1-(4-(苄氧基)-2-甲基苯基)乙酮 | 608119-82-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(4-(苄氧基)-2-甲基苯基)乙酮
• 英文名称: 1-(4-(benzyloxy)-2-methylphenyl)ethanone
• 英文别名: 1-{2-methyl-4-[(phenylmethyl)oxy]phenyl}ethanone；1-[4-(benzyloxy)-2-methylphenyl]ethanone；1-(4-benzyloxy-2-methylphenyl)-ethanone；4-benzyloxy-2-methyl-acetophenone；4-benzyloxy-2-methylacetophenone；1-(2-methyl-4-phenylmethoxyphenyl)ethanone
• CAS: 608119-82-0
• 化学式: C₁₆H₁₆O₂
• mdl: MFCD03721541
• 分子量: 240.302
• InChiKey: UGIGSWZYZVRDAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.187
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-(苄氧基)-2-甲基苯基)乙酮 在 盐酸 、 Oxone 、 正丁基锂 、 草酰氯 、 对甲苯磺酸 、 N,N-二甲基甲酰胺 、 sodium bromide 作用下， 以 四氢呋喃 、 氯仿 、 水 、 丙酮 、 甲苯 为溶剂， 生成 2,3,4,6-tetra-O-benzyl-1-C-[2-(benzyloxy)-5-formyl-4-methylphenyl]-5-thio-D-glucopyranose
  参考文献：
  名称：

  Discovery of a potent, low-absorbable sodium-dependent glucose cotransporter 1 (SGLT1) inhibitor (TP0438836) for the treatment of type 2 diabetes

  摘要：

  The design and synthesis of a novel class of low-absorbable SGLT1 inhibitors are described. To achieve low absorption in the new series, we performed an optimization study based on a strategy to increase TPSA. Fortunately, the optimization of an aglycon moiety and a side chain of the distal aglycon moiety led to the identification of compound 30b as a potent and low-absorbable SGLT1 inhibitor. Compound 30b showed a desirable PK profile in Sprague-Dawley (SD) rats and a favorable glucose-lowering effect in diabetic rats.

  DOI：

  10.1016/j.bmcl.2018.09.035
• 作为产物：
  描述：

  4'-羟基-2'-甲基苯乙酮 、 溴甲苯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 1-(4-(苄氧基)-2-甲基苯基)乙酮
  参考文献：
  名称：

  1,4-钯Shift / C（sp 3）–H活化策略用于五元环的远程构建

  摘要：

  如图1所示，n-金属转移是一种优雅的替代方法，可以使简单前体中的远程C-H键实现功能化。在这项工作中，我们报告了一个新颖而简单的Pd 0催化的多米诺骨牌反应，涉及1，4-钯的转变和C（sp 3）-H的活化并导致（稠合的）五元环。该方法可以使用各种有价值的亚芳基γ-内酰胺和茚满酮，并被用于（-）-吡咯烷的形式合成。

  DOI：

  10.1021/acs.orglett.9b00187

文献信息

• [EN] (THIO)MORPHOLINE DERIVATIVES AS S1P MODULATORS<br/>[FR] DÉRIVÉS DE (THIO)MORPHOLINE MODULATEURS DE S1P
  申请人：ABBOTT HEALTHCARE PRODUCTS BV

