1-(4-methoxyphenyl)-3-methylpentane-1,4-dione | 376637-27-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-methoxyphenyl)-3-methylpentane-1,4-dione
• 英文别名: 1-(4-Methoxyphenyl)-3-methyl 1,4-pentanedione
• CAS: 376637-27-3
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: HKJXOJMWSZOHSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-methoxyphenyl)-3-methylpentane-1,4-dione 、 4-溴苯胺 在 对甲苯磺酸一水合物 作用下， 以 甲苯 为溶剂， 以24.3%的产率得到1-(4-bromophenyl)-5-(4-methoxyphenyl)-2,3-dimethyl-1H-pyrrole
  参考文献：
  名称：

  Tyrosine phosphatase inhibitors

  摘要：

  式（I）的化合物： 其中X1和X2相同或不同，每个都是主链中具有1至20个原子的键或间隔物； R1和R2中的一个是具有取代基的环基，所述取代基选自1）可选择地取代的羧基-C1-6烷氧基和2）可选择地取代的羧基-C1-6脂肪烃基，其中所述环基可选择地具有额外的取代基，另一个是可选择地取代的环基或氢原子；以及 R3、R4和R5相同或不同，每个是氢原子或取代基，或R4可以与R3或R5结合形成可选择地取代的环； 但是当R3是氢原子时，R4是氢原子且R5是甲基时，X2—R2不是4-环己基苯基；当R3是4-甲氧基苯基，R4是氢原子且R5是甲基时，X2—R2不是4-甲氧基苯基；当R1或R2是氢原子时，相邻的X1或X2不是C1-7烷基； 或其盐具有蛋白酪氨酸磷酸酶抑制作用，并且可用作糖尿病等疾病的预防或治疗剂。

  公开号：

  US20030144338A1
• 作为产物：
  描述：

  2-(2-hydroxy-2-methylcyclopropyl)-1-(4-methoxyphenyl)ethan-1-one 在 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以72%的产率得到1-(4-methoxyphenyl)-3-methylpentane-1,4-dione
  参考文献：
  名称：

  Ring-opening of tertiary cyclopropanols derived from β-diketones

  摘要：

  The ring-opening reaction of 1,2-di substituted cyclopropanols, prepared from beta-diketones, mediated by Cu(NO3)(2), p-TsOH, and NaOH is reported. The Cu(II)-mediated ring-opening of cyclopropanols gave alpha-methylene-gamma-diketones in good yields. The reaction took place at the less substituted carbon of the cyclopropanols, involving mild conditions and a simple procedure. The reaction induced by p-TsOH in CH2O2 afforded alpha-methyl-gamma-diketones as the major product with minor amounts of 8-diketones. The 2,3,5-tri substituted furans were obtained in high yields when the ring-opening reaction was mediated by p-TsOH in methanol under reflux conditions. In the presence of sodium hydroxide the reaction proceeded smoothly in preference to the formation of beta-diketones, particularly for substrates with an aromatic group on the cyclopropane. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.05.064

文献信息

• TYROSINE PHOSPHATASE INHIBITORS
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP1284260A1

  公开（公告）日：2003-02-19

  A compound of the formula (I):    wherein X1 and X2 are the same or different and each is a bond or a spacer having 1 to 20 atom(s) in the main chain;    one of R1 and R2 is a cycle group having substituent(s) selected from 1) an optionally substituted carboxy-C1-6 alkoxy group and 2) an optionally substituted carboxy-C1-6 aliphatic hydrocarbon group, wherein the cycle group optionally has additional substituent(s), and the other is an optionally substituted cycle group or a hydrogen atom; and    R3, R4 and R5 are the same or different and each is a hydrogen atom or a substituent, or R4 may link together with R3 or R5 to form an optionally substituted ring;    provided that when R3 is a hydrogen atom, R4 is a hydrogen atom and R5 is methyl, X2-R2 is not 4-cyclohexylphenyl; when R3 is 4-methoxyphenyl, R4 is a hydrogen atom and R5 is methyl, X2-R2 is not 4-methoxyphenyl; and when R1 or R2 is a hydrogen atom, the adjacent X1 or X2 is not a C1-7 alkylene; or a salt thereof exhibits a protein tyrosine phosphatase inhibitory action and is useful as a prophylactic or therapeutic agent for diabetes or the like.

