4-氧代环己烷-1-醇对甲苯磺酸酯 | 23511-04-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-氧代环己烷-1-醇对甲苯磺酸酯
• 中文别名: 4-氧代环己基(1R,2S)-1-氨基-2-乙烯基环丙烷甲酸甲酯4-甲基苯磺酸盐
• 英文名称: 4-tosyloxycyclohexanone
• 英文别名: 4-oxocyclohexyl 4-methylbenzenesulfonate；4-Tosyloxycyclohexanon；Cyclohexanone, 4-[[(4-methylphenyl)sulfonyl]oxy]-；(4-oxocyclohexyl) 4-methylbenzenesulfonate
• CAS: 23511-04-8
• 化学式: C₁₃H₁₆O₄S
• 分子量: 268.334
• InChiKey: WDKMRHPBPTUYDX-UHFFFAOYSA-N

物化性质

• 熔点：
  94-95 °C(Solv: carbon disulfide (75-15-0))
• 沸点：
  431.2±38.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2914400090

反应信息

• 作为反应物：
  描述：

  4-氧代环己烷-1-醇对甲苯磺酸酯 在 lithium iodide 作用下， 以 丙酮 为溶剂， 以47%的产率得到4-iodocyclohexanone
  参考文献：
  名称：

  Asymmetric Baeyer−Villiger Oxidations of 4-Mono- and 4,4-Disubstituted Cyclohexanones by Whole Cells of Engineered Escherichia coli

  摘要：

  Whole cells of an Escherichia coli strain that overexpresses Acinetobacter sp. NCIB 9871 cyclohexanone monooxygenase have been used for the Baeyer-Villiger oxidations of a variety of 4-mono- and 4,4-disubstituted cyclohexanones. In cases where comparisons were possible, this new biocatalytic reagent provided lactones with chemical yields and optical purities that were comparable to those obtained from the purified enzyme or a strain of bakers' yeast that expresses the same enzyme. The efficient production of cyclohexanone monooxygenase in the E. coli expression system (ca. 30% of total soluble protein) allowed these oxidations to reach completion in approximately half the time required for the engineered bakers' yeast strain. Surprisingly, 4,4-disubstituted cyclohexanones were also accepted by the enzyme, and the enantioselectivities of these oxidations could be rationalized by considering the conformational energies of bound substrates along with the enzyme's intrinsic enantioselectivity. The enzyme expressed in E. coli cells also oxidized several 4-substituted cyclohexanones bearing polar substituents, often with high enantioselectivities. In the case of 4-iodocyclohexanone the lactone was obtained in > 98% ee and its absolute configuration was assigned by X-ray crystallography. The crystal belongs to the monoclinic P2(1) space group with a = 5.7400(10), b = 6.1650(10), c = 11.377(2) Angstrom, b = 99.98(2)degrees, and Z = 2. Taken together, these results demonstrate the utility of an engineered bacterial strain in delivering useful chiral building blocks in an experimentally simple manner.

  DOI：

  10.1021/jo001292p
• 作为产物：
  描述：

  4-羟基环己酮乙二醇缩醛 在 吡啶 、 对甲苯磺酸 作用下， 以 水 为溶剂， 生成 4-氧代环己烷-1-醇对甲苯磺酸酯
  参考文献：
  名称：

  基于7-氮杂双环[2.2.1]庚烷骨架的离子液体：合成与性质

  摘要：

  基于先前开发的合成表巴替丁类似物的方法，已经合成了一系列基于 7-氮杂双环 [2.2.1] 庚烷骨架的新型离子液体。研究了含有双（三氟甲基磺酰）亚胺 (Tf2N) 和双氰胺 [N(CN)2] 阴离子的离子液体的化学和物理性质，发现它们表现出非常好的电化学和热稳定性。

  DOI：

  10.1002/ejoc.201300338

文献信息

• Homochiral ketals in organic synthesis. Diastereoselective cyclopropanation of α,β-unsaturated ketals derived from 1,4-D1-O-benzyl-l-threitol
  作者：Eugene A. Mash、Keith A. Nelson

  DOI：10.1016/s0040-4020(01)90002-x

  日期：——

  2-Cycloalken-1-one 1,4-di --benzyl -L-threitol ketals undergo efficient and diastereoselective cyclopropanation when treated with an excess of the Simmons-Smith reagent. For example, 2-cyclohexen-1-one 1,4-di --benzyl -L-threitol ketal gave in 90-98% yield a 9:1 mixture of diastereomeric cyclopropanes as established by 62.9 MHz 13C NMR spectroscopy and by hydrolysis of the mixture to (1,6)-bicyclo[4

  当用过量的Simmons-Smith试剂处理时，2-Cycloalken-1-one 1,4-二--苄基-L-苏糖醇缩酮会发生高效且非对映选择性的环丙烷化。例如，由62.9 MHz 13 C NMR光谱法和水解确定，2-环己烯-1-酮1，4-二-苄基-L-苏糖醇缩酮的收率为90-98％，为非对映体环丙烷的9：1混合物将混合物制成（1，6 ）-双环[4.1.0]庚烷-2-酮。给出了十六个其他实例，这些实例证明了2-环烯-1-酮缩酮的制备方法的一般性和可预测性，因为不幸的是，它对α，β-不饱和1,4-二-苄基-L-苏糖醇缺乏非对映选择性乙缩醛。
• 一种作为IRAK抑制剂的化合物及其制备方法和用途
  申请人：上海美悦生物科技发展有限公司

