estrone-3-O-ylacetic acid | 1428-66-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: estrone-3-O-ylacetic acid
• 英文别名: 3-O-caroxymethylestrone；estrone-3-oxyacetic acid；2-(((8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl)oxy)acetic acid；3-O-carboxymethylestrone；2-[[(8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-yl]oxy]acetate；(17-oxo-estra-1,3,5(10)-trien-3-yloxy)-acetic acid；O-acetic acid-estrone；ZINC04428843；NCI-86467；(17-Oxo-oestra-1,3,5(10)-trien-3-yloxy)-essigsaeure；estra-1,3,5(10)-trien-17-one-3-oxyacetic acid；3-O-(Carboxymethyl)estrone；2-[[(8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-yl]oxy]acetic acid
• CAS: 1428-66-6
• 化学式: C₂₀H₂₄O₄
• 分子量: 328.408
• InChiKey: XSDCLHQDGODZPZ-WWNBULGVSA-N

物化性质

• 熔点：
  209 °C
• 沸点：
  516.1±50.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  estrone-3-O-ylacetic acid 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以90%的产率得到beta-雌二醇 3-羧甲基醚
  参考文献：
  名称：

  Oxidation of organic molecules in homogeneous aqueous solution catalyzed by hybrid biocatalysts (based on the Trojan Horse strategy)

  摘要：

  New anionic metalloporphyrin-estradiol conjugates have been synthesized and fully characterized, and have been further associated to a monoclonal anti-estradiol antibody 7A3, to generate new artificial metalloenzymes following the so-called 'Trojan Horse' strategy. The spectroscopic characteristics and dissociation constants of these complexes were similar to those obtained for the artificial metalloproteins obtained by association of cationic metalloporphyrin-estradiol conjugates to 7A3. This demonstrates that the nature of the porphyrin substituents, anionic or cationic, had little influence on the association with the antibody that is mainly driven by the tight association of the estradiol anchor with the binding pocket of the antibody.These new biocatalysts appeared to have an interesting catalytic activity in oxidation reactions. The iron(III)-anionic-porphyrin-estradiol-antibody complexes were found able to catalyze the chemoselective and slightly enantioselective (ee = 10%) sulfoxidation of sulfides by H2O2. The Mn(III)-porphyrin-estradiol-antibody complexes were found to catalyze the oxidation of styrene by KHSO5, the Mn(III)-cationic-porphyrin-estradiol-antibody complexes even showing the highest yields so far reported for the oxidation of styrene catalyzed by artificial metalloproteins. However, a lack of chemoselectivity and enantioselectivity was observed, which was probably due to a weak interaction of the metalloporphyrin cofactor with the binding pocket of antibody 7A3, as suggested by the similar UV-visible characteristics and catalytic activities obtained with both anionic and cationic porphyrins. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.03.050
• 作为产物：
  描述：

  雌酚酮 在 sodium hydride 作用下， 以 水 为溶剂， 反应 0.75h， 生成 estrone-3-O-ylacetic acid
  参考文献：
  名称：

  （三氟甲基硒烯基）甲基硫属酰基作为新兴的氟化基团：在光氧化还原催化下的合成和亲脂性的测定

  摘要：

  通过基于无金属的光氧化还原催化的脱羧三氟甲基硒化反应的高效两步策略描述了带有（三氟甲基硒烯基）甲基硫属碳酰基的分子的合成，收率高达88％，在流化学条件下提高到98％。流动方法还可以扩大反应规模。研究了该关键反应的机理。这些新兴群体的理化特性是通过确定其Hansch-Leo亲脂性参数（高达2.24的高值）来进行的。该反应还扩展至全氟烷基硒代化，产率高达95％。最后，该方法已成功应用于相关生物活性分子（如生育酚或雌酮衍生物）的功能化。

  DOI：

  10.1002/chem.202100053

文献信息

• Camptothecin derivatives
  申请人：California Pacific Medical Center

  公开号：US06350756B1

  公开（公告）日：2002-02-26

  (20S) esters of camptothecin analogs are provided. The compounds are (20S) esters of an oxyalkanoic acid and camptothecin, which is optionally substituted at the 7, 9, 10, 11, and 12 positions of the camptothecin ring. The compounds are useful for treating cancer.

