5-(tert-butyldimethylsilanyloxy)isophthalic acid dimethyl ester | 182629-24-9

• 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: 5-(tert-butyldimethylsilanyloxy)isophthalic acid dimethyl ester
• 英文别名: dimethyl 5-{[(1,1-dimethylethyl)dimethylsilyl]oxy}benzene-1,3-dicarboxylate；dimethyl 5-[tert-butyl(dimethyl)silyl]oxybenzene-1,3-dicarboxylate；dimethyl 5-(tert-butyldimethylsilyloxy)isophthalate；Dimethyl 5-{[tert-butyl(dimethyl)silyl]oxy}isophthalate
• CAS: 182629-24-9
• 化学式: C₁₆H₂₄O₅Si
• 分子量: 324.449
• InChiKey: JTTKCSGXFPZXQJ-UHFFFAOYSA-N

物化性质

• 沸点：
  368.6±32.0 °C(Predicted)
• 密度：
  1.054±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.64
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(tert-butyldimethylsilanyloxy)isophthalic acid dimethyl ester 在 potassium fluoride 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.67h， 生成 3-羟基-5-(羟甲基)苯甲酸甲酯
  参考文献：
  名称：

  含内羧基的新型空间松弛树突的合成与性质

  摘要：

  我们合成了一系列具有多达 14 个内部羧基的新树突。这些树突由支链单元和带有羧基的间隔单元组成。生长反应（苄醚键的形成）在几个小时内完成，这表明在树枝状骨架的“焦点”点具有高反应性。内部酯基的最终脱保护也顺利进行。这些高反应性归因于间隔单元的存在，这导致这些分子的空间松弛构象。根据馏分，树枝的羧酸盐形式在 THF/水混合溶剂中产生正胶束和反胶束。

  DOI：

  10.1246/bcsj.77.993
• 作为产物：
  描述：

  5-羟基间苯二甲酸 在 硫酸 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 5-(tert-butyldimethylsilanyloxy)isophthalic acid dimethyl ester
  参考文献：
  名称：

  Davies, Philip J.; Veldman, Nora; Grove, David M., Angewandte Chemie, 1996, vol. 108, # 17, p. 2078 - 2081

  摘要：

  DOI：

文献信息

• [EN] EFFLUX-PUMP INHIBITORS AND THERAPEUTIC USES THEREOF<br/>[FR] INHIBITEURS DE LA POMPE À EFFLUX ET UTILISATIONS THÉRAPEUTIQUES CORRESPONDANTES
  申请人：BASILEA PHARMACEUTICA AG

