5-methyl-3-hexynoic acid | 942283-77-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 5-methyl-3-hexynoic acid
• 英文别名: 5-Methylhex-3-ynoic acid
• CAS: 942283-77-4
• 化学式: C₇H₁₀O₂
• 分子量: 126.155
• InChiKey: GPABEWPBBKOULI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  一氧化碳 、 5-methyl-3-hexynoic acid 在 dicarbonylacetylacetonato rhodium (I) 、 混旋樟脑磺酸 、 N-{6-[bis-(3’,5’-bis(trifluoromethyl)phenyl)phosphanyl]pyridine-2-carbonyl}guanidine 、 氢气 作用下， 以 1,2-二氯乙烷 为溶剂， 55.0 ℃ 、600.01 kPa 条件下， 反应 20.17h， 生成 3-formyl-5-methylhex-3-enoic acid 、 4-Formyl-5-methylhexanoic acid
  参考文献：
  名称：

  使用超分子催化剂对内部炔烃进行串联区域选择性加氢甲酰化加氢

  摘要：

  基于通过引入吸电子基团提高膦配体的π-受体能力的策略，设计了具有酰基胍基功能的新的超分子配体。通过应用这种新颖的催化系统，发现了用羧酸官能化的不对称内部炔烃进行Rh催化加氢甲酰化-加氢的通用方案，可提供具有高区域选择性和化学选择性的脂族醛。对照实验证实了类似酶的超分子催化剂的作用方式。

  DOI：

  10.1002/anie.201809073
• 作为产物：
  描述：

  5-methylhex-3-yn-1-ol 在 Jones reagent 作用下， 以 丙酮 为溶剂， 反应 3.0h， 以56%的产率得到5-methyl-3-hexynoic acid
  参考文献：
  名称：

  使用超分子催化剂对内部炔烃进行串联区域选择性加氢甲酰化加氢

  摘要：

  基于通过引入吸电子基团提高膦配体的π-受体能力的策略，设计了具有酰基胍基功能的新的超分子配体。通过应用这种新颖的催化系统，发现了用羧酸官能化的不对称内部炔烃进行Rh催化加氢甲酰化-加氢的通用方案，可提供具有高区域选择性和化学选择性的脂族醛。对照实验证实了类似酶的超分子催化剂的作用方式。

  DOI：

  10.1002/anie.201809073

文献信息

• Asymmetric Olefin Isomerization of Butenolides via Proton Transfer Catalysis by an Organic Molecule
  作者：Yongwei Wu、Ravi P. Singh、Li Deng

  DOI：10.1021/ja205674x

  日期：2011.8.17

  general olefin isomerization was realized via biomimetic proton transfer catalysis with a new chiral organic catalyst. A broad range of mono- and disubstituted β,γ-unsaturated butenolides were transformed into the corresponding chiral α,β-unsaturated butenolides in high enantioselectivity and yield in the presence of as low as 0.5 mol % catalyst. Mechanistic studies have revealed the protonation as the

  通过使用新型手性有机催化剂的仿生质子转移催化，实现了前所未有的对映选择性和通用烯烃异构化。在低至 0.5 mol% 的催化剂存在下，多种单取代和双取代的 β,γ-不饱和丁烯内酯以高对映选择性和产率转化为相应的手性 α,β-不饱和丁烯内酯。机理研究表明质子化是决定速率的步骤。
• [EN] 4-(4-PYRIDINYL)-BENZAMIDES AND THEIR USE AS ROCK ACTIVITY MODULATORS<br/>[FR] COMPOSÉS 4-(4-PYRIMIDYL)-BENZAMIDES ET UTILISATION DE CEUX-CI COMME MODULATEURS DE L'ACTIVITÉ DE KINASES RHO (ROCK)
  申请人：ABBOTT GMBH & CO KG

