4-(allyloxy)phenyl-4-methylbenzenesulfonate | 157259-26-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(allyloxy)phenyl-4-methylbenzenesulfonate
• 英文别名: (4-Prop-2-enoxyphenyl) 4-methylbenzenesulfonate
• CAS: 157259-26-2
• 化学式: C₁₆H₁₆O₄S
• 分子量: 304.367
• InChiKey: INGAGVULUCQXAM-UHFFFAOYSA-N

物化性质

• 熔点：
  47-48 °C(Solv: acetic acid (64-19-7); ligroine (8032-32-4))
• 沸点：
  455.5±45.0 °C(Predicted)
• 密度：
  1.210±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(allyloxy)phenyl-4-methylbenzenesulfonate 在 氢氧化钾 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-[4-(allyloxy)phenoxy]benzaldehyde
  参考文献：
  名称：

  Antidiabetic Activity of Passive Nonsteroidal Glucocorticoid Receptor Modulators

  摘要：

  Much has been learned about the consequences of glucocorticoid receptor antagonism by studying steroidal active antagonists such as RU-38486 (1). In the liver glucocorticoid receptor antagonism suppresses hepatic glucose production decreasing plasma glucose levels; however, extrahepatic antagonism produces several undesirable side effects including activation of the hypothalamic pituitary adrenal axis. A series of nonsteroidal passive N-(3-dibenzylamino-2-alkyl-phenyl)-methanesulfonamide glucocorticoid receptor modulators was discovered. Liver selective and systemically available members of this series were found and characterized in diabetes and side effect rodent models. A highly liver selective member of this series, acid 14, shows efficacy in the ob/ob model of diabetes. It lowers plasma glucose, cholesterol, and free fatty acid concentrations and reduces the rate of body weight gain. The structurally related systemically available passive modulator 12 lowers glucose, HbA(1c), triglyceride, free fatty acid, and cholesterol levels. Interestingly, it did not acutely activate the hypothalamic pituitary adrenal axis in unstressed CD-1 mice or have the abortive effects observed with 1. These results indicate that passive GR antagonists may have utility as antidiabetic agents.

  DOI：

  10.1021/jm050205o
• 作为产物：
  描述：

  4-丙烯氧基苯酚 、 对甲苯磺酰氯 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 10.0h， 以99.2%的产率得到4-(allyloxy)phenyl-4-methylbenzenesulfonate
  参考文献：
  名称：

  Novel polymeric nonionic photoacid generators and corresponding polymer Langmuir–Blodgett (LB) films for photopatterning

  摘要：

  A series of new polymeric nonionic photoacid generators (PACs) and PAG-bound polymers designed for photoresist materials in Langmuir-Blodgett (LB) films have been synthesized and characterized. The novel polymer could form a stable and condensed monolayer on water surface, which could be transferred successfully onto solid substrate. Upon deep UV irradiation, the acid generated by the photoacid generator catalyzed the naphthyl moiety to liberate naphthol and regenerate carboxyl in the exposed region. The rent moiety could dissolve in alkaline aqueous, resulting in a fine positive tone resist patterns with a resolution of 0.75 mu m. Sensitivity curves and TGA studies revealed that the high sensitivity in 248 nm irradiation was attributed to the present of PAG units incorporated in the polymer chains. The result of translated gold pattern with the same resolution as the resist pattern also demonstrated that the resist LB films had sufficient resistance to wet etching process. (C) 2011 Published by Elsevier B.V.

  DOI：

  10.1016/j.jphotochem.2011.01.015

文献信息

• Development of a Catalytic Electron Transfer System Mediated by Transition Metal Ate Complexes:  Applicability and Tunability of Electron-Releasing Potential for Organic Transformations
  作者：Masanobu Uchiyama、Yotaro Matsumoto、Shinji Nakamura、Tomohiko Ohwada、Nagao Kobayashi、Natsuno Yamashita、Atsushi Matsumiya、Takao Sakamoto

  DOI：10.1021/ja039674a

  日期：2004.7.1

  We have developed a catalytic electron transfer (ET) system composed of a transition metal ate complex (Me3M(II)Li; M = Co(II), Mn(II), Fe(II)) and magnesium. This system (catalytic Me3M(II)Li/Mg) turned out to be effective for various ET reactions, such as the desulfonylation of N-phenylsulfonyl amides, and others (the chemoselective cleavage of O-allyl groups, the reduction of nitro groups, the partial

