3-(4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷-2-基)噻吩-2-甲腈 | 942070-34-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 中文名称: 3-(4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷-2-基)噻吩-2-甲腈
• 英文名称: 3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-thiophene-2-carbonitrile
• 英文别名: 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-YL)thiophene-2-carbonitrile
• CAS: 942070-34-0
• 化学式: C₁₁H₁₄BNO₂S
• mdl: MFCD12405473
• 分子量: 235.115
• InChiKey: HUZWPBPPEDMPTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.54
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.545
• 拓扑面积：
  70.5
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  3-(4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷-2-基)噻吩-2-甲腈 、 6-[(6-chloropyridin-3-yl)methyl]-5-methyl-[1,2,5]oxadiazolo[3,4-b]pyridin-7-amine 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 0.5h， 以31 mg的产率得到3-[5-(7-amino-5-methyl-[1,2,5]oxadiazolo[3,4-b]pyridin-6-ylmethyl)pyridin-2-yl]thiophene-2-carbonitrile
  参考文献：
  名称：

  [EN] BENZYL-, (PYRIDIN-3-YL)METHYL- OR (PYRIDIN-4-YL)METHYL-SUBSTITUTED OXADIAZOLOPYRIDINE DERIVATIVES AS GHRELIN O-ACYL TRANSFERASE (GOAT) INHIBITORS
  [FR] DÉRIVÉS D'OXADIAZOLOPYRIDINE À SUBSTITUTION BENZYLE, (PYRIDIN-3-YL)MÉTHYLE OU (PYRIDIN-4-YL)MÉTHYLE UTILISÉS EN TANT QU'INHIBITEURS DE LA GHRÉLINE O-ACYLTRANSFÉRASE (GOAT)

  摘要：

  本发明涉及一般式（I）的化合物，其中基团R1和R2的定义如权利要求1中所述，该化合物具有有价值的药理特性，特别是与胃饥饿素O-酰基转移酶（GOAT）结合并调节其活性。这些化合物适用于治疗和预防可以受到该受体影响的疾病，如代谢性疾病，特别是肥胖症。

  公开号：

  WO2019149657A1
• 作为产物：
  描述：

  2-氰基噻吩 在 甲醇 、 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 、 4,4'-二叔丁基-2,2'-二吡啶 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 9.5h， 生成 3-(4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷-2-基)噻吩-2-甲腈
  参考文献：
  名称：

  Harnessing C–H Borylation/Deborylation for Selective Deuteration, Synthesis of Boronate Esters, and Late Stage Functionalization

  摘要：

  Ir-catalyzed deborylation can be used to selectively deuterate aromatic and heteroaromatic substrates. Combined with the selectivities of Ir-catalyzed C-H borylations, uniquely labeled compounds can be prepared. In addition, diborylation/deborylation reactions provide monoborylated regioisomers that complement those prepared by C-H borylation. Comparisons between Ir-catalyzed deborylations and Pd-catalyzed deborylations of diborylated indoles described by Movassaghi are made. The Ir-catalyzed process is more effective for deborylating aromatics and is generally more effective in the monodeborylation of diborylated thiophenes. These processes can be applied to complex molecules such as dopidogrel.

  DOI：

  10.1021/acs.joc.5b01588

文献信息

• Imidazo-pyrimidine derivatives as ligands for gaba receptors
  申请人：——

  公开号：US20020193385A1

  公开（公告）日：2002-12-19

  A class of 3-phenylimidazo[1,2-&agr;]pyrimidine derivatives, substituted at the meta position of the phenyl ring by an optionally substituted aryl or heteroaryl group which is directly attached or bridged by an oxygen atom or a —NH— linkage, and further substituted on the phenyl ring by alkyl, trifluoromethyl, alkoxy or one or two halogen atoms, especially fluoro, are selective ligands for GABA A receptors, in particular having good affinity for the &agr;2 and/or &agr;3 and/or &agr;5 subunit thereof, and are accordingly of benefit in the treatment and/or prevention of adverse conditions of the central nervous system, including anxiety, convulsions and cognitive disorders.

  一类3-苯基咪唑[1,2-&agr;]嘧啶衍生物，苯环的间位被取代，取代基可以是直接连接或通过氧原子或-NH-键桥接的取代芳基或杂环芳基，苯环上进一步被取代为烷基，三氟甲基，烷氧基或一个或两个卤素原子，特别是氟，是GABAA受体的选择性配体，特别是对其中的&agr;2和/或&agr;3和/或&agr;5亚基具有良好的亲和力，因此对于治疗和/或预防中枢神经系统的不良症状，包括焦虑，惊厥和认知障碍具有益处。
• WO2020002611A5
  申请人：——

  公开号：WO2020002611A5

  公开（公告）日：2022-06-16
• [EN] BENZYL-, (PYRIDIN-3-YL)METHYL- OR (PYRIDIN-4-YL)METHYL-SUBSTITUTED OXADIAZOLOPYRIDINE DERIVATIVES AS GHRELIN O-ACYL TRANSFERASE (GOAT) INHIBITORS<br/>[FR] DÉRIVÉS D'OXADIAZOLOPYRIDINE À SUBSTITUTION BENZYLE, (PYRIDIN-3-YL)MÉTHYLE OU (PYRIDIN-4-YL)MÉTHYLE UTILISÉS EN TANT QU'INHIBITEURS DE LA GHRÉLINE O-ACYLTRANSFÉRASE (GOAT)
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2019149657A1

  公开（公告）日：2019-08-08

  The present invention relates to compounds of general formula (I), wherein the groups R1 and R2 are defined as in claim 1, which have valuable pharmacological properties, in particular bind to ghrelin O-acyl transferase (GOAT) and modulate its activity. The compounds are suitable for treatment and prevention of diseases which can be influenced by this receptor, such as metabolic diseases, in particular obesity.

  本发明涉及一般式（I）的化合物，其中基团R1和R2的定义如权利要求1中所述，该化合物具有有价值的药理特性，特别是与胃饥饿素O-酰基转移酶（GOAT）结合并调节其活性。这些化合物适用于治疗和预防可以受到该受体影响的疾病，如代谢性疾病，特别是肥胖症。
• Harnessing C–H Borylation/Deborylation for Selective Deuteration, Synthesis of Boronate Esters, and Late Stage Functionalization
  作者：Venkata A Kallepalli、Kristin A. Gore、Feng Shi、Luis Sanchez、Ghayoor A. Chotana、Susanne L. Miller、Robert E. Maleczka、Milton R. Smith

  DOI：10.1021/acs.joc.5b01588

  日期：2015.8.21

  Ir-catalyzed deborylation can be used to selectively deuterate aromatic and heteroaromatic substrates. Combined with the selectivities of Ir-catalyzed C-H borylations, uniquely labeled compounds can be prepared. In addition, diborylation/deborylation reactions provide monoborylated regioisomers that complement those prepared by C-H borylation. Comparisons between Ir-catalyzed deborylations and Pd-catalyzed deborylations of diborylated indoles described by Movassaghi are made. The Ir-catalyzed process is more effective for deborylating aromatics and is generally more effective in the monodeborylation of diborylated thiophenes. These processes can be applied to complex molecules such as dopidogrel.