5-((diethylamino)methyl)-2-hydroxybenzaldehyde | 57119-43-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-((diethylamino)methyl)-2-hydroxybenzaldehyde
• 英文别名: 5-diethylaminomethylsalicylaldehyde；5-(diethylaminomethyl)-2-hydroxybenzaldehyde
• CAS: 57119-43-4
• 化学式: C₁₂H₁₇NO₂
• 分子量: 207.272
• InChiKey: ZLIHMWGGIRNLBU-UHFFFAOYSA-N

物化性质

• 沸点：
  291.3±30.0 °C(Predicted)
• 密度：
  1.095±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-((diethylamino)methyl)-2-hydroxybenzaldehyde 在 二乙胺 、 三乙胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 3-(4-(4-chlorophenyl)thiazol-2-yl)-6-((diethylamino)methyl)-2H-chromen-2-one
  参考文献：
  名称：

  连接到噻唑单元的新型双（色烯）和双（苯并[f]色烯）的有效合成和表征

  摘要：

  与色烯或苯并 [f] 色烯单元相连的新硫代酰胺被视为本研究的关键合成子。这些硫代碳酰胺以良好的收率通过...的环缩合反应制备。

  DOI：

  10.1080/00397911.2020.1846748
• 作为产物：
  描述：

  2-羟基-5-氯甲基苯甲醛 、 二乙胺 以 乙腈 为溶剂， 以99%的产率得到5-((diethylamino)methyl)-2-hydroxybenzaldehyde
  参考文献：
  名称：

  连接到噻唑单元的新型双（色烯）和双（苯并[f]色烯）的有效合成和表征

  摘要：

  与色烯或苯并 [f] 色烯单元相连的新硫代酰胺被视为本研究的关键合成子。这些硫代碳酰胺以良好的收率通过...的环缩合反应制备。

  DOI：

  10.1080/00397911.2020.1846748

文献信息

• [EN] SYNTHESIS OF CYCLIC CARBONATES<br/>[FR] SYNTHÈSE DE CARBONATES CYCLIQUES
  申请人：UNIV NEWCASTLE

  公开号：WO2009109765A1

  公开（公告）日：2009-09-11

  A dimeric aluminium(salen) catalyst of formula I: herein: Y-Q is CRC1=N or CRC1RC2-NRN1, where RC1, RC2 and RN1 are independently selected from H, halo, optionally substituted C1-20 alkyl, optionally substituted C5-20 aryl, ether and nitro; each of the substituents R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, and R16, is independently selected from H, halo, optionally substituted C1-20 alkyl, optionally substituted C5-20 aryl, optionally substituted C3-20 heterocyclyl, ether and nitro; X1 and X2 are independently either (i) a C2-5 alkylene chain, which is optionally substituted by one or more groups selected from C1-4 alkyl and C5-7 aryl, or a C1-3 bisoxyalkylene chain, which is optionally substituted by one or more groups selected from C1-4 alkyl and C5-7 aryl or (ii) represent a divalent group selected from C5-7 arylene, C5-7 cyclic alkylene and C3-7 heterocyclylene, which may be optionally substituted; (i) (a) at least one of R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, and R16 is selected from L-A, where L is a single bond or a C1-10 alkylene group and A is an ammonium group paired with a counterion selected from Cl, Br and I; and/or (b) at least one of X1 and X2 is a divalent C3-7 heterocyclene group, containing a ring atom which is a quaternary nitrogen atom paired with a counterion selected from Cl, Br and I; and/or (c) at least one of X1 and X2 is a C2-5 alkylene chain or a C1-3 bisoxyalkylene chain, substituted by a group -Q-L-A, where Q is either -C(=O)-O-, -C(=O)-NH-, or a single bond; and/or (ii) (a) one of R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, and R16 is L-A', where L is as defined above and A' is a ammonium linking group bound to a solid support and paired with a counterion selected from Cl, Br and I; or (b) one of X1 and X2 is a divalent C3-7 heterocyclene group, containing a ring atom which is a quaternary nitrogen forming part of an ammonium linking group bound to a solid support and paired with a counterion selected from Cl, Br and I; or (c) one of X1 and X2 is a C2-5 alkylene chain or a C1-3 bisoxyalkylene chain, substituted by a group -Q-L-A'.