  公开号：WO2011023795A1

  公开（公告）日：2011-03-03

  The present invention relates to (thio)morpholine derivatives of the formula (I), wherein R1 is selected from cyano, (2-4C)alkynyl, (1-4C)alkyl, (3-6C)cycloalkyl, (4-6C)cycloalkenyl, (6-8C)bicycloalkyl, (8-10C)bicyclic group, each optionally substituted with (1-4C)alkyl, phenyl, biphenyl, naphthyl, each optionally substituted with one or more substituents independently selected from halogen, (1-4C)alkyloptionally substituted with one or more fluoro atoms, (2-4C)alkynyl, (1-4C)alkoxy optionally substituted with one or more fluoro atoms,amino, di(1-4C)alkylamino, -SO2-(1-4C)alkyl, -CO-(1-4C)alkyl, -CO-O-(1-4C)alkyl, -NH-CO-(1-4C)alkyl and (3-6C)cycloalkyl, phenyl substituted with phenoxy, benzyl, benzyloxy, phenylethyl or monocyclic heterocycle, each optionally substituted with (1-4C)alkyl, monocyclic heterocycle optionally substituted with halogen, (1-4C)alkyl or with phenyl optionally substituted with (1-4C)alkyl, and bicyclic heterocycle optionally substituted with (1-4C)alkyl; A is selected from -CO-O-, -O-CO-, -NH-CO-, -CO-NH, -C=C-, -CCH3-O- and the linking group –Y-(CH2)n-X- wherein Y is attached to R1 and selected from a bond, -O-, -S-, -SO-, -SO2-, -CH2-O-, -CO-, -O-CO-, -CO-O-, -CO-NH-, -NH-CO-, -C=C-and -C≡C-; n is an integer from 1 to 10; and X is attached to the phenylene / pyridyl group and selected from a bond, -O-, -S-, -SO-, -SO2 -, -NH, -CO-, -C=C-and -C≡C-; ring structure B optionally contains one nitrogen atom; R2 is H, (1-4C)alkyl optionally substituted with one or more fluoro atoms, (1-4C)alkoxy optionally substituted with one or more fluoro atoms, or halogen; and R3 is (1-4C)alkylene-R5 wherein the alkylene group may be substituted with (CH2)2 to form a cyclopropyl moiety or one or two halogen atoms, or R3 is is (3-6C)cycloalkylene-R5 or -CO-CH2-R5, wherein R5 is -OH, -PO3H2, -OPO3H2, -COOH, -COO(1-4C)alkyl or tetrazol-5-yl; R4 is H or (1-4C)alkyl; R6 is one or more substituents independently selected from H, (1-4C)alkyl or oxo; W is -O-, -S-, -SO- or -SO2-; or a pharmaceutically acceptable salt, a solvate or hydrate thereof; with the proviso that the derivative of formula (I) is not 2-(4-ethylphenyl)-4-morpholinoethanol or 4-[4-(2-hydroxyethyl)-2-morpholinyl]benzeneacetonitrile or a pharmaceutically acceptable salt, a solvate or hydrate thereof. The compounds of the invention have affinity to S1P receptors and may be used in the treatment, alleviation or prevention of S1P receptor mediated diseases and conditions.

  本发明涉及公式（I）的（硫）吗啉衍生物，其中R1从氰基，（2-4C）炔基，（1-4C）烷基，（3-6C）环烷基，（4-6C）环烯基，（6-8C）双环烷基，（8-10C）双环基团中选择，每个基团可选择地取代为（1-4C）烷基，苯基，联苯基，萘基，每个基团可选择地取代为一个或多个取代基，独立选择自卤素，（1-4C）烷基可选择地取代为一个或多个氟原子，（2-4C）炔基，（1-4C）氧烷基可选择地取代为一个或多个氟原子，氨基，二（1-4C）烷基氨基，-SO2-（1-4C）烷基，-CO-（1-4C）烷基，-CO-O-（1-4C）烷基，-NH-CO-（1-4C）烷基和（3-6C）环烷基，苯基取代为苯氧基，苄基，苄氧基，苯乙基或单环杂环烃，每个基团可选择地取代为（1-4C）烷基，单环杂环烃可选择地取代为卤素，（1-4C）烷基或取代为苯基的苯基，可选择地取代为（1-4C）烷基，和双环杂环烃可选择地取代为（1-4C）烷基；A从-CO-O-，-O-CO-，-NH-CO-，-CO-NH，-C=C-，-CCH3-O-和连接基-Y-（CH2）n-X-中选择，其中Y连接到R1并从键，-O-，-S-，-SO-，-SO2-，-CH2-O-，-CO-，-O-CO-，-CO-O-，-CO-NH-，-NH-CO-，-C=C-和-C≡C-中选择；n是1到10的整数；X连接到苯基/吡啶基团并从键，-O-，-S-，-SO-，-SO2-，-NH，-CO-，-C=C-和-C≡C-中选择；环结构B可选择地含有一个氮原子；R2是H，（1-4C）烷基可选择地取代为一个或多个氟原子，（1-4C）氧烷基可选择地取代为一个或多个氟原子，或卤素；R3是（1-4C）烷基-R5，其中烷基基团可取代为（CH2）2形成环丙基基团或一个或两个卤素原子，或R3是（3-6C）环烷基-R5或-CO-CH2-R5，其中R5是-OH，-PO3H2，-OPO3H2，-COOH，-COO（1-4C）烷基或四唑-5-基；R4是H或（1-4C）烷基；R6是一个或多个取代基，独立选择自H，（1-4C）烷基或氧代基；W是-O-，-S-，-SO-或-SO2-；或其药学上可接受的盐，溶剂或水合物；但是，公式（I）的衍生物不是2-（4-乙基苯基）-4-吗啉乙醇或4-[4-（2-羟乙基）-2-吗啉基]苯乙腈或其药学上可接受的盐，溶剂或水合物。本发明的化合物具有对S1P受体的亲和力，可用于治疗、缓解或预防S1P受体介导的疾病和症状。
• <i>p</i>-Hydroxyphenacyl photoremovable protecting groups — Robust photochemistry despite substituent diversity
  作者：Richard S. Givens、Kenneth Stensrud、Peter G. Conrad、Abraham L. Yousef、Chamani Perera、Sanjeewa N. Senadheera、Dominik Heger、Jakob Wirz