  公开号：WO2009027392A1

  公开（公告）日：2009-03-05

  The present invention relates to novel 4-(4-pyridyl)-benzamides of the formula (I). The compounds I possess valuable therapeutic properties and are suitable, in particular, for treating diseases that respond to modulation of Rho kinases (ROCKs). R1 and R2 are, independently of each other, hydrogen, hydroxy, cyano, C1-C8-alkyl, C1- C8-haloalkyl, C1-C8-alkoxy or C1-C8-haloalkoxy; R3, R4, R5 and R6 are, independently of each other, hydrogen, hydroxy, halogen, cyano, C1-C8-alkyl, C1-C8-haloalkyl, C1-C8-alkoxy, C1-C8-haloalkoxy, amino, C1-C8-alkylamino or di-(C1-C8-alkyl)-amino; R7 is hydrogen, C1-C8-alkyl, C1-C8-haloalkyl, aryl or aryl-C1-C8-alkyl; R8 is a group of the formula -X-W, where X is a single bond, C1-C4-alkylene or C1-C4-alkylene-O-, where the alkylene group in the three last-mentioned radicals may be linear or branched and may be partly or fully halogenated and/or may be substituted by a hydroxyl group and/or may be interrupted by an oxygen atom; and W is a cyclic radical selected from phenyl and a 5- or 6-membered saturated, partly unsaturated or aromatic heterocyclic ring which contains as ring members 1, 2 or 3 heteroatoms selected from O, S and N and optionally 1 or 2 carbonyl groups; R9 is a group of the formula -Y-Z, where Z is hydrogen, halogen, OR11, NR12R13, S(O)m-R14, phenyl which may carry 1, 2, 3 or 4 substituents R15 or a 5- or 6-membered saturated, partly unsaturated or aromatic heterocyclic ring; and Y is linear or branched C1C4-alkylene which may be partly or fully halogenated and/or may be substituted by a hydroxyl group and/or a phenyl ring; or, in case Z is phenyl or the 5- or 6-membered heterocyclic ring as defined above, Y can also be a single bond.

  本发明涉及公式（I）的新型4-(4-吡啶基)-苯甲酰胺。化合物I具有有价值的治疗性能，并且特别适用于治疗对Rho激酶（ROCKs）调节产生反应的疾病。R1和R2分别为氢、羟基、氰基、C1-C8-烷基、C1-C8-卤代烷基、C1-C8-烷氧基或C1-C8-卤代烷氧基；R3、R4、R5和R6分别为氢、羟基、卤素、氰基、C1-C8-烷基、C1-C8-卤代烷基、C1-C8-烷氧基、C1-C8-卤代烷氧基、氨基、C1-C8-烷基氨基或二(C1-C8-烷基)-氨基；R7为氢、C1-C8-烷基、C1-C8-卤代烷基、芳基或芳基-C1-C8-烷基；R8为-X-W的基团，其中X为单键、C1-C4-烷基或C1-C4-烷基-O-，在上述最后三个基团中的烷基可以是直链或支链，可以部分或完全卤代，和/或可以被羟基取代，和/或可以被氧原子打断；W为选择自苯基和含有1、2或3个来自O、S和N的杂原子以及可选地包含1或2个羰基的5-或6-成员饱和、部分不饱和或芳香杂环的环基；R9为-Y-Z的基团，其中Z为氢、卤素、OR11、NR12R13、S(O)m-R14、可能携带1、2、3或4个取代基R15的苯基或5-或6-成员饱和、部分不饱和或芳香杂环的环基；Y为线性或支链的C1-C4-烷基，可以部分或完全卤代，和/或可以被羟基取代，和/或可以是苯环；或者，如果Z为苯基或上述定义的5-或6-成员杂环环，Y也可以是单键。
• 4-(4-PYRIDINYL)-BENZAMIDES AND THEIR USE AS ROCK ACTIVITY MODULATORS
  申请人：Mack Helmut

  公开号：US20100273828A1

  公开（公告）日：2010-10-28

  The present invention relates to novel 4-(4-pyridyl)-benzamides of the formula (I). The compounds I possess valuable therapeutic properties and are suitable, in particular, for treating diseases that respond to modulation of Rho kinases (ROCKs). R 1 and R 2 are, independently of each other, hydrogen, hydroxy, cyano, C 1 -C 8 -alkyl, C 1 -C 8 -haloalkyl, C 1 -C 8 -alkoxy or C 1 -C 8 -haloalkoxy; R 3 , R 4 , R 5 and R 6 are, independently of each other, hydrogen, hydroxy, halogen, cyano, C 1 -C 8 -alkyl, C 1 -C 8 -haloalkyl, C 1 -C 8 -alkoxy, C 1 -C 8 -haloalkoxy, amino, C 1 -C 8 -alkylamino or di-(C 1 -C 8 -alkyl)-amino; R 7 is hydrogen, C 1 -C 8 -alkyl, C 1 -C 8 -haloalkyl, aryl or aryl-C 1 -C 8 -alkyl; R 8 is a group of the formula —X—W, where X is a single bond, C 1 -C 4 -alkylene or C 1 -C 4 -alkylene-O—, where the alkylene group in the three last-mentioned radicals may be linear or branched and may be partly or fully halogenated and/or may be substituted by a hydroxyl group and/or may be interrupted by an oxygen atom; and W is a cyclic radical selected from phenyl and a 5- or 6-membered saturated, partly unsaturated or aromatic heterocyclic ring which contains as ring members 1, 2 or 3 heteroatoms selected from O, S and N and optionally 1 or 2 carbonyl groups; R 9 is a group of the formula —Y—Z, where Z is hydrogen, halogen, OR 11 , NR 12 R 13 , S(O) m —R 14 , phenyl which may carry 1, 2, 3 or 4 substituents R 15 or a 5- or 6-membered saturated, partly unsaturated or aromatic heterocyclic ring; and Y is linear or branched C 1 C 4 -alkylene which may be partly or fully halogenated and/or may be substituted by a hydroxyl group and/or a phenyl ring; or, in case Z is phenyl or the 5- or 6-membered heterocyclic ring as defined above, Y can also be a single bond.

