methyl 3-bromo-4-(((trifluoromethyl)sulfonyl)oxy)benzoate | 1233244-03-5

• 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: methyl 3-bromo-4-(((trifluoromethyl)sulfonyl)oxy)benzoate
• 英文别名: Methyl 3-bromo-4-(trifluoromethylsulfonyloxy)benzoate；methyl 3-bromo-4-(trifluoromethylsulfonyloxy)benzoate
• CAS: 1233244-03-5
• 化学式: C₉H₆BrF₃O₅S
• 分子量: 363.109
• InChiKey: SXPFOOWLNGIQOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 3-bromo-4-(((trifluoromethyl)sulfonyl)oxy)benzoate 、 butane,chlorozinc(1+) 在 Di-MU-碘二(三-t-丁基膦基)二钯(I) 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 0.08h， 以79%的产率得到methyl 3-butyl-4-(trifluoromethylsulfonyloxy)benzoate
  参考文献：
  名称：

  钯(I)二聚体能够在空气中对三氟甲磺酸酯和氯化物进行极其快速的化学选择性烷基化芳基溴化物。

  摘要：

  本文公开的是在 COTf、C-Cl 和其他潜在反应性官能团存在下，使用空气稳定、水分稳定和热稳定的双核 PdI 催化剂，对 C-Br 键进行第一个常规化学和位点选择性烷基化，[ Pd(μ-I)PtBu3]2 。溴选择性与底物和竞争反应位点的相对位置无关，因此完全可预测。在室温和开瓶反应条件下以极高的速度（<5 分钟反应时间）引入伯烷基链和仲烷基链。

  DOI：

  10.1002/anie.201701691
• 作为产物：
  描述：

  三氟甲磺酸酐 、 3-溴-4-羟基苯甲酸甲酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以98%的产率得到methyl 3-bromo-4-(((trifluoromethyl)sulfonyl)oxy)benzoate
  参考文献：
  名称：

  快速室温，空气中钯（I）催化实现的聚（假）卤代芳烃的化学选择性Csp2-Csp2偶联。

  摘要：

  尽管Pd0催化的偶联反应中的化学选择性通常是不直观的，并且是配体/催化剂，底物和反应条件之间复杂相互作用的结果，但我们在此报告了一种基于PdI的通用方法，该方法可实现事先可预测的化学选择性Csp2- Csp2在C-Br处的偶联优先于C-OTf和C-Cl键，而与底物的电子或空间偏压无关。CC键的形成非常快（在RT下<5分钟），并在开瓶条件下被空气和水分稳定的PdI二聚体催化。

  DOI：

  10.1002/anie.201609635

文献信息

• InCl₃-Catalyzed Synthesis of 1,2-Dimetallic Compounds by Direct Insertion of Aluminum or Zinc Powder
  作者：Tobias D. Blümke、Thomas Klatt、Konrad Koszinowski、Paul Knochel

  DOI：10.1002/anie.201205169

  日期：2012.9.24

  In‐sertion of metal: Catalytic amounts of InCl3 allow the insertion of aluminum and zinc into aromatic 1,2‐dibromides or 1,2‐bromotriflates (see scheme). These 1,2‐dimetallic species can undergo Cu or Pd‐catalyzed acylations, allylations, or cross‐couplings.

  金属的插入：催化量的InCl 3可使铝和锌插入芳族1,2-二溴化物或1,2-溴三氟甲磺酸酯中（请参阅方案）。这些1,2-双金属物种可能会经历Cu或Pd催化的酰化，烯丙基化或交叉偶联。
• Synthesis of 1,2-Dimetallic Compounds via Direct Insertion of Zinc Powder in the Presence of InCl3: Synthesis of ortho-Bis-functionalized Aromatics
  作者：Paul Knochel、Thomas Klatt、Tobias Blümke、Maximilian Ganiek

  DOI：10.1055/s-0033-1340106

  日期：——

  1,2-dizinc reagents can be prepared by an indium-catalyzed insertion of zinc powder into aromatic 1,2-dibromides or 1-bromo-2-triflates. These 1,2-dimetallics undergo Cu- or Pd-catalyzed acylations, allylations, or cross couplings. A variety of functionalized 1,2-dizinc reagents can be prepared by an indium-catalyzed insertion of zinc powder into aromatic 1,2-dibromides or 1-bromo-2-triflates. These

  摘要 可以通过铟催化将锌粉插入芳族1,2-二溴化物或1-溴-2-三氟甲磺酸酯中来制备各种功能化的1,2-二嗪试剂。这些1,2-二金属化合物经过Cu或Pd催化的酰化，烯丙基化或交叉偶联。 可以通过铟催化将锌粉插入芳族1,2-二溴化物或1-溴-2-三氟甲磺酸酯中来制备各种功能化的1,2-二嗪试剂。这些1,2-二金属化合物经过Cu或Pd催化的酰化，烯丙基化或交叉偶联。
• 1,2,4-oxadiazole derivatives and their therapeutic use
  申请人：Laboratorios Almirall, S.A.