  紫杉醇类似物的(20S)酯类化合物已提供。这些化合物是紫杉醇和氧烷羧酸的(20S)酯类，紫杉醇在7、9、10、11和12位的环上可选择性地被取代。这些化合物可用于治疗癌症。
• Radical Decarboxylative Fluorination of Aryloxyacetic Acids Using<i>N</i>-Fluorobenzenesulfonimide and a Photosensitizer
  作者：Joe C. T. Leung、Glenn M. Sammis

  DOI：10.1002/ejoc.201500038

  日期：2015.4

  carboxylic acids was developed that uses photosensitizers and N-fluorobenzenesulfonimide (NFSI). Utilization of the oxidatively mild fluorine transfer agent NFSI enabled the synthesis of fluoromethyl ethers that were previously inaccessible with decarboxylative fluorinations performed with Selectfluor. Mechanistic studies are consistent with the photosensitizer effecting oxidation of the aryloxyacetic acid

  氟化甲氧基芳烃正在成为农用化学品和药物中的重要基序。开发了一种通过羧酸的直接氟脱羧合成单氟甲氧基芳烃的新技术，该技术使用光敏剂和 N-氟苯磺酰亚胺 (NFSI)。利用氧化性温和的氟转移剂 NFSI 能够合成氟甲基醚，而以前使用 Selectfluor 进行脱羧氟化是无法获得这些氟甲基醚的。机理研究与影响芳氧基乙酸氧化的光敏剂一致。
• 3-SUBSTITUTED ESTRA-1,3,5(10),16-TETRAENE DERIVATIVES, METHODS FOR THE PRODUCTION THEREOF, PHARMACEUTICAL PREPARATIONS CONTAINING SAME, AND USE THEREOF FOR THE PRODUCTION OF MEDICAMENTS
  申请人：BAYER PHARMA AKTIENGESELLSCHAFT

  公开号：US20150210734A1

  公开（公告）日：2015-07-30

  The invention relates to AKR1C3 inhibitors and to processes for their preparation, to their use for the treatment and/or prophylaxis of diseases and also to their use for preparing medicaments for the treatment and/or prophylaxis of diseases, in particular bleeding disorders and endometriosis.

  这项发明涉及AKR1C3抑制剂及其制备方法，以及它们用于治疗和/或预防疾病的用途，还包括它们用于制备用于治疗和/或预防疾病的药物的用途，特别是用于出血障碍和子宫内膜异位症的治疗。
• Homo-camptothecin derivatives
  申请人：——

  公开号：US20040034050A1

  公开（公告）日：2004-02-19

  C-20 esters of homo-camptothecin analogues are provided. The compounds are C-20 esters of an oxyalkanoic acid and homo-camptothecin, which are optionally substituted at the 7, 9, 10, 11, and 12 positions of the homo-camptothecin ring. The compounds are useful for treating cancer.

  本发明提供了同卡培他辛类化合物的C-20酯。这些化合物是氧基烷酸和同卡培他辛的C-20酯，可选择地在同卡培他辛环的7、9、10、11和12位置进行取代。这些化合物可用于治疗癌症。
• Two-in-one metallaphotoredox cross-couplings enabled by a photoactive ligand
  作者：Jianbin Li、Chia-Yu Huang、Chao-Jun Li

  DOI：10.1016/j.chempr.2022.05.011

  日期：2022.9

  ability to streamline organic synthesis, cross-couplings have become fundamental reactions in many settings. In photoinduced cross-coupling chemistry, metallaphotoredox catalysis remains state-of-the-art, typically featuring a dual catalytic partnership of a chromophoric compound and an organometallic complex. However, designing such a highly variable, multicomponent linchpin ranks among the most challenging

  交叉偶联因其简化有机合成的能力而备受赞誉，已成为许多环境中的基本反应。在光诱导交叉偶联化学中，金属光氧化还原催化仍然是最先进的，通常具有发色化合物和有机金属配合物的双重催化伙伴关系。然而，设计这种高度可变的多组分关键销是合成实践中最具挑战性的工作之一，因为确定最佳组合通常需要大量的实验。在这里，我们通过设计一种可以与一系列过渡金属络合并用作“二合一”金属光氧化还原催化剂的光活性配体，概述了该问题的简单而通用的解决方案。我们的双功能系统与多种亲核和亲电偶联伙伴池兼容，并且在可见光驱动的 C-C 和 C-X 键形成中具有很高的能力。我们设想这种非经典工具包将为新的耦合反应打开化学空间，并激发广泛科学界的未来研究工作。