  公开号：WO2016198691A1

  公开（公告）日：2016-12-15

  The present invention relates to compounds of formula I or pharmaceutically acceptable salt, solvate or hydrate thereof, wherein ASC is -N(R8)(R9)ASC-1 ASC-1 is Ring A represents a 4- to 6-membered saturated ring containing carbon atoms as ring members in addition to the nitrogen atom and wherein one CH2 moiety in ring A is optionally replaced by CH(R21) and wherein one carbon atom in ring A that is not adjacent to the nitrogen atom is optionally replaced by O, and wherein ring A is connected to X via a carbon atom; X represents a bond, -CH2- or -C(=O)-; ARl, AR2 represent independently phenyl or a 5- to 6- membered heteroaryl ring containing one to three heteroatoms selected from O, S and N, wherein AR1 is connected to LI via a carbon atom, and wherein AR2 is connected to L1 and L2 via a carbon atom; R1, R2, R3 represent independently hydrogen, halogen, cyano, hydroxyl, C1-C6alkyl, C1-C6haloalkyl, C3- C8cycloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, -C1-C6alkylene-N(R12)R13, -N(R12)R13, -C(O)OR11l, - C(O)N(R12)R13, -S(O)OR11 or phenyl; R4 represents hydroxyl, hydrogen, halogen, nitro, cyano, amino, C1-C6alkyl optionally substituted by 1 to 5 R14, C2-C6alkenyl optionally substituted by 1 to 5 R14, C2-C6alkynyl optionally substituted by 1 to 5 R14, C1-C6alkoxy optionally substituted by 1 to 5 R14, C2-C6alkenyloxy optionally substituted by 1 to 5 R14, C2-C6alkynyloxy optionally substituted by 1 to 5 R14, -C(O)OR15, -CHO, -C(O)N(R16)R17, -C1- C6alkylene-N(R9)(R16)R17, -O-Cycle-P or -O-Cycle-Q; R5, R6, R7 represent independently hydrogen, halogen, cyano, Cl-C6alkyl, C1-C6haloalkyl, Cl-C6alkoxy or C1-C6haloalkoxy; R8 represents hydrogen, methyl or ASC-1; R9 is methyl or absent, and wherein when R9 is present the respective nitrogen atom carries a positive charge; R10 represents hydrogen or methyl; Rl11 represents independently at each occurrence hydrogen or C1-C6alkyl; R12, R13 represent independently at each occurrence hydrogen or C1-C6alkyl; R14 represents independently at each occurrence halogen, cyano, hydroxyl, C1-C6alkoxy, C1-C6haloalkoxy, C3-C8cycloalkyl, -C(O)OR11, -CHO, -C(O)N(R12)R13, -C1-C6alkylene-N(R12)R13, Cycle-P, O-Cycle-P, Cycle-Q or O-Cycle-Q; Cycle-P represents independently at each occurrence a saturated or partially unsaturated C3-C8 carbocyclic ring optionally substituted by 1 to 3 R18, or a saturated or partially unsaturated C3-C8 heterocyclic ring optionally substituted by 1 to 3 Rl 8 containing carbon atoms as ring members and one or two ring members independently selected from N(R9)(R12), N(R9) and O; Cycle-Q represents independently at each occurrence phenyl optionally substituted by 1 to 3 R19 or a 5- to 6-membered heteroaryl ring containing one to four heteroatoms selected from O, S and N, optionally substituted by 1 to 3 R19; R15 represents independently at each occurrence hydrogen or C1-C6alkyl optionally substituted by 1 to 5 R14; R16 and R17 represent independently at each occurrence hydrogen or C1-C6alkyl optionally substituted by 1 to 5 R14; R18 and R19 represent independently at each occurrence halogen, cyano, hydroxyl, oxo, amino, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, Cl-C4haloalkoxy or -CO(O)R11; R20 represents independently at each occurrence hydrogen or methyl; R21 represents N(R20)2 or CH2-N(R20)2; LI represents -CH=CH-, -CH2-O-, -O-CH2-, -CH2-O-CH2-,-CH2-S-, -S-CH2-, -CH2-S(O)-, -CH2-S(O2)-, -S(O)-CH2-; -S(O2)-CH2-, -C(CH3)(CH3)-, -C(=O)-NH-, -NH-C(=O)-, -CH2-CH2-, -CH=CH-CH2-, - CH2-NH-C(=O)-, -C(=O)-NH-CH2, -C≡C-, -S(O2)-NH-CH2-, -S(02)-NH, -O-CH2-CH2-O-, -O-, -NH- CH2-, -CH2-NH-, -CH2-CH2-O-, or -NH-C(=O)-CH2-O-, or a bond; L2 represents Cl-C7alkylene, wherein one or more CH2 moieties in the alkylene are optionally replaced independently by -N(R9)(R20)-, -CH(N(R9)(R20)(R20))-, or -C(=0)-, wherein within L2 there are no adjacent C(=O) moieties or adjacent -N(R9)(R20)- moieties, and wherein the terminal moiety of L2 is not - N(R9)(R20)-, or L2 represents -O-C1-C6alkylene-, or L2 represents a bond, providing that X represents - CH2- when L2 is a bond; as well as methods of using the compounds of formula I for treating or preventing bacterial infections.

