4-hydroxybenzylglycol ether

• 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-hydroxybenzylglycol ether
• 英文别名: 4-((2-hydroxyethoxy)methyl)phenol；4-[(2-Hydroxyethoxy)methyl]phenol；4-(2-hydroxyethoxymethyl)phenol
• 化学式: C₉H₁₂O₃
• 分子量: 168.192
• InChiKey: NZKSMKXYYTXWMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-hydroxybenzylglycol ether 、 3-bromo-6-(tetrahydro-2H-pyran-2-yl)-6H-thieno[2,3-e]-indazole-1,1-dioxide 在 caesium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以81%的产率得到3-(4-((2-hydroxyethoxy)methyl)phenoxy)-6-(tetrahydro-2H-pyran-2-yl)-6H-thieno[2,3-e]indazole-1,1-dioxide
  参考文献：
  名称：

  噻吩并[2,3-e]吲唑衍生物作为新型口服选择性雌激素受体降解剂的发现，具有高度改善的抗肿瘤作用和良好的成药性

  摘要：

  内分泌治疗在早期和转移性雌激素受体 α 阳性 (ERα+) 乳腺癌 (BC) 的治疗中受到新发耐药和获得性耐药的极大限制。由于独特的机制，选择性雌激素受体降解剂 (SERD) （如氟维司群）为内分泌治疗组合提供了新策略。在此，我们通过用 6 H-噻吩并[2,3 - e ]吲唑代替 6-羟基苯并噻吩，公开了基于结构的 LSZ102 优化。随后的丙烯酸 degron 修饰使我们将化合物40确定为首选候选者。一般来说，化合物40显示出比先导 LSZ102 更好的药理学特征，表现出对野生型或他莫昔芬抗性 MCF-7 细胞的生长抑制，有效的 ERα 降解，以及优越的药代动力学特性，包括大脑在内的定向靶组织分布，以及强大的抗肿瘤功效小鼠乳腺癌异种移植模型。目前，40 个正在临床前试验中进行评估。

  DOI：

  10.1021/acs.jmedchem.2c00008
• 作为产物：
  描述：

  对甲酚 在 水 、 氧气 、 乙二醇 、 sodium hydroxide 作用下， 反应 18.0h， 生成 对羟基苯甲醇 、 4-hydroxybenzylglycol ether 、 对羟基苯甲醛
  参考文献：
  名称：

  Practical Process for the Air Oxidation of Cresols:  Part B. Evaluation of the Laboratory-Scale Oxidation Process

  摘要：

  Mechanistic proposals and predictions made in a preceding paper (Part A) were evaluated by carrying out the catalytic air oxidation of p-cresol in an alternative solvent system, comprising either a mixture of ethylene glycol and acetic acid (for oxidations under acidic conditions) or ethylene glycol and water (for oxidations under basic conditions). The results obtained in these experiments confirmed that ethylene glycol acts as a nucleophile in these solvent systems, thereby stabilizing the quinomethide intermediate and resulting in highly efficient oxidations in both alkaline and acidic media. 4-Hydroxybenzaldehyde, the desired product, was thus obtained in isolated yields of up to 98% and purities >99%. The inherent drawbacks associated with alkaline methanol and aqueous acetic acid solutions were thus circumvented, and the result is a highly efficient process for the production of 4-hydroxybenzaidehyde.

  DOI：

  10.1021/op049844j

文献信息

• COMPOUND, RESIST COMPOSITION CONTAINING COMPOUND AND PATTERN FORMATION METHOD USING SAME
  申请人：The School Corporation Kansai University

  公开号：US20200057370A1

  公开（公告）日：2020-02-20

  A resist composition comprising one or more tannin compounds selected from the group consisting of a tannin comprising at least one crosslinking reactive group in the structure and a derivative thereof, and a resin obtained using the tannin or the derivative as a monomer.
• [EN] PROCESS FOR THE PRODUCTION OF HYDROXY-SUBSTITUTED AROMATIC ALDEHYDES AND KETONES<br/>[FR] PROCEDE DE PRODUCTION DE CETONES ET D'ALDEHYDES AROMATIQUES SUBSTITUES PAR HYDROXY
  申请人：DOW AGROSCIENCES LLC