  一种二聚铝（salen）催化剂的化学式I：在此处：Y-Q是CRC1=N或CRC1RC2-NRN1，其中RC1、RC2和RN1分别独立选择自H、卤素、可选择性取代的C1-20烷基、可选择性取代的C5-20芳基、醚和硝基；R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14、R15和R16中的每一个取代基都是独立选择自H、卤素、可选择性取代的C1-20烷基、可选择性取代的C5-20芳基、可选择性取代的C3-20杂环烷基、醚和硝基；X1和X2独立地是（i）C2-5烷基链，可选择性地通过一个或多个来自C1-4烷基和C5-7芳基的基团取代，或者是C1-3双氧烷基链，可选择性地通过一个或多个来自C1-4烷基和C5-7芳基的基团取代；或者（ii）代表可选择性取代的C5-7芳基、C5-7环烷基和C3-7杂环烷基中选取的二价基团；（i）（a）R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14、R15和R16中至少一个选择自L-A，其中L是单键或C1-10烷基基团，A是与Cl、Br和I中选取的对离子配对的铵基；和/或（b）X1和X2中至少一个是含有一个环原子为季氮原子的三价C3-7杂环烷基团，配对的对离子为Cl、Br和I；和/或（c）X1和X2中至少一个是由基团-Q-L-A取代的C2-5烷基链或C1-3双氧烷基链，其中Q是-E(=O)-O-、-E(=O)-NH-或单键；和/或（ii）（a）R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14、R15和R16中的一个是L-A'，其中L如上所定义，A'是与Cl、Br和I中选取的对离子配对的铵基固定在固体支撑上；或者（b）X1和X2中的一个是含有一个环原子为季氮原子构成铵基固定在固体支撑上的三价C3-7杂环烷基团，配对的对离子为Cl、Br和I；或者（c）X1和X2中的一个是由基团-Q-L-A'取代的C2-5烷基链或C1-3双氧烷基链。
• Reducing the Cost of Production of Bimetallic Aluminium Catalysts for the Synthesis of Cyclic Carbonates
  作者：Michael North、Carl Young

  DOI：10.1002/cssc.201100239

  日期：2011.11.18

  Bimetallic aluminium complexes of general formula [(salen)Al]2O or [(acen)Al]2O catalyse the formation of cyclic carbonates from carbon dioxide and terminal epoxides under exceptionally mild reaction conditions. To improve the potential for industrial scale application of these catalysts, the cost of their production has been evaluated and reduced significantly by optimization of the synthesis, including

  通式[（salen）Al] 2 O或[（acen）Al] 2的双金属铝配合物O在异常温和的反应条件下催化由二氧化碳和末端环氧化物形成环状碳酸酯。为了提高这些催化剂在工业规模上的应用潜力，已经通过优化合成方法，包括用较便宜的替代品替代最昂贵的化学药品，评估并显着降低了其生产成本。最大的成本节省与原位三乙氧基铝的形成有关，这使生产催化剂所需的化学药品成本降低了49–87％。通过避免使用四丁基溴化铵和乙腈，可以进一步节省成本，从而使总体成本节省68-93％。
• SYNTEHSIS OF CYCLIC CARBONATES
  申请人：UNIVERSITY OF NEW CASTLE UPON TYNE

  公开号：US20130317237A1

  公开（公告）日：2013-11-28

  A dimeric aluminium(salen) catalyst of formula I: wherein: (a) at least one R group is selected from L-A, and/or (b) at least one of X group is a divalent C3-7 heterocyclene group, containing a ring atom which is a quaternary nitrogen atom paired with a counterion selected from Cl, Br and I; and/or (c) at least one X group is a C2-5 alkylene chain or a C1-3 bisoxyalkylene chain, substituted by a group -Q-L-A; and/or (ii) (a) one R group is L-A′, or (b) one X group is a divalent C3-7 heterocyclene group, containing a ring atom which is a quaternary nitrogen forming part of an ammonium linking group bound to a solid support and paired with a counterion selected from Cl, Br and I; or (c) one X group is a C2-5 alkylene chain or a C1-3 bisoxyalkylene chain, substituted by a group -Q-L-A′.

  式I的二聚铝(salen)催化剂: 其中: (a) 至少一个R基团选自L-A，和/或 (b) 至少一个X基团是一个二价C3-7杂环烃基团，含有一个环原子，该环原子是一个季铵氮原子，与Cl、Br和I中选择的一个计数离子成对; 和/或 (c) 至少一个X基团是一个C2-5烷基链或C1-3双氧烷基链，被一个-Q-L-A基团取代; 和/或 (ii) (a) 一个R基团是L-A'，或(b) 一个X基团是一个二价C3-7杂环烃基团，含有一个环原子，该环原子是一个与固体支撑物相结合的铵连接基团的季铵氮原子，并与Cl、Br和I中选择的一个计数离子成对; 或(c) 一个X基团是一个C2-5烷基链或C1-3双氧烷基链，被一个-Q-L-A'基团取代。
• Synthesis of cyclic carbonates
  申请人：UNIVERSITY OF NEW CASTLE UPON TYNE

  公开号：US09273024B2

  公开（公告）日：2016-03-01

  A dimeric aluminum(salen) catalyst of formula I: wherein: (a) at least one R group is selected from L-A, and/or (b) at least one of X group is a divalent C3-7 heterocyclene group, containing a ring atom which is a quaternary nitrogen atom paired with a counterion selected from Cl, Br and I; and/or (c) at least one X group is a C2-5 alkylene chain or a C1-3 bisoxyalkylene chain, substituted by a group -Q-L-A; and/or (ii) (a) one R group is L-A′, or (b) one X group is a divalent C3-7 heterocyclene group, containing a ring atom which is a quaternary nitrogen forming part of an ammonium linking group bound to a solid support and paired with a counterion selected from Cl, Br and I; or (c) one X group is a C2-5 alkylene chain or a C1-3 bisoxyalkylene chain, substituted by a group -Q-L-A′.