  本发明涉及以下公式I的化合物或其药学上可接受的盐、溶剂或水合物，其中ASC为-N(R8)(R9)ASC-1，ASC-1为环A，表示一个含有碳原子的4-至6-成员饱和环，除氮原子外还包含碳原子，并且环A中的一个CH2基团可以选择性地被CH(R21)取代，环A中的一个非邻氮原子的碳原子可以选择性地被氧取代，环A通过一个碳原子连接到X；X表示一个键，-CH2-或-C(=O)-；AR1、AR2独立表示苯基或一个含有1至3个氧、硫和氮的杂环的5至6-成员环，其中AR1通过一个碳原子连接到L1，AR2通过一个碳原子连接到L1和L2；R1、R2、R3独立表示氢、卤素、氰基、羟基、C1-C6烷基、C1-C6卤代烷基、C3-C8环烷基、C1-C6烷氧基、C1-C6卤代烷氧基、-C1-C6烷基-N(R12)R13、-N(R12)R13、-C(O)OR11l、-C(O)N(R12)R13、-S(O)OR11或苯基；R4表示羟基、氢、卤素、硝基、氰基、氨基、C1-C6烷基，可选地被1至5个R14取代，C2-C6烯基，可选地被1至5个R14取代，C2-C6炔基，可选地被1至5个R14取代，C1-C6烷氧基，可选地被1至5个R14取代，C2-C6烯氧基，可选地被1至5个R14取代，C2-C6炔氧基，可选地被1至5个R14取代，-C(O)OR15，-CHO，-C(O)N(R16)R17，-C1-C6烷基-N(R9)(R16)R17，-O-Cycle-P或-O-Cycle-Q；R5、R6、R7独立表示氢、卤素、氰基、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基或C1-C6卤代烷氧基；R8表示氢、甲基或ASC-1；R9为甲基或不存在，当R9存在时，相应的氮原子带有正电荷；R10表示氢或甲基；Rl11独立表示每次出现的氢或C1-C6烷基；R12、R13独立表示每次出现的氢或C1-C6烷基；R14独立表示每次出现的卤素、氰基、羟基、C1-C6烷氧基、C1-C6卤代烷氧基、C3-C8环烷基、-C(O)OR11、-CHO、-C(O)N(R12)R13、-C1-C6烷基-N(R12)R13、Cycle-P、O-Cycle-P、Cycle-Q或O-Cycle-Q；Cycle-P独立表示每次出现的饱和或部分不饱和的C3-C8碳环，可选地被1至3个R18取代，或者可选地被1至3个Rl 8取代的饱和或部分不饱和的C3-C8杂环，含有碳原子作为环成员，并且一个或两个环成员独立选择自N(R9)(R12)、N(R9)和O；Cycle-Q独立表示每次出现的苯环，可选地被1至3个R19取代，或者一个含有1至4个氧、硫和氮的5至6-成员杂环，可选地被1至3个R19取代；R15独立表示每次出现的氢或C1-C6烷基，可选地被1至5个R14取代；R16和R17独立表示每次出现的氢或C1-C6烷基，可选地被1至5个R14取代；R18和R19独立表示每次出现的卤素、氰基、羟基、氧、氨基、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、Cl-C4卤代烷氧基或-CO(O)R11；R20独立表示每次出现的氢或甲基；R21表示N(R20)2或CH2-N(R20)2；LI表示-CH=CH-、-CH2-O-、-O-CH2-、-CH2-O-CH2-、-CH2-S-、-S-CH2-、-CH2-S(O)-、-CH2-S(O2)-、-S(O)-CH2-、-S(O2)-CH2-、-C(CH3)(CH3)-、-C(=O)-NH-、-NH-C(=O)-、-CH2-CH2-、-CH=CH-CH2-、-CH2-NH-C(=O)-、-C(=O)-NH-CH2、-C≡C-、-S(O2)-NH-CH2-、-S(02)-NH、-O-CH2-CH2-O-、-O-、-NH-CH2-、-CH2-NH-、-CH2-CH2-O-或-NH-C(=O)-CH2-O-、或一个键；L2表示Cl-C7烷基，其中烷基中的一个或多个CH2基团可以选择性地独立地被-N(R9)(R20)-、-CH(N(R9)(R20)(R20))-或-C(=0)-取代，在L2内没有相邻的C(=O)基团或相邻的-N(R9)(R20)-基团，并且L2的末端基团不是-N(R9)(R20)-，或者L2表示-O-C1-C6烷基-，或者L2表示一个键，只要X在L2是一个键时表示-CH2-；以及使用公式I的化合物治疗或预防细菌感染的方法。
• Supramolecular Side-Chain Functionalized Polymers: Synthesis and Self-Assembly Behavior of Polynorbornenes Bearing Pd^II SCS Pincer Complexes
  作者：Marcus Weck、Joel Pollino

  DOI：10.1055/s-2002-32534

  日期：——

  A new polynorbornene bearing palladated SCS pincer complexes at each repeat unit has been synthesized using ring-opening metathesis polymerization. Small mesogenic molecules possessing nitrile or pyridine-based anchoring units are instantaneously and quantitatively coordinated to the palladium center in one simple self-assembly step giving rise to a densely functionalized polymer. These results suggest that the coordination of mesogenic small molecules onto the polymer scaffold can provide a simple and efficient route to a variety of materials.