  公开号：WO2001009072A1

  公开（公告）日：2001-02-08

  A method of oxidising an alkylphenol of the formula (I) or (II) to a corresponding hydroxybenzaldehyde or hydroxyacetophenone, wherein: X is CH3 or CH2CH3; each of R1 to R4 is H, Cl, Br, C1-C10 alkyl, or C1-C10 alkoxy; R1 and R2 and R3 or R3 and R4 together may be -(CH2)n-; wherein n is 3 to 6, provided only one of R1 and R2, R2 and R3 or R3 and R4 is -(CH2)n-; includes the steps of producing a reaction medium of the alkylphenol in a solvent which comprises a dihydric alcohol and is acidic or alkaline and reacting the alkylphenol with oxygen in the presence of an oxidation catalyst. Examples of suitable dihydric alcohols are ethylene glycol, 1,2-propanediol, 1,3-propanediol and 1,4-butanediol.
• Practical Process for the Air Oxidation of Cresols:  Part B. Evaluation of the Laboratory-Scale Oxidation Process
  作者：Benita Barton、Catherine G. Logie、Barbara M. Schoonees、Bernard Zeelie

  DOI：10.1021/op049844j

  日期：2005.1.1

  Mechanistic proposals and predictions made in a preceding paper (Part A) were evaluated by carrying out the catalytic air oxidation of p-cresol in an alternative solvent system, comprising either a mixture of ethylene glycol and acetic acid (for oxidations under acidic conditions) or ethylene glycol and water (for oxidations under basic conditions). The results obtained in these experiments confirmed that ethylene glycol acts as a nucleophile in these solvent systems, thereby stabilizing the quinomethide intermediate and resulting in highly efficient oxidations in both alkaline and acidic media. 4-Hydroxybenzaldehyde, the desired product, was thus obtained in isolated yields of up to 98% and purities >99%. The inherent drawbacks associated with alkaline methanol and aqueous acetic acid solutions were thus circumvented, and the result is a highly efficient process for the production of 4-hydroxybenzaidehyde.
• Discovery of Thieno[2,3-<i>e</i>]indazole Derivatives as Novel Oral Selective Estrogen Receptor Degraders with Highly Improved Antitumor Effect and Favorable Druggability
  作者：Zhengyu Lu、Yangzhi Cao、Dan Zhang、Xin Meng、Bin Guo、Deyu Kong、Yushe Yang

  DOI：10.1021/acs.jmedchem.2c00008

  日期：2022.4.14

  Endocrine therapies in the treatment of early and metastatic estrogen receptor α positive (ERα+) breast cancer (BC) are greatly limited by de novo and acquired resistance. Selective estrogen receptor degraders (SERDs) like fulvestrant provide new strategies for endocrine therapy combinations due to unique mechanisms. Herein, we disclose our structure-based optimization of LSZ102 by replacing 6-hydroxybenzothiophene

  内分泌治疗在早期和转移性雌激素受体 α 阳性 (ERα+) 乳腺癌 (BC) 的治疗中受到新发耐药和获得性耐药的极大限制。由于独特的机制，选择性雌激素受体降解剂 (SERD) （如氟维司群）为内分泌治疗组合提供了新策略。在此，我们通过用 6 H-噻吩并[2,3 - e ]吲唑代替 6-羟基苯并噻吩，公开了基于结构的 LSZ102 优化。随后的丙烯酸 degron 修饰使我们将化合物40确定为首选候选者。一般来说，化合物40显示出比先导 LSZ102 更好的药理学特征，表现出对野生型或他莫昔芬抗性 MCF-7 细胞的生长抑制，有效的 ERα 降解，以及优越的药代动力学特性，包括大脑在内的定向靶组织分布，以及强大的抗肿瘤功效小鼠乳腺癌异种移植模型。目前，40 个正在临床前试验中进行评估。