6-(benzyloxy)hexan-1-ol methanesulfonate | 170656-31-2

• 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: 6-(benzyloxy)hexan-1-ol methanesulfonate
• 英文别名: 6-benzyloxyhexyl methanesulfonate；BnO(CH2)6OMs；6-(Benzyloxy)hexyl methanesulfonate；6-phenylmethoxyhexyl methanesulfonate
• CAS: 170656-31-2
• 化学式: C₁₄H₂₂O₄S
• 分子量: 286.392
• InChiKey: IZXSODCTKRBSNH-UHFFFAOYSA-N

物化性质

• 沸点：
  428.4±28.0 °C(Predicted)
• 密度：
  1.122±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  6-(benzyloxy)hexan-1-ol methanesulfonate 在 甲基溴化镁 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以98%的产率得到6-(苄氧基)-1-己醇
  参考文献：
  名称：

  A Selective and Efficient Demesylation Using Methylmagnesium Bromide

  摘要：

  The chemoselective regeneration of alcohols from mesylates was accomplished by using methylmagnesium bromide in THF.

  DOI：

  10.1080/00397919508015459
• 作为产物：
  描述：

  苯甲醇 在 吡啶 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 6-(benzyloxy)hexan-1-ol methanesulfonate
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of N-Alkylated Deoxynojirimycin (DNJ) Derivatives for the Treatment of Dengue Virus Infection

  摘要：

  We recently described the discovery of oxygenated N-alkyl deoxynojirimycin (DNJ) derivative 7 (CM-10-18) with antiviral activity against dengue virus (DENY) infection both in vitro and in vivo. This imino sugar was promising but had an EC50 against DENY in BHK cells of 6.5 mu M, which limited its use in in vivo. Compound 7 presented structural opportunities for activity relationship analysis, which we exploited and report here. These structure activity relationship studies led to analogues 2h, 2l, 3j, 3l, 3v, and 4b-4c with nanomolar antiviral activity (EC50 = 0.3-0.5 mu M) against DENY infection, while maintaining low cytotoxicity (CC50 > 500 mu M, SI > 1000). In male Sprague-Dawley rats, compound 3l was well tolerated at a dose up to 200 mg/kg and displayed desirable PK profiles, with significantly improved bioavailability (F = 92 +/- 4%).

  DOI：

  10.1021/jm300171v

文献信息

• Synthesis of Extremely Simplified Compounds Possessing the Key Pharmacophore Units of Taxol, Phenylisoserine and Oxetane Moieties.
  作者：Kaoru FUJI、Yukari WATANABE、Tadamune OHTSUBO、Mohammad NURUZZAMAN、Yoshio HAMAJIMA、Michiaki KOHNO

  DOI：10.1248/cpb.47.1334

  日期：——

  Straight chain compounds having a phenylisoserine unit and an oxetane ring at the α- and ω-position, respectively as extremely simplified analogues of taxol were prepared. None of these compounds showed promising tubulin inhibitory activity.

  合成了直链化合物，这些化合物在α-和ω-位分别具有苯基异氨酸单元和氧杂环，作为紫杉醇的极简化类似物。然而，这些化合物均未表现出良好的微管抑制活性。
• Ionic and Organometallic Reductions with N-Heterocyclic Carbene Boranes
  作者：Qianli Chu、Malika Makhlouf Brahmi、Andrey Solovyev、Shau-Hua Ueng、Dennis P. Curran、Max Malacria、Louis Fensterbank、Emmanuel Lacôte

  DOI：10.1002/chem.200902450

  日期：2009.12.7

  Surgical reduction: N‐Heterocyclic carbene–borane complexes such as depicted are neutral, organic soluble analogues of borohydride anions with a weak hydridic character, compatible with organometallic catalysis. They are applicable for surgical reductions in complex, multifunctional molecules.