  公开号：EP2202232A1

  公开（公告）日：2010-06-30

  New derivatives of general formula (I), or pharmaceutically acceptable salts or N-oxides thereof wherein, A is selected from the group consisting of -N-, -O- and -S-; B and C are independently selected from the group consisting of-N- and -O-, with the proviso that at least two of A, B and C are nitrogen atoms; G1 is selected from the group consisting of -CH2-, -NH- and -O-; G2 is selected from the group consisting of -NR4- and -O-; R1 represents: ➢ a 8 to 10 membered bicyclic N-containing heteroaryl group optionally substituted with a C1-4 carboxyalkyl group or a C1-4 aminoalkyl group, ➢ a pyridyl group optionally substituted with one or more substituents selected from hydroxy groups, C1-4 alkyl groups, C1-4 carboxyalkyl groups, C1-4 haloalkyl groups, C1-4 alkoxy groups, amino groups, C1-4 aminoalkyl groups and C1-4 aminoalkoxy groups, ➢ a pyridone group substituted with one or more C1-4 alkyl groups; C1-4 haloalkyl groups or C1-4 aminoalkyl groups, or ➢ a group of formula: wherein: • Ra represents a hydrogen atom, a halogen atom, a C1-4 alkyl group, C3-4 cycloalkyl group or a -CF3 group; • Rb represents a hydrogen atom, a halogen atom, a C14 alkyl group, a -CF3 group or a C1-4 alkoxy group; • Rd represents a hydrogen atom, a C1-4 alkyl group or a C1-4 alkoxy group; • Rc represents: ○ a hydrogen atom, a C1-4 hydroxyalkyl group, a C1-4 aminoalkyl group which is optionally substituted with one or more substituents selected from halogen atoms, hydroxy groups and -CF3 groups; ○ a 4 to 6-membered saturated N-containing heterocyclic ring optionally substituted with a C1-2 carboxyalkyl group; ○ -(CH2)(0-4)-C(O)OR', -(CH2)(0-4)-C(O)NR'R", -(CH2)(0-4)-NHC(O)R", -S(O)2NR'R", -O-(CH2)(2-4)NR'R", -O-(CH2)(1-4)C(O)OR", -O-(CH2)(1-4)-C(O)NR'R", -(CH2)(0-4)-NR'R", -(CH2)(0-4)-CONHS(O)2R', -(CH2)(0-4)-NHS(O)2R' or -(CH2)(0-3)-N H-(CH2)(1-3)-(NH)(0-1)S(O)2R' wherein, ■ R' represents a hydrogen atom or a C1-4 alkyl group, ■ R" represents a hydrogen atom, a C1-4 alkyl group, a C3-4 cycloalkyl group, a C1-4 carboxyalkyl group, a C1-4 haloalkyl group, a C1-4 hydroxyalkyl group or a 6 membered, saturated N-containing heterocyclic ring, or ■ R' and R" together with the nitrogen atom to which they are attached from a 4 to 6 membered heterocyclic group which contains, as heteroatoms, one N atom and, optionally, one further atom selected from N and O, and which is optionally substituted with a carboxy or a C1-4 carboxyalkyl group, or Rc together with Rd form a C5-6 cycloalkyl group optionally substituted by a -NHRf group, wherein Rf is selected from the group consisting of a hydrogen atom and a carboxymethyl group; R2 and R3 are independently selected from the group consisting of hydrogen atoms, halogen atoms and C1-4 alkyl groups; and R4 is selected from the group consisting of a hydrogen atom, a phenyl group, a C3-4 cycloalkyl-C1-4 alkyl group, C1-4 aminoalkyl group, C1-4 haloalkyl group and a linear or branched C1-4 alkyl group which is optionally substituted by a phenyl or a pyridyl group.