  一种新型聚萘并烯的合成，具有在每个重复单元上承载的钯化SCS夹持体，采用开环复分解聚合（ROMP）法制备而成。小型介晶分子具有腈或基于吡啶的锚定单元，在一个简单的自组装步骤中即时且定量地与钯中心配位，从而形成了一种高度功能化的聚合物。这些结果表明，小型介晶分子在聚合物支架上的配位可以为各种材料提供一种简单而高效的途径。
• Self-assembly of hyperbranched spheres
  作者：Wilhelm T. S. Huck、Frank C. J. M. van Veggel、David N. Reinhoudt

  DOI：10.1039/a608577f

  日期：——

  A new type of building block with two coordinatively unsaturated palladium centres has been described that self-assembles in nitromethane solution and disassembles when acetonitrile is added. The resulting hyperbranched, organopalladium spheres have a remarkably narrow size distribution as was evidenced by light-scattering, AFM and TEM measurements. Variation of the structure of the building blocks showed the possibility to vary the size of the self-assembled spheres between 100 and 400 nm.

  一种新型的建筑块已被描述，其具有两个配位不饱和的钯中心，并在硝基甲烷溶液中自组装，当加入乙腈时则解体。生成的超支化有机钯 spheres 具有显著狭窄的尺寸分布，这通过光散射、原子力显微镜（AFM）和透射电子显微镜（TEM）测量得到了证实。建筑块结构的变化显示了自组装 spheres 的尺寸可以在100至400纳米之间变化的可能性。
• Synthesis of Amphiphilic Fullerene Derivatives and Their Incorporation inLangmuir andLangmuir-Blodgett Films
  作者：Delphine Felder、Manuel Gutiérrez Nava、Maria del Pilar Carreón、Jean-François Eckert、Michaël Luccisano、Corinne Schall、Patrick Masson、Jean-Louis Gallani、Benoît Heinrich、Daniel Guillon、Jean-François Nierengarten

  DOI：10.1002/1522-2675(200201)85:1<288::aid-hlca288>3.0.co;2-i

  日期：2002.1

  While no films could be obtained from compound 19 with no polar head group, all the corresponding amphiphilic fullerene bis-adducts showed good spreading characteristics and reversible behavior upon successive compression/expansion cycles. The encapsulation of the fullerene in a cyclic addend surrounded by four long alkyl chains is, therefore, an efficient strategy to prevent the irreversible aggregation

  通过用丙二酸单酯 5-7 酯化获得的丙二酸酯或双丙二酸酯衍生物对 [5,6] 富勒烯-C60-Ih (C60) 进行官能化制备各种两亲富勒烯衍生物。环丙富勒烯 10 是通过将 6 的羧酸官能团保护为叔丁酯，然后将 Bingel 添加到 C60 和脱保护步骤（方案 2）而获得的。还尝试在宾格尔条件下直接由丙二酸单酯 6 制备 10。令人惊讶的是，形成了相应的 3'-iodo-3'H-cyclopropa[1,9][5,6]fullerene-C60-Ih-3'-carboxylate 11 而不是 10（方案 3）。通过分别从丙二酸单酯 13 和 14 制备 15 和 16 证实了这种新反应的一般特征（方案 4）。所有其他两亲富勒烯衍生物都是利用 Diederich 及其同事开发的多功能区域选择性反应制备的，该反应通过在 C 球上与双丙二酸衍生物在双宾格尔中的环化反应生成 C60 的大环双加合物环丙烷化。分别由二醇
• [EN] NITRIC OXIDE RELEASING SELECTIVE CYCLOOXYGENASE-2 INHIBITORS<br/>[FR] INHIBITEURS SELECTIFS DE LA CYCLO-OXYGENASE-2 LIBERANT DE L'OXYDE NITRIQUE
  申请人：MERCK FROSST CANADA INC

  公开号：WO2004037798A1

  公开（公告）日：2004-05-06

  The invention encompasses novel compounds of Formula (I) and Formula (II), which are nitric oxide-releasing prodrugs useful in the treatment of cyclooxygenase-2 mediated diseases. The invention also encompasses certain pharmaceutical compositions and methods for treatment of cyclooxygenase-2 mediated diseases comprising the use of compounds of Formula (I) or Formula (II). The above compounds may be used as a combination therapy with low-dose aspirin to treat chronic cyclooxygenase-2 mediated diseases or conditions while simultaneously reducing the risk of thrombotic cardiovascular events.

  该发明涵盖了式(I)和式(II)的新化合物，这些化合物是一氧化氮释放前药，在治疗环氧合酶-2介导的疾病方面非常有用。该发明还涵盖了某些药物组合以及治疗环氧合酶-2介导的疾病的方法，包括使用式(I)或式(II)的化合物。上述化合物可以与低剂量阿司匹林联合治疗慢性环氧合酶-2介导的疾病或症状，同时降低血栓性心血管事件的风险。