6-(5'-Methyl-2'-hydroxyphenyl)-2-formyl-pyridine | 1042159-36-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 6-(5'-Methyl-2'-hydroxyphenyl)-2-formyl-pyridine
• 英文别名: 6-(2-hydroxy-5-methylphenyl)pyridine-2-carbaldehyde
• CAS: 1042159-36-3
• 化学式: C₁₃H₁₁NO₂
• 分子量: 213.236
• InChiKey: QNWKKYMMQZAFDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(5'-Methyl-2'-hydroxyphenyl)-2-formyl-pyridine 、 2,6-二异丙基苯胺 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 以72%的产率得到(E)-2-(6-(((2,6-diisopropylphenyl)imino)methyl)pyridin-2-yl)-4-methylphenol
  参考文献：
  名称：

  Use of Suzuki cross-coupling as a route to 2-phenoxy-6-iminopyridines and chiral 2-phenoxy-6-(methanamino)pyridines

  摘要：

  The anisyl boronic acids, 2-OMe-3-R-2-5-R-1-C6H2B(OH)(2) (R-1=R-2=H (a); R-1=H, R-2=Ph (b); R-1=Me, R-2=H (c); R-1=Cl, R-2=H (d); R-1=t-Bu, R-2=H (e)), have been employed in Suzuki cross-coupling reactions with either 2-bromo-6-formylpyridine (1) or 2-bromo-6-acetylpyridine (11) generating, following a facile deprotection step, the 2-phenoxy-6-carbonylpyridines, 2-(2'-OH-3'-R-2-5'-R-1-C6H2)-6-(CH=O)C5H3N (R-1=R-2=H (1a); R-1=Me, R-2=H (1c); R-1=Cl, R-2=H (1d); R-1=t-Bu, R-2=H (1e)) and 2-(2'-OH-3'-R-2-5'-R-1-C6H2)-6-(CMe=O)C5H3N (R-1=R-2=H (2a); R-1=H, R-2=Ph (2b)). Condensation reactions of 1 and 2 with 2,6-diisopropylaniline proceed smoothly to give the 2-phenoxy-6-iminopyridines, 2-(2'-OH-3'-R-2-5'-R-1-C6H2)-6-{CH=N(2,6-i-Pr2C6H3)}C5H3N (R-1=R-2=H (3a); R-1=Me, R-2=H (3c); R-1=Cl, R-2=H (3d); R-1=t-Bu, R-2=H (3e)) and 2-(2'-OH-3'-R-2-5'-R-2-C6H2)-6-{CMe=N(2,6-i-Pr2C6H3)}C5H3N (R-1=H, R-2=Ph (4a), R-1=H, R-2=Ph (4b)). Reduction of the imino unit (and concomitant C-C bond formation) in 3 can be achieved by treatment with trimethylaluminium or methyllithium which, following hydrolysis, furnishes the racemic chiral 2-phenoxy-6-(methanamino)pyridines, 2-(2'-OH-3'-R-2-5'-R-1-C6H2)-6-{CHMe-NH(2,6-i-Pr2C6H3)}C5H3N {R-1=R-2=H (5a); R-1=Me, R-2=H (5c); R-1=Cl, R-2=H (5d); R-1=t-Bu, R-2=H (5e)). This work represents a straightforward and rapid synthetic route to libraries of sterically and electronically variable phenoxy-substituted imino- and methanamino-pyridines, which are expected to act as useful ligands or proligands for late and early transition metal-mediated alkene polymerisation catalysis. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.08.019
• 作为产物：
  描述：

  在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以0.39 g的产率得到6-(5'-Methyl-2'-hydroxyphenyl)-2-formyl-pyridine
  参考文献：
  名称：

  Use of Suzuki cross-coupling as a route to 2-phenoxy-6-iminopyridines and chiral 2-phenoxy-6-(methanamino)pyridines