  我们开发了一种催化电子转移 (ET) 系统，由过渡金属盐络合物 (Me3M(II)Li；M = Co(II)、Mn(II)、Fe(II)) 和镁组成。该系统（催化 Me3M(II)Li/Mg）被证明对各种 ET 反应有效，例如 N-苯基磺酰胺的脱磺酰化，以及其他（O-烯丙基的化学选择性裂解、硝基的还原、二酮的部分还原，以及二苯基碘盐的还原偶联）。该系统的 ET 能力可以通过改变 ate 配合物的配体来调整。实验和电化学证明了这种可调性：烷氧基连接和双阴离子型 ET 复合物分别显示减弱和增强的还原能力。ET 能力的改变通过电化学测量和化学反应进行评估。这些结果为设计各种定制的 ET 复合物提供了基础。
• Ether Aryl Sulfonic Acid Esters with Improved Antimalarial/Anticancer Activities
  作者：Lynn M. Betts、Nga Chiu Tam、S. M. Humayun Kabir、Richard F. Langler、Ian Crandall

  DOI：10.1071/ch04299

  日期：——

  previous report showed that our current benchmark agent, 4-methoxyphenyl p-toluenesulfonate, is a selective antimalarial/anticancer agent. A series of related sulfones and sulfonic acid esters is now examined. 4-Allyloxyphenyl p-toluenesulfonate is a superior antimalarial/anticancer agent. 4-Methoxyphenyl 4-nitrobenzenesulfonate is a superior antimalarial agent, but shows poorer inhibition of human skin

  我们之前的报告显示，我们目前的基准药物对甲苯磺酸 4-甲氧基苯酯是一种选择性抗疟/抗癌剂。现在研究了一系列相关的砜和磺酸酯。4-烯丙氧基苯基对甲苯磺酸盐是一种优越的抗疟疾/抗癌剂。4-Methoxyphenyl 4-nitrobenzosulfonate 是一种优良的抗疟药，但对人体皮肤癌细胞的抑制作用较差。
• An Efficient Method for the Deallylation of Allyl Aryl Ethers Using Electrochemically Generated Nickel
  作者：Akito Yasuhara、Atsushi Kasano、Takao Sakamoto

  DOI：10.1021/jo9824706

  日期：1999.5.1
• Antidiabetic Activity of Passive Nonsteroidal Glucocorticoid Receptor Modulators
  作者：J. T. Link、Bryan Sorensen、Jyoti Patel、Marlena Grynfarb、Annika Goos-Nilsson、Jiahong Wang、Steven Fung、Denise Wilcox、Brad Zinker、Phong Nguyen、Bach Hickman、James M. Schmidt、Sue Swanson、Zhenping Tian、Thomas J. Reisch、Gary Rotert、Jia Du、Benjamin Lane、Thomas W. von Geldern、Peer B. Jacobson

  DOI：10.1021/jm050205o

  日期：2005.8.1

  Much has been learned about the consequences of glucocorticoid receptor antagonism by studying steroidal active antagonists such as RU-38486 (1). In the liver glucocorticoid receptor antagonism suppresses hepatic glucose production decreasing plasma glucose levels; however, extrahepatic antagonism produces several undesirable side effects including activation of the hypothalamic pituitary adrenal axis. A series of nonsteroidal passive N-(3-dibenzylamino-2-alkyl-phenyl)-methanesulfonamide glucocorticoid receptor modulators was discovered. Liver selective and systemically available members of this series were found and characterized in diabetes and side effect rodent models. A highly liver selective member of this series, acid 14, shows efficacy in the ob/ob model of diabetes. It lowers plasma glucose, cholesterol, and free fatty acid concentrations and reduces the rate of body weight gain. The structurally related systemically available passive modulator 12 lowers glucose, HbA(1c), triglyceride, free fatty acid, and cholesterol levels. Interestingly, it did not acutely activate the hypothalamic pituitary adrenal axis in unstressed CD-1 mice or have the abortive effects observed with 1. These results indicate that passive GR antagonists may have utility as antidiabetic agents.
• Novel polymeric nonionic photoacid generators and corresponding polymer Langmuir–Blodgett (LB) films for photopatterning
  作者：Wenjian Xu、Tiesheng Li、Gaojian Li、Yangjie Wu、Tokuji Miyashita

  DOI：10.1016/j.jphotochem.2011.01.015

  日期：2011.3

  A series of new polymeric nonionic photoacid generators (PACs) and PAG-bound polymers designed for photoresist materials in Langmuir-Blodgett (LB) films have been synthesized and characterized. The novel polymer could form a stable and condensed monolayer on water surface, which could be transferred successfully onto solid substrate. Upon deep UV irradiation, the acid generated by the photoacid generator catalyzed the naphthyl moiety to liberate naphthol and regenerate carboxyl in the exposed region. The rent moiety could dissolve in alkaline aqueous, resulting in a fine positive tone resist patterns with a resolution of 0.75 mu m. Sensitivity curves and TGA studies revealed that the high sensitivity in 248 nm irradiation was attributed to the present of PAG units incorporated in the polymer chains. The result of translated gold pattern with the same resolution as the resist pattern also demonstrated that the resist LB films had sufficient resistance to wet etching process. (C) 2011 Published by Elsevier B.V.