  化学式为I的二聚铝(salen)催化剂，其中：(a)至少一个R基团选自L-A，和/或(b)至少一个X基团是含有一个环原子的二价C3-7杂环基团，该环原子是与Cl、Br和I中选择的一个对离子成对的季铵氮原子；和/或(c)至少一个X基团是C2-5烷基链或C1-3双氧烷基链，被-Q-L-A基团取代；和/或(ii)(a)一个R基团是L-A'，或(b)一个X基团是含有一个环原子的二价C3-7杂环基团，该环原子是与固体支撑物结合的季铵连接基团的一部分，与Cl、Br和I中选择的一个对离子成对；或(c)一个X基团是C2-5烷基链或C1-3双氧烷基链，被-Q-L-A'基团取代。
• SYNTHESIS OF CYCLIC CARBONATES
  申请人：North Michael

  公开号：US20110015409A1

  公开（公告）日：2011-01-20

  A dimeric aluminium(salen) catalyst of formula I: wherein: Y-Q is CR C1 ═N or CR C1 R C2 —NR N1 , where R C1 , R C2 and R N1 are independently selected from H, halo, optionally substituted C 1-20 alkyl, optionally substituted C 5-20 aryl, ether and nitro; each of the substituents R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , and R 16 , is independently selected from H, halo, optionally substituted C 1-20 alkyl, optionally substituted C 5-20 aryl, optionally substituted C 3-20 heterocyclyl, ether and nitro; X 1 and X 2 are independently either (i) a C 2-5 alkylene chain, which is optionally substituted by one or more groups selected from C 1-4 alkyl and C 5-7 aryl, or a C 1-3 bisoxyalkylene chain, which is optionally substituted by one or more groups selected from C 1-4 alkyl and C 5-7 aryl or (ii) represent a divalent group selected from C 5-7 arylene, C 5-7 cyclic alkylene and C 3-7 heterocyclylene, which may be optionally substituted; (i) (a) at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , and R 16 is selected from L-A, where L is a single bond or a C 1-10 alkylene group and A is an ammonium group paired with a counterion selected from Cl, Br and I; and/or (b) at least one of X 1 and X 2 is a divalent C 3-7 heterocyclene group, containing a ring atom which is a quaternary nitrogen atom paired with a counterion selected from Cl, Br and I; and/or (c) at least one of X 1 and X 2 is a C 2-5 alkylene chain or a C 1-3 bisoxyalkylene chain, substituted by a group -Q-L-A, where Q is either —C(═O)—O—, —C(═O)—NH—, or a single bond; and/or (ii) (a) one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , and R 16 is L-A′, where L is as defined above and A′ is a ammonium linking group bound to a solid support and paired with a counterion selected from Cl, Br and I; or (b) one of X 1 and X 2 is a divalent C 3-7 heterocyclene group, containing a ring atom which is a quaternary nitrogen forming part of an ammonium linking group bound to a solid support and paired with a counterion selected from Cl, Br and I; or (c) one of X 1 and X 2 is a C 2-5 alkylene chain or a C 1-3 bisoxyalkylene chain, substituted by a group -Q-L-A′.

  化学式I的二聚铝(salen)催化剂：其中：Y-Q为CRC1═N或CRC1RC2—NRN1，其中RC1、RC2和RN1独立选择自H、卤素、可选取代的C1-20烷基、可选取代的C5-20芳基、醚和硝基；每个取代基R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14、R15和R16独立选择自H、卤素、可选取代的C1-20烷基、可选取代的C5-20芳基、可选取代的C3-20杂环基、醚和硝基；X1和X2独立选择自(i) C2-5烷基链，可选取自C1-4烷基和C5-7芳基中的一个或多个基团，或C1-3双氧杂烷基链，可选取自C1-4烷基和C5-7芳基中的一个或多个基团；或(ii)代表选自C5-7芳基、C5-7环烷基和C3-7杂环烷基的二价基团，可选取代；(i)(a) R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14、R15和R16中至少一个选择自L-A，其中L为单键或C1-10烷基，A为与Cl、Br和I中选择的一个对离子配对的铵基；和/或(b) X1和X2中至少一个为含有一个季铵对离子选择自Cl、Br和I的四价氮原子的C3-7杂环烷基；和/或(c) X1和X2中至少一个为被-Q-L-A取代的C2-5烷基链或C1-3双氧杂烷基链，其中Q为—C(═O)—O—、—C(═O)—NH—或单键；和/或(ii)(a) R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14、R15和R16中的一个为L-A′，其中L如上定义，A′为与Cl、Br和I中选择的一个对离子配对的铵连接基；或(b) X1和X2中的一个为含有一个季铵对离子选择自Cl、Br和I的四价氮原子的C3-7杂环烷基，形成与固体支持物相连的铵连接基；或(c) X1和X2中的一个为被-Q-L-A′取代的C2-5烷基链或C1-3双氧杂烷基链。