  外科手术还原：如图所示，N-杂环卡宾-硼烷络合物是硼氢化物阴离子的中性有机可溶类似物，具有较弱的氢化特性，可与有机金属催化相容。它们适用于通过手术减少复杂的多功能分子。
• Self-assembling behaviour of chiral calamitic monoacrylates targeted for polymer stabilisation of polar smectic phases in chiral liquid crystals
  作者：Ewelina Dmochowska、Jakub Herman、Michał Czerwiński、Sergei Stulov、Alexej Bubnov、Przemysław Kula

  DOI：10.1016/j.molliq.2021.115723

  日期：2021.6

  with the components of modern ferroelectric and antiferroelectric liquid crystalline mixtures, are confirmed by mass spectrometry (electron ionization) analysis and proton/carbon nuclear magnetic resonance. All the reactive mesogens possess the self-assembling, i.e. liquid crystalline behaviour with high tendency to create smectic phases in a broad temperature range, which was confirmed by a polarizing

  斜向和反斜向手性液晶相的稳定和控制仍然是一项实际而突出的任务。这项工作介绍了基于手性联苯胺酸酯和苯基联苯-4-羧酸酯核心的反应性末端基团远离手性链的新型手性卡拉曼反应性介晶单丙烯酸酯的设计和介晶性质。该化合物的结构与现代铁电和反铁电液晶混合物的成分兼容，已通过质谱分析（电子电离）分析和质子/碳核磁共振得到了证实。所有的反应性液晶元都具有自组装性，即液晶行为，在宽温度范围内很容易形成近晶相，这已经通过偏光光学显微镜得到了证实，差示扫描量热法和宽带介电谱。通过设计的单丙烯酸酯对具有手性近晶相的高级多组分混合物进行进一步的交联步骤进行掺杂，可以成为稳定各种状态下铁电相和反铁电相的有效且功能强大的工具，因此可以对称地确定开关时间。模式采用表面稳定的几何形状；对于光电子学来说，这是一项非常突出的任务。而且，特定反应性液晶元的热聚合的明显的显着趋势可以减少聚合物稳定化的缺点。通过设计的单丙烯酸酯对具有
• [EN] DEGRADERS OF GRK2 AND USES THEREOF<br/>[FR] AGENTS DE DÉGRADATION DE GRK2 ET LEURS UTILISATIONS
  申请人：CYGNAL THERAPEUTICS INC

  公开号：WO2022159688A1

  公开（公告）日：2022-07-28

  Provided herein are compounds (e.g., compounds of Formulae (A-I), (B-I), (C-I)), and pharmaceutically acceptable salts, stereoisomers, tautomers, isotopically labeled derivatives, solvates, hydrates, polymorphs, co-crystals, and prodrugs thereof, pharmaceutical compositions thereof, and kits comprising the same. The compounds provided herein are degraders of GRK2 proteins and are therefore useful for,e.g., treating and/or preventing diseases (e.g., cancer) in a subject, for inhibiting tumor growth in a subject, for inhibiting the activity of GRK2 and/or degrading a GRK2 protein in vitro or in vivo, etc. In certain embodiments, the compounds provided herein are selective for GRK2. Also provided herein are methods and synthetic intermediates useful in the preparation of compounds described herein.

  本文提供了化合物（例如，式（A-I）、（B-I）、（C-I）的化合物），以及其药学上可接受的盐、立体异构体、互变异构体、同位素标记衍生物、溶剂化物、水合物、多晶体、共晶体和其前药，以及其制备的药物组合物和包含它们的试剂盒。本文提供的化合物是GRK2蛋白降解剂，因此可用于治疗和/或预防受试者的疾病（例如，癌症），抑制受试者的肿瘤生长，抑制在体内或体外GRK2的活性和/或降解GRK2蛋白等。在某些实施例中，本文提供的化合物对GRK2具有选择性。本文还提供了制备所述化合物的方法和合成中间体。
• Synthesis and Properties of New Lipophilic Macrotricyclic Cylindrical Cryptands
  作者：Silvio Quici、Amedea Manfredi、Laura Raimondi、Angelo Sironi

  DOI：10.1021/jo00125a025

  日期：1995.10

  Cylindrical cryptands 2a-c, in which two 1,7-dioxa-4,10-diazacyclododecane rings are connected by two equally substituted propylene bridges, have been obtained in appreciable yields by a ''one-pot'' synthesis. The assembling of the macrotricyclic structure is likely driven by the template effect of metal cations. These compounds, both as free receptors or as complexes, exist as cis and trans diastereoisomers, which do not interconvert and have been separated and characterized by X-ray analysis. The extraction constants (K-e) of cryptands 2 for alkali picrates under CHCl3/H2O and solid/liquid two-phase conditions have been measured by UV-vis spectrophotometry. The complexation behavior of cryptands 2 has been rationalized analyzing the preorganization of binding sites in the minimum energy conformations obtained by molecular mechanics calculations. Minimum energy conformations have been calculated also for the previously reported cryptands 1 and have been compared with those of 2. Results fit reasonably well with those of X-ray structures.