoffe, deren Herstellung und Verwendung beim Färben und Bedrucken von Textilmaterial
  申请人：CIBA-GEIGY AG

  公开号：EP0015872B1

  公开（公告）日：1983-03-30
• Naphtholactamverbindungen, Verfahren zu deren Herstellung sowie ihre Verwendung als Farbstoffe
  申请人：CIBA-GEIGY AG

  公开号：EP0017621B1

  公开（公告）日：1982-12-15
• US4332937A
  申请人：——

  公开号：US4332937A

  公开（公告）日：1982-06-01