  摘要：

  The anisyl boronic acids, 2-OMe-3-R-2-5-R-1-C6H2B(OH)(2) (R-1=R-2=H (a); R-1=H, R-2=Ph (b); R-1=Me, R-2=H (c); R-1=Cl, R-2=H (d); R-1=t-Bu, R-2=H (e)), have been employed in Suzuki cross-coupling reactions with either 2-bromo-6-formylpyridine (1) or 2-bromo-6-acetylpyridine (11) generating, following a facile deprotection step, the 2-phenoxy-6-carbonylpyridines, 2-(2'-OH-3'-R-2-5'-R-1-C6H2)-6-(CH=O)C5H3N (R-1=R-2=H (1a); R-1=Me, R-2=H (1c); R-1=Cl, R-2=H (1d); R-1=t-Bu, R-2=H (1e)) and 2-(2'-OH-3'-R-2-5'-R-1-C6H2)-6-(CMe=O)C5H3N (R-1=R-2=H (2a); R-1=H, R-2=Ph (2b)). Condensation reactions of 1 and 2 with 2,6-diisopropylaniline proceed smoothly to give the 2-phenoxy-6-iminopyridines, 2-(2'-OH-3'-R-2-5'-R-1-C6H2)-6-{CH=N(2,6-i-Pr2C6H3)}C5H3N (R-1=R-2=H (3a); R-1=Me, R-2=H (3c); R-1=Cl, R-2=H (3d); R-1=t-Bu, R-2=H (3e)) and 2-(2'-OH-3'-R-2-5'-R-2-C6H2)-6-{CMe=N(2,6-i-Pr2C6H3)}C5H3N (R-1=H, R-2=Ph (4a), R-1=H, R-2=Ph (4b)). Reduction of the imino unit (and concomitant C-C bond formation) in 3 can be achieved by treatment with trimethylaluminium or methyllithium which, following hydrolysis, furnishes the racemic chiral 2-phenoxy-6-(methanamino)pyridines, 2-(2'-OH-3'-R-2-5'-R-1-C6H2)-6-{CHMe-NH(2,6-i-Pr2C6H3)}C5H3N {R-1=R-2=H (5a); R-1=Me, R-2=H (5c); R-1=Cl, R-2=H (5d); R-1=t-Bu, R-2=H (5e)). This work represents a straightforward and rapid synthetic route to libraries of sterically and electronically variable phenoxy-substituted imino- and methanamino-pyridines, which are expected to act as useful ligands or proligands for late and early transition metal-mediated alkene polymerisation catalysis. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.08.019

文献信息

• Catalyst Compounds And Use Thereof
  申请人：Giesbrecht Garth R.

  公开号：US20080182952A1

  公开（公告）日：2008-07-31

  This invention relates to a transition metal catalyst compound represented by the structure: wherein: each X is, independently, a hydride, a halogen, a hydrocarbyl, a substituted hydrocarbyl, a halocarbyl, or a substituted halocarbyl; w is 2; each R 1 , R 2 , R 3 , and R 4 is, independently, a hydrogen, a hydrocarbyl, a substituted hydrocarbyl, a halocarbyl, a substituted halocarbyl, a halogen, an alkoxide, a sulfide, an amide, a phosphide, a silyl or another anionic heteroatom-containing group, or independently, may join together to form a C 4 to C 62 cyclic or polycyclic ring structure; each R 5 , R 6 , and R 7 is, independently, a hydrogen, a hydrocarbyl, a substituted hydrocarbyl, a halocarbyl, a substituted halocarbyl, a halogen, an alkoxide, a sulfide, an amide, a phosphide, a silyl or another anionic heteroatom-containing group, or independently, may join together to form a C 4 to C 62 cyclic or polycyclic ring structure; each R 8 and R 9 , is, independently, a hydrogen, a hydrocarbyl, a substituted hydrocarbyl, a halocarbyl, or a substituted halocarbyl, a halogen, an alkoxide, a sulfide, an amide, a phosphide, a silyl or another anionic heteroatom-containing group; R 10 is a hydrogen, a hydrocarbyl, a substituted hydrocarbyl, a halocarbyl, or a substituted halocarbyl, a halogen, an alkoxide, a sulfide, an amide, a phosphide, a silyl or another anionic heteroatom-containing group; x is 1, 2, 3 or 4; L is a neutral ligand bonded to M; M is titanium, zirconium or hafnium; and m is 0, 1 or 2.