  公开号：CN111499612B

  公开（公告）日：2022-12-30

  本发明属于IRAK抑制剂领域，具体涉及适用于治疗癌症和与白细胞介素‑1受体相关激酶(IRAK)相关的炎性疾病的式(I)所示的化合物。实验表明，本发明中所披露的化合物对IRAK4激酶有良好的抑制作用，并且对其他激酶具有良好的选择性；部分化合物在动物体内显示出良好的暴露量和滞留时间；在LPS诱导的人PBMC中细胞因子TNF‑α显示了良好的抑制作用；在LPS诱导的Balb/c雌性小鼠释放TNF‑a的体内模型中也显示出良好的效果。
• FUSED HETEROCYCLIC COMPOUND, PREPARATION METHOD THEREFOR, PHARMACEUTCIAL COMPOSITION, AND USES THEREOF
  申请人：SHANGHAI YINGLI PHARMACEUTICAL CO., LTD

  公开号：US20160244432A1

  公开（公告）日：2016-08-25

  Disclosed are a fused heterocyclic compound, a preparation method therefor, a pharmaceutical composition, and uses thereof. The fused heterocyclic compound is shown in formula I, formula II, or formula III. The preparation method of the fused heterocyclic compound and/or the pharmaceutically acceptable salt thereof in the present invention comprises three synthesizing routes. The present invention also provides a pharmaceutical composition of the fused heterocyclic compound, the pharmaceutical composition containing one or more of the fused heterocyclic compound shown in formula I, formula II, or formula III, the pharmaceutically acceptable salt thereof, hydrates, solvent compounds, polymorphs and prodrugs thereof, and a pharmaceutically acceptable carrier. The present invention also relates to an application of the fused heterocyclic compound and/or the pharmaceutical composition in preparing kinase inhibitors and in preparing drugs for preventing and treating diseases related to kinase. The fused heterocyclic compound of the present invention has selective inhibition function on PI3Kδ, and can be used for preparing drugs for preventing and treating cell proliferation diseases such as cancers, infections, inflammations, or autoimmune diseases.

  揭示了一种融合杂环化合物，其制备方法，药物组合物及其用途。所述融合杂环化合物如公式I、公式II或公式III所示。本发明的所述融合杂环化合物和/或其药用可接受盐的制备方法包括三种合成途径。本发明还提供了一种包含融合杂环化合物的药物组合物，所述药物组合物含有公式I、公式II或公式III所示的一个或多个融合杂环化合物，其药用可接受盐、水合物、溶剂化合物、多型体和前药，以及药用可接受载体。本发明还涉及应用所述融合杂环化合物和/或药物组合物制备激酶抑制剂以及制备用于预防和治疗与激酶相关疾病的药物。本发明的融合杂环化合物对PI3Kδ具有选择性抑制功能，可用于制备用于预防和治疗细胞增殖性疾病如癌症、感染、炎症或自身免疫疾病的药物。
• Unified Oxidation Protocol for the Synthesis of Carbonyl Compounds Using a Manganese Catalyst
  作者：Masayuki Inoue、Shin Kamijo、Yuuki Amaoka

  DOI：10.1055/s-0029-1218809

  日期：2010.7

  C-H oxidation of alkyl ethers and benzylic compounds to generate the corresponding ketones. Alternatively, the water-soluble inorganic salt KHSO5 in combination with the Mn catalyst was used to oxidize alcohols to ketones or carboxylic acids. Importantly, the Mn catalyst/KHSO5 system eliminates technical difficulties associated with the isolation of carboxylic acid products. All the oxidations presented

  我们已经开发出用于将醚，苄基化合物和醇氧化为羰基化合物的统一协议。该方案使用催化量的四水合氯化锰（II）和4,4'，4'-三（叔丁基）-2,2'：6'，2''-吡啶和化学计量的任何一种间氯过苯甲酸（MCPBA）或过氧硫酸氢钾（KHSO 5）。由Mn催化剂和MCPBA组成的试剂体系使烷基醚和苄基化合物的化学选择性sp³CH氧化生成相应的酮。或者，水溶性无机盐KHSO 5与Mn催化剂结合使用可将醇氧化为酮或羧酸。重要的是，Mn催化剂/ KHSO 5系统消除了与分离羧酸产物相关的技术难题。本专题文章中提出的所有氧化反应均在有氧气氛中于低于环境温度的温度下进行，因此可用于复杂有机分子的实际合成中。 催化-氧化-醚-醇-酮-羧酸
• Heterocylic antiviral compounds
  申请人：Rotstein David Mark

  公开号：US20080249087A1

  公开（公告）日：2008-10-09

  This invention relates to piperidine derivatives of formula I wherein R 1 , R 2 , R 3 and R 4 are as defined herein useful in the treatment of a variety of disorders, including those in which the modulation of CCR5 receptors is implicated. Disorders that may be treated or prevented by the present derivatives include HIV and genetically related retroviral infections (and the resulting acquired immune deficiency syndrome, AIDS), rheumatoid arthritis, solid organ transplant reject (graft vs. host disease), asthma and COPD.

  这项发明涉及式I的哌啶衍生物，其中R1、R2、R3和R4如本文所定义，在治疗各种疾病中有用，包括那些涉及CCR5受体调节的疾病。目前这些衍生物可以治疗或预防的疾病包括HIV和遗传相关的逆转录病毒感染（以及由此导致的获得性免疫缺陷综合症，艾滋病），类风湿性关节炎，固体器官移植排斥（移植物抗宿主病），哮喘和慢性阻塞性肺病（COPD）。