  通用公式（I）的新衍生物，或其药用可接受盐或N-氧化物，其中， A选自-N-，-O-和-S-组成的群; B和C分别选自-N-和-O-组成的群，但至少有两个A，B和C是氮原子; G1选自-CH2-，-NH-和-O-组成的群; G2选自-NR4-和-O-组成的群; R1代表: ➢一个含氮杂环的8到10成员双环基团，可选择地取代为C1-4羧基烷基基团或C1-4氨基烷基基团， ➢一个吡啶基，可选择地取代为一个或多个取代基，所选取代基包括羟基、C1-4烷基基团、C1-4羧基烷基基团、C1-4卤代烷基基团、C1-4烷氧基团、氨基、C1-4氨基烷基基团和C1-4氨氧基团， ➢一个吡啶酮基，取代为一个或多个C1-4烷基基团；C1-4卤代烷基基团或C1-4氨基烷基基团，或 ➢一个公式的基团： 其中: • Ra代表氢原子、卤原子、C1-4烷基基团、C3-4环烷基基团或-CF3基团; • Rb代表氢原子、卤原子、C14烷基基团、- 基团或C1-4烷氧基团; • Rd代表氢原子、C1-4烷基基团或C1-4烷氧基团; • Rc代表: ○氢原子、C1-4羟基烷基基团、C1-4氨基烷基基团，可选择地取代为一个或多个取代基，所选取代基包括卤原子、羟基和- 基团; ○一个4到6成员饱和的含氮杂环环，可选择地取代为C1-2羧基烷基基团; ○-( )(0-4)-C(O)OR'，-( )(0-4)-C(O)NR'R"，-( )(0-4)-NHC(O)R"，-S(O)2NR'R"，-O-( )(2-4)NR'R"，-O-( )(1-4)C(O)OR"，-O-( )(1-4)-C(O)NR'R"，-( )(0-4)-NR'R"，-( )(0-4)-CONHS(O)2R'，-( )(0-4)-NHS(O)2R'或-( )(0-3)-N H-( )(1-3)-(NH)(0-1)S(O)2R'其中， ■ R'代表氢原子或C1-4烷基基团， ■ R"代表氢原子、C1-4烷基基团、C3-4环烷基基团、C1-4羧基烷基基团、C1-4卤代烷基基团、C1-4羟基烷基基团或6成员饱和的含氮杂环环，或 ■ R'和R"与它们连接的氮原子一起形成一个4到6成员的杂环基团，该基团包含一个N原子和可选择地一个进一步选择自N和O的原子，并可选择地取代为羧基或C1-4羧基烷基基团， 或Rc与Rd一起形成一个可选择地由-NHRf基团取代的C5-6环烷基基团，其中Rf选自氢原子和羧甲基基团; R2和R3分别选自氢原子、卤原子和C1-4烷基基团;和 R4选自氢原子、苯基团、C3-4环烷基-C1-4烷基基团、C1-4氨基烷基基团、C1-4卤代烷基基团和可选择地由苯基或吡啶基取代的线性或支链C1-4烷基基团。
• Modular Generation of (Iodinated) Polyarenes Using Triethylgermane as Orthogonal Masking Group
  作者：Tatjana Kreisel、Marvin Mendel、Adele E. Queen、Kristina Deckers、Daniel Hupperich、Julian Riegger、Christoph Fricke、Franziska Schoenebeck

  DOI：10.1002/anie.202201475

  日期：2022.5.9

  A complementary modular coupling approach to the widely employed Suzuki coupling is disclosed herein, relying on organogermane-containing building blocks paired with air-stable PdI dimer based bond construction, which allows to significantly shorten the reaction times and close gaps in the accessible compound space.

  本文公开了一种与广泛采用的 Suzuki 偶联互补的模块化偶联方法，该方法依赖于含有有机锗烷的结构单元与基于空气稳定的 Pd 二聚体的键结构配对，这允许显着缩短反应时间并封闭可接近的化合物空间中的间隙。
• 1,2,4-OXADIAZOLE DERIVATIVES AND THEIR THERAPEUTIC USE
  申请人：Giulio Matassa Victor

  公开号：US20110311485A1

  公开（公告）日：2011-12-22

  The present disclosure relates to 1, 2, 4 oxadiazole derivatives of formula (I) as well as pharmaceutical compositions comprising them, and their use in therapy as agonists of the S1P1 receptors.

  本公开涉及公式（I）的1,2,4-噁二唑衍生物，以及包含它们的药物组合物，以及它们作为S1P1受体激动剂在治疗中的使用。