  本发明涉及一种过渡金属催化剂化合物，其结构表示为：其中：每个X独立地是氢化物、卤素、烃基、取代烃基、卤代烃基或取代卤代烃基；w为2；每个R1、R2、R3和R4独立地是氢、烃基、取代烃基、卤代烃基、取代卤代烃基、卤素、醇酸盐、硫化物、酰胺、磷化物、硅基或另一种带负离子杂原子的基团，或独立地结合形成C4到C62的环状或多环结构；每个R5、R6和R7独立地是氢、烃基、取代烃基、卤代烃基、取代卤代烃基、卤素、醇酸盐、硫化物、酰胺、磷化物、硅基或另一种带负离子杂原子的基团，或独立地结合形成C4到C62的环状或多环结构；每个R8和R9独立地是氢、烃基、取代烃基、卤代烃基、取代卤代烃基、卤素、醇酸盐、硫化物、酰胺、磷化物、硅基或另一种带负离子杂原子的基团；R10是氢、烃基、取代烃基、卤代烃基、取代卤代烃基、卤素、醇酸盐、硫化物、酰胺、磷化物、硅基或另一种带负离子杂原子的基团；x为1、2、3或4；L是与M配位的中性配体；M是钛、锆或铪；m为0、1或2。
• Catalyst compounds are use thereof
  申请人：ExxonMobile Chemical Patents Inc.

  公开号：US07767773B2

  公开（公告）日：2010-08-03

  This invention relates to a transition metal catalyst compound represented by the structure: wherein: each X is, independently, a hydride, a halogen, a hydrocarbyl, a substituted hydrocarbyl, a halocarbyl, or a substituted halocarbyl; w is 2; each R1, R2, R3, and R4 is, independently, a hydrogen, a hydrocarbyl, a substituted hydrocarbyl, a halocarbyl, a substituted halocarbyl, a halogen, an alkoxide, a sulfide, an amide, a phosphide, a silyl or another anionic heteroatom-containing group, or independently, may join together to form a C4 to C62 cyclic or polycyclic ring structure; each R5, R6, and R7 is, independently, a hydrogen, a hydrocarbyl, a substituted hydrocarbyl, a halocarbyl, a substituted halocarbyl, a halogen, an alkoxide, a sulfide, an amide, a phosphide, a silyl or another anionic heteroatom-containing group, or independently, may join together to form a C4 to C62 cyclic or polycyclic ring structure; each R8 and R9, is, independently, a hydrogen, a hydrocarbyl, a substituted hydrocarbyl, a halocarbyl, or a substituted halocarbyl, a halogen, an alkoxide, a sulfide, an amide, a phosphide, a silyl or another anionic heteroatom-containing group; R10 is a hydrogen, a hydrocarbyl, a substituted hydrocarbyl, a halocarbyl, or a substituted halocarbyl, a halogen, an alkoxide, a sulfide, an amide, a phosphide, a silyl or another anionic heteroatom-containing group; x is 1, 2, 3 or 4; L is a neutral ligand bonded to M; M is titanium, zirconium or hafnium; and m is 0, 1 or 2.

  本发明涉及一种由以下结构表示的过渡金属催化剂化合物：其中：每个X独立地是氢化物、卤素、烃基、取代烃基、卤代烃基或取代卤代烃基；w为2；每个R1、R2、R3和R4独立地是氢、烃基、取代烃基、卤代烃基、取代卤代烃基、卤素、醇酸盐、硫化物、酰胺、磷化物、硅烷或另一个带有阴离子杂原子的基团，或独立地可以结合形成C4到C62的环状或多环状环结构；每个R5、R6和R7独立地是氢、烃基、取代烃基、卤代烃基、取代卤代烃基、卤素、醇酸盐、硫化物、酰胺、磷化物、硅烷或另一个带有阴离子杂原子的基团，或独立地可以结合形成C4到C62的环状或多环状环结构；每个R8和R9独立地是氢、烃基、取代烃基、卤代烃基、取代卤代烃基、卤素、醇酸盐、硫化物、酰胺、磷化物、硅烷或另一个带有阴离子杂原子的基团；R10是氢、烃基、取代烃基、卤代烃基、取代卤代烃基、卤素、醇酸盐、硫化物、酰胺、磷化物、硅烷或另一个带有阴离子杂原子的基团；x为1、2、3或4；L是与M结合的中性配体；M为钛、锆或铪；m为0、1或2。
• Catalyst compounds and use thereof
  申请人：ExxonMobil Chemical Patents Inc.

