(1R^*,2R^*)-3-<(phenylmethyl)oxy>cyclohexanol

• 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: (1R^*,2R^*)-3-<(phenylmethyl)oxy>cyclohexanol
• 英文别名: (1S^*,3R^*)-3-<(phenylmethyl)oxy>cyclohexanol；3-benzyloxycyclohexan-1-ol；3-(benzyloxy)cyclohexanol；3-phenylmethoxycyclohexan-1-ol
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: RFCYVWGCOXVSBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R^*,2R^*)-3-<(phenylmethyl)oxy>cyclohexanol 在 水 、 正庚烷 、 水合甲醇 作用下， 以 甲醇 为溶剂， 以3.6 g of the desired (1S,3R)-3-benzyloxycyclohexan-1-ol were obtained的产率得到cis-3-(benzyloxy)cyclohexanol
  参考文献：
  名称：

  Process for preparing the enantiomeric forms of cis-configured 1,3-cyclohexanediol derivatives

  摘要：

  本发明描述了一种通过酶促光学分离制备手性、非外消旋的顺式构型1,3-二取代环己烷醇衍生物的方法，式（I）中基团的定义如上。

  公开号：

  US20040209931A1
• 作为产物：
  描述：

  cis-3-(benzyloxy)cyclohexanol 以 乙酸乙烯酯 、 二氯甲烷 为溶剂， 反应 26.0h， 生成 (1R^*,2R^*)-3-<(phenylmethyl)oxy>cyclohexanol
  参考文献：
  名称：

  Process for preparing the enantiomeric forms of cis-configured 1,3-cyclohexanediol derivatives

  摘要：

  本发明描述了一种通过酶促光学分离制备手性、非外消旋的顺式构型1,3-二取代环己烷醇衍生物的方法，式（I）中基团的定义如上。

  公开号：

  US20040209931A1

文献信息

• CYCLOHEXANE ANALOGUES AS GPR119 AGONISTS
  申请人：Kang Sang Uk

  公开号：US20120053180A1

  公开（公告）日：2012-03-01

  This invention relates to a series of substituted cyclohexane containing analogues which are agonists of GPR119 intended to treat metabolic diseases mediated by GPR119 including Type I & II diabetes mellitus. Diabetes mellitus is an ever-increasing threat to human health causing various complications (blindness, kidney failure, neuropathy, heart attack, stroke, etc.). Recently it was found that activation of GPR119 which is highly expressed in pancreatic beta cells causes glucose dependent insulin secretion and GLP-1 release. Many pharmaceuticals are currently developing GPR119 agonists and herein we disclose alternative GPR119 agonists. Our invention describes GPR119 agonists having structural Formula (I), pharmaceutically acceptable salt or solvate of Formula (I), isomer or prodrug of Formula (I), and combination therapy of Formula (I) with other anti-diabetic drugs like DPP-IV inhibitors and/or insulin sensitizers.

  这项发明涉及一系列含有替代基的环己烷类似物，这些类似物是 GPR119 激动剂，旨在治疗由 GPR119 介导的代谢性疾病，包括I型和II型糖尿病。糖尿病是对人类健康构成日益增加的威胁，导致各种并发症（失明、肾衰竭、神经病变、心脏病发作、中风等）。最近发现，激活在胰岛素β细胞中高表达的 GPR119 会导致葡萄糖依赖性胰岛素分泌和 GLP-1 释放。许多制药公司目前正在开发 GPR119 激动剂，我们在此披露了替代的 GPR119 激动剂。我们的发明描述了具有结构式（I）的 GPR119 激动剂，结构式（I）的药学上可接受的盐或溶剂，结构式（I）的异构体或前药，以及结构式（I）与其他抗糖尿病药物（如 DPP-IV 抑制剂和/或胰岛素增敏剂）的联合治疗。
• Origin of High Diastereoselectivity in Reactions of Seven‐Membered‐Ring Enolates
  作者：Olga Lavinda、Collin H. Witt、K. A. Woerpel

  DOI：10.1002/anie.202114183

  日期：2022.3.28

  The diastereoselective reactions of chiral seven-membered-ring enolates have been systematically investigated. Diastereoselectivity was found to be general for ϵ-lactams, ϵ-lactones, and cycloheptanones with various substituent patterns. Computational investigations provided insight into the origin of the diastereoselectivity. A model for predicting the stereochemistry of seven-membered-ring enolate

  手性七元环烯醇化物的非对映选择性反应已被系统研究。发现对于具有各种取代基模式的ε-内酰胺、ε-内酯和环庚酮来说，非对映选择性是普遍的。计算研究提供了对非对映选择性起源的深入了解。提出了预测七元环烯醇化物烷基化立体化学的模型。
• Development of Noviomimetics as C-Terminal Hsp90 Inhibitors
  作者：Mercy Anyika、Mason McMullen、Leah K. Forsberg、Rick T. Dobrowsky、Brian S. J. Blagg

  DOI：10.1021/acsmedchemlett.5b00331

  日期：2016.1.14

  KU-32 and KU-596 are novobiocin-derived, C terminal heat shock protein 90 (Hsp90) modulators that induce Hsp70 levels and manifest neuroprotective activity. However, the synthetically complex noviose sugar requires 10 steps to prepare, which makes translational development difficult. In this study, we developed a series of "noviomimetic" analogues of KU-596, which contain noviose surrogates that can be easily prepared, while maintaining the ability to induce Hsp70 levels. Both sugar and sugar analogues were designed, synthesized, and evaluated in a luciferase reporter assay, which identified compound 37, a benzyl containing noviomimetic, as the most potent inducer of Hsp70.
• Targeting Mobilization of Ferrous Iron in <i>Pseudomonas aeruginosa</i> Infection with an Iron(II)-Caged LpxC Inhibitor
  作者：Brian R. Blank、Poulami Talukder、Ryan K. Muir、Erin R. Green、Eric P. Skaar、Adam R. Renslo

  DOI：10.1021/acsinfecdis.9b00057

  日期：2019.8.9

  Iron is essential to all life, and competition for this vital nutrient is central to host-pathogen interactions during infection. The opportunistic Gram-negative pathogen Pseudomonas aeruginosa utilizes a diverse array of iron-acquisition strategies, including those enabling import of extracellular ferrous iron. We hypothesize that soluble and redox-active ferrous iron can be employed to activate caged antibiotics at sites of infection in vivo. Here we describe new chemistry that expands the application of our laboratory's Fe2+-activated-prodrug chemistry to cage hydroxamic acids, a class of drugs that present manifold development challenges. We synthesize the caged form of a known LpxC inhibitor and show that it is efficacious in an acute P. aeruginosa mouse-lung infection model, despite showing little activity in cell-culture experiments. Overall, our results are consistent with the Fe2+-promoted uncaging of an antibacterial payload at sites of infection in an animal and lend support to recent reports indicating that extracellular pools of ferrous iron can be utilized by bacterial pathogens like P. aeruginosa during infection.
• PROCESS FOR THE PRODUCTION OF 8-CHLORO-6-(2-FLUOROPHENYL)-1-METHYL-4H-IMIDAZO 1,5-A]BENZODIAZEPINE
  申请人：PHARMACIA & UPJOHN COMPANY

  公开号：EP0918773A1

  公开（公告）日：1999-06-02