  式(I)化合物： 其中 X1 和 X2 相同或不同，且各自为键或在主链中具有 1 至 20 个原子的间隔物； R1 和 R2 中的一个是具有选自 1）任选取代的羧基-C1-6 烷氧基和 2）任选取代的羧基-C1-6 脂肪族烃基的取代基的循环基团，其中循环基团任选具有附加取代基，另一个是任选取代的循环基团或氢原子；以及 R3、R4 和 R5 相同或不同，且各自为氢原子或取代基，或 R4 可与 R3 或 R5 连接形成任选取代的环； 条件是当 R3 是氢原子、R4 是氢原子且 R5 是甲基时，X2-R2 不是 4-环己基苯基；当 R3 是 4-甲氧基苯基、R4 是氢原子且 R5 是甲基时，X2-R2 不是 4-甲氧基苯基；以及当 R1 或 R2 是氢原子时，相邻的 X1 或 X2 不是 C1-7 亚烷基； 或其盐具有蛋白酪氨酸磷酸酶抑制作用，可用作糖尿病或类似疾病的预防或治疗剂。
• US6911468B2
  申请人：——

  公开号：US6911468B2

  公开（公告）日：2005-06-28
• Tyrosine phosphatase inhibitors
  申请人：——

  公开号：US20030144338A1

  公开（公告）日：2003-07-31

  A compound of the formula (I): 1 wherein X 1 and X 2 are the same or different and each is a bond or a spacer having 1 to 20 atom(s) in the main chain; one of R 1 and R 2 is a cycle group having substituent(s) selected from 1) an optionally substituted carboxy-C 1-6 alkoxy group and 2) an optionally substituted carboxy-C 1-6 aliphatic hydrocarbon group, wherein the cycle group optionally has additional substituent(s), and the other is an optionally substituted cycle group or a hydrogen atom; and R 3 , R 4 and R 5 are the same or different and each is a hydrogen atom or a substituent, or R 4 may link together with R 3 or R 5 to form an optionally substituted ring; provided that when R 3 is a hydrogen atom, R 4 is a hydrogen atom and R 5 is methyl, X 2 —R 2 is not 4-cyclohexylphenyl; when R 3 is 4-methoxyphenyl, R 4 is a hydrogen atom and R 5 is methyl, X 2 —R 2 is not 4-methoxyphenyl; and when R 1 or R 2 is a hydrogen atom, the adjacent X 1 or X 2 is not a C 1-7 alkylene; or a salt thereof exhibits a protein tyrosine phosphatase inhibitory action and is useful as a prophylactic or therapeutic agent for diabetes or the like.

  式（I）的化合物： 其中X1和X2相同或不同，每个都是主链中具有1至20个原子的键或间隔物； R1和R2中的一个是具有取代基的环基，所述取代基选自1）可选择地取代的羧基-C1-6烷氧基和2）可选择地取代的羧基-C1-6脂肪烃基，其中所述环基可选择地具有额外的取代基，另一个是可选择地取代的环基或氢原子；以及 R3、R4和R5相同或不同，每个是氢原子或取代基，或R4可以与R3或R5结合形成可选择地取代的环； 但是当R3是氢原子时，R4是氢原子且R5是甲基时，X2—R2不是4-环己基苯基；当R3是4-甲氧基苯基，R4是氢原子且R5是甲基时，X2—R2不是4-甲氧基苯基；当R1或R2是氢原子时，相邻的X1或X2不是C1-7烷基； 或其盐具有蛋白酪氨酸磷酸酶抑制作用，并且可用作糖尿病等疾病的预防或治疗剂。
• Ring-opening of tertiary cyclopropanols derived from β-diketones
  作者：Le-Zhen Li、Bin Xiao、Qing-Xiang Guo、Song Xue

  DOI：10.1016/j.tet.2006.05.064

  日期：2006.8

  The ring-opening reaction of 1,2-di substituted cyclopropanols, prepared from beta-diketones, mediated by Cu(NO3)(2), p-TsOH, and NaOH is reported. The Cu(II)-mediated ring-opening of cyclopropanols gave alpha-methylene-gamma-diketones in good yields. The reaction took place at the less substituted carbon of the cyclopropanols, involving mild conditions and a simple procedure. The reaction induced by p-TsOH in CH2O2 afforded alpha-methyl-gamma-diketones as the major product with minor amounts of 8-diketones. The 2,3,5-tri substituted furans were obtained in high yields when the ring-opening reaction was mediated by p-TsOH in methanol under reflux conditions. In the presence of sodium hydroxide the reaction proceeded smoothly in preference to the formation of beta-diketones, particularly for substrates with an aromatic group on the cyclopropane. (c) 2006 Elsevier Ltd. All rights reserved.