  公开号：EP2112173A1

  公开（公告）日：2009-10-28

  This invention relates to a transition metal catalyst compound represented by the structure: wherein: each X is, independently, a hydride, a halogen, a hydrocarbyl, a substituted hydrocarbyl, a halocarbyl, or a substituted halocarbyl; w is 2; each R1, R2, R3, and R4 is, independently, a hydrogen, a hydrocarbyl, a substituted hydrocarbyl, a halocarbyl, a substituted halocarbyl, a halogen, an alkoxide, a sulfide, an amide, a phosphide, a silyl or another anionic heteroatom-containing group, or independently, may join together to form a C4 to C62 cyclic or polycyclic ring structure; each R5, R6, and R7 is, independently, a hydrogen, a hydrocarbyl, a substituted hydrocarbyl, a halocarbyl, a substituted halocarbyl, a halogen, an alkoxide, a sulfide, an amide, a phosphide, a silyl or another anionic heteroatom-containing group, or independently, may join together to form a C4 to C62 cyclic or polycyclic ring structure; each R8 and R9, is, independently, a hydrogen, a hydrocarbyl, a substituted hydrocarbyl, a halocarbyl, or a substituted halocarbyl, a halogen, an alkoxide, a sulfide, an amide, a phosphide, a silyl or another anionic heteroatom-containing group; R10 is a hydrogen, a hydrocarbyl, a substituted hydrocarbyl, a halocarbyl, or a substituted halocarbyl, a halogen, an alkoxide, a sulfide, an amide, a phosphide, a silyl or another anionic heteroatom-containing group; x is 1, 2, 3 or 4; L is a neutral ligand bonded to M; M is titanium, zirconium or hafnium; and m is 0, 1 or 2.

  本发明涉及一种由以下结构表示的过渡金属催化剂化合物： 其中每个 X 独立地是氢化物、卤素、烃基、取代的烃基、卤代羰基或取代的卤代羰基； w 是 2；每个 R1、R2、R3 和 R4 独立地是氢、烃基、取代的烃基、卤代羰基、取代的卤代羰基、卤素、烷氧基、硫化物、酰胺、膦化物、硅烷基或另一种含阴离子杂原子的基团，或独立地可连接在一起形成 C4 至 C62 的环状或多环状结构；每个 R5、R6 和 R7 独立地是氢、烃基、取代的烃基、卤代羰基、取代的卤代羰基、卤素、烷氧基、硫化物、酰胺、磷化物、硅烷基或其他含阴离子杂原子的基团，或可独立地连接在一起形成 C4 至 C62 的环状或多环状结构；每个 R8 和 R9 独立地是氢、烃基、取代的烃基、卤代羰基或取代的卤代羰基、卤素、烷氧基、硫化物、酰胺、磷化物、硅烷基或其他含阴离子杂原子的基团；R10 是氢、烃基、取代的烃基、卤代羰基或取代的卤代羰基、卤素、烷氧基、硫化物、酰胺、磷化物、硅烷基或另一种含阴离子杂原子的基团；x 是 1、2、3 或 4；L 是与 M 键合的中性配体；M 是钛、锆或铪；以及 m 是 0、1 或 2。
• CATALYST COMPOUNDS AND USE THEREOF
  申请人：ExxonMobil Chemical Patents Inc.

  公开号：EP2231715A1

  公开（公告）日：2010-09-29
• US7767773B2
  申请人：——

  公开号：US7767773B2

  公开（公告）日：2010-08-03