  DOI：10.1139/v10-143

  日期：2011.2

  A broadly based investigation of the effects of a diverse array of substituents on the photochemical rearrangement of p-hydroxyphenacyl esters has demonstrated that common substituents such as F, MeO, CN, CO₂R, CONH₂, and CH₃have little effect on the rate and quantum efficiencies for the photo-Favorskii rearrangement and the release of the acid leaving group or on the lifetimes of the reactive triplet state. A decrease in the quantum yields across all substituents was observed for the release and rearrangement when the photolyses were carried out in buffered aqueous media at pHs that exceeded the ground-state pK_aof the chromophore where the conjugate base is the predominant form. Otherwise, substituents have only a very modest effect on the photoreaction of these robust chromophores.

  一项关于各种取代基对对羟基苯乙酯光化学重排影响的广泛研究表明，常见取代基（如 F、MeO、CN、CO2R、CONH2 和 CH3）对光-Favorskii 重排和酸离去基团释放的速率和量子效率影响很小，对反应三重态的寿命影响也很小。当光解在缓冲水介质中进行时，pH 值超过发色团的基态 pKao（其中共轭碱是主要形式），则释放和重排的量子产率在所有取代基中都会降低。否则，取代基对这些坚固发色团的光反应影响很小。
• Medicinal arylethanolamine compounds
  申请人：Coe Mary Diane

  公开号：US20060205790A1

  公开（公告）日：2006-09-14

  The present invention relates to novel compounds of formula (I), and salts, solvates and physiologically acceptable derivatives thereof, to a process for their manufacture, to pharmaceutical compositions containing them, and to their use in therapy, in particular their use in the prophylaxis and treatment of respiratory diseases.

  本发明涉及化合物的新型公式(I)，以及其盐，溶剂合物和生理上可接受的衍生物，其制备方法，含有它们的药物组合物，以及它们在治疗中的应用，特别是在预防和治疗呼吸系统疾病方面的应用。
• FXR AGONISTS
  申请人：Bell Michael Gregory

  公开号：US20090270460A1

  公开（公告）日：2009-10-29

  Compounds of formula wherein variables are as defined herein and their pharmaceutical compositions and methods of use are disclosed as useful for treating dyslipidemia and related diseases.

  本发明公开了化学式为所定义变量的化合物及其制药组合物和使用方法，用于治疗血脂异常及相关疾病。
• C-PHENYL GLYCITOL COMPOUND
  申请人：Kakinuma Hiroyuki

  公开号：US20100022460A1

  公开（公告）日：2010-01-28

  Provided is a novel C-phenyl glycitol compound that may serve as a prophylactic or therapeutic agent for diabetes by inhibiting both SGLT1 activity and SGLT2 activity, thereby exhibiting a glucose absorption suppression action and a urine glucose excretion action. A C-phenyl glycitol compound represented by Formula (I) below or a pharmaceutically acceptable salt thereof or a hydrate thereof wherein R 1 and R 2 are the same or different and represent a hydrogen atom, a hydroxyl group, a C 1-6 alkyl group, a C 1-6 alkoxy group or a halogen atom, R 3 is a hydrogen atom, a C 1-6 alkyl group, a C 1-6 alkoxy group or a halogen atom, Y is a C 1-6 alkylene group, —O—(CH 2 )n— (n is an integer of 1 to 4) or a C 2-6 alkenylene group, provided that when Z is —NHC(═NH)NH 2 or —NHCON(R B )R C , n is not 1, Z is —CONHR A , —NHC(═NH)NH 2 or —NHCON(R B )R C ,

  提供的是一种新型C-苯基甘露醇化合物，可以作为预防或治疗糖尿病的药物，通过抑制SGLT1活性和SGLT2活性，从而表现出抑制葡萄糖吸收和尿液葡萄糖排泄的作用。该化合物表示为以下式子（I）的C-苯基甘露醇化合物，或其药学上可接受的盐或水合物，其中R1和R2相同或不同，表示氢原子、羟基、C1-6烷基、C1-6烷氧基或卤素原子，R3表示氢原子、C1-6烷基、C1-6烷氧基或卤素原子，Y表示C1-6烷基、-O-(CH2)n-（n为1至4的整数）或C2-6烯基烷基，但当Z为-NHC（=NH）NH2或-NHCON（RB）RC时，n不为1，Z为CONHRA，-NHC（=NH）NH2或-NHCON（RB）RC。