  本发明涉及式(I)的新型4-(4-吡啶基)-苯甲酰胺化合物。化合物I具有有价值的治疗性能，特别适用于治疗对Rho激酶（ROCKs）调节有反应的疾病。其中，R1和R2分别独立地为氢、羟基、氰基、C1-C8烷基、C1-C8卤代烷基、C1-C8烷氧基或C1-C8卤代烷氧基；R3、R4、R5和R6分别独立地为氢、羟基、卤素、氰基、C1-C8烷基、C1-C8卤代烷基、C1-C8烷氧基、C1-C8卤代烷氧基、氨基、C1-C8烷基氨基或二-(C1-C8烷基)-氨基；R7为氢、C1-C8烷基、C1-C8卤代烷基、芳基或芳基-C1-C8烷基；R8为公式-X-W的基团，其中X为单键、C1-C4-烷基或C1-C4-烷基-O-，其中上述三种基团中的烷基基团可以是直链或支链并且可以部分或完全卤代和/或可以被羟基取代和/或可以被氧原子中断；W为从苯基和一个含有1、2或3个从O、S和N中选择的杂原子和可选地1或2个羰基的5-或6-成员饱和、部分不饱和或芳香杂环环中选择的环状基团；R9为公式-Y-Z的基团，其中Z为氢、卤素、OR11、NR12R13、S(O)m-R14、可以携带1、2、3或4个取代基R15的苯基或5-或6-成员饱和、部分不饱和或芳香杂环环；Y为线性或支链的C1-C4-烷基，可以部分或完全卤代和/或可以被羟基和/或苯环取代；或者，如果Z为上述定义的苯基或5-或6-成员杂环环，则Y也可以是单键。
• One-Step Asymmetric Construction of 1,4-Stereocenters via Tandem Mannich-Isomerization Reactions Mediated by a Dual-Functional Betaine Catalyst
  作者：Yu Deng、Xiaohuo Shi、Guangfa Shi、Xingyu Lu、Jisheng Luo、Li Deng

  DOI：10.1021/jacsau.2c00465

  日期：2022.12.26

  Mannich-isomerization reaction that allows the direct construction of 1,4-stereocenters in a highly stereoselective manner. This asymmetric transformation demonstrated the potential of a tandem nucleophilic addition-isomerization reaction as a broadly useful strategy for the efficient construction of 1,4-stereocenters. Notably, this tandem reaction was mediated by a single chiral betaine as a dual-functional

  包含不相邻立体中心的手性基序的构建是一项重大挑战，因为它们通常是使用不同的手性催化剂在不同的步骤中构建的。因此，开发简化此类复杂基序构造的新策略已成为不对称合成的主要焦点。我们在此报告了前所未有的不对称串联曼尼希异构化反应，该反应允许以高度立体选择性的方式直接构建 1,4-立体中心。这种不对称转化证明了串联亲核加成异构化反应作为有效构建 1,4-立体中心的广泛有用策略的潜力。值得注意的是，这种串联反应是由作为双功能催化剂的单一手性甜菜碱介导的，
• Fused-ring quinone-substituted polynorbornene, electrode active material and secondary battery
  申请人：WASEDA UNIVERSITY

  公开号：US10164258B2

  公开（公告）日：2018-12-25

  A fused-ring quinone-substituted polynorbornene has recurring units of formula (1) and/or (2) below. In formulas (1) and (2), A1 is independently a substituent of formula (3) or (4) below, n is an integer from 1 to 6, and A2 is a substituent of formula (5) or (6) below. In formulas (3) to (6), each X is independently a single bond or a divalent group, and Ar1 and Ar2 are each independently an aromatic hydrocarbon ring or an oxygen atom or sulfur atom-containing aromatic heterocycle that forms together with two carbon atoms on a benzoquinone skeleton. This polymer has charge-storing properties and, when used as an electrode active material, is capable of providing a high-performance battery possessing high capacity, high rate characteristics and high cycle characteristics.

  融合环醌代聚降冰片烯具有下式（1）和/或（2）的重复单元。 在式(1)和(2)中，A1 独立地是下式(3)或(4)的取代基，n 是 1 至 6 的整数，A2 是下式(5)或(6)的取代基。 在式(3)至式(6)中，每个 X 独立地为单键或二价基团，Ar1 和 Ar2 独立地为芳香烃环或与苯醌骨架上的两个碳原子共同形成的含氧原子或硫原子的芳香杂环。这种聚合物具有电荷储存特性，用作电极活性材料时，能够提供具有高容量、高倍率特性和高循环特性的高性能电池。