trimethyl(2-methylene-4-((trimethylsilyl)oxy)butyl)silane | 137578-98-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: trimethyl(2-methylene-4-((trimethylsilyl)oxy)butyl)silane
• 英文别名: trimethyl{2-[2-(trimethylsiloxy)ethyl]allyl}silane；trimethyl-(2-methylene-4-trimethylsilyloxybutyl)-silane；Trimethyl-(2-methylene-4-trimethylsilyloxybutyl)silane；trimethyl-(2-methylidene-4-trimethylsilyloxybutyl)silane
• CAS: 137578-98-4
• 化学式: C₁₁H₂₆OSi₂
• 分子量: 230.498
• InChiKey: PXDOKQHCKDIKQA-UHFFFAOYSA-N

物化性质

• 沸点：
  231.0±20.0 °C(Predicted)
• 密度：
  0.814±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.12
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  trimethyl(2-methylene-4-((trimethylsilyl)oxy)butyl)silane 在 三氟甲磺酸三甲基硅酯 、 碳酸氢钠 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.5h， 以63%的产率得到(6S,8S)-10-methyl-4-methylene-8-phenyl-1-oxa-7-thiaspiro[5.5]undec-10-ene
  参考文献：
  名称：

  Convergent One-Pot Oxidative [n+ 1] Approaches to Spiroacetal Synthesis

  摘要：

  Two one-pot oxidative annulative approaches to spiroacetal synthesis are described. One approach uses a Lewis acid mediated Ferrier reaction in the fragment-coupling stage followed by DDQ-promoted oxidative carbon-hydrogen bond cleavage and cyclization. An alternative approach employs a Heck reaction for fragment coupling followed by DDQ-mediated enone formation and cyclization. These strategies provide convergent routes to common subunits in natural products, medicinal agents, and chemical libraries under mild reaction conditions.

  DOI：

  10.1021/acs.orglett.5b01736
• 作为产物：
  描述：

  3-甲基-3-丁烯-1-醇 、 三甲基氯硅烷 在 正丁基锂 、 四甲基乙二胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 48.25h， 以52%的产率得到trimethyl(2-methylene-4-((trimethylsilyl)oxy)butyl)silane
  参考文献：
  名称：

  超声促进异戊烯基乙醇双阴离子的形成：全氢呋喃[2,3-b]呋喃的直接合成

  摘要：

  已经发现，通过在乙醚-四氢呋喃中用丁基锂金属化，超声波可以加速异戊烯基醇二价阴离子的形成。该二价阴离子与羰基化合物反应，然后在Wacker型条件下进行分子内缩醛化反应，为合成2-取代的全氢呋喃[2,3- b ]呋喃提供了直接途径。 金属化-超声波-聚阴离子-Wacker型反应-环化-过氢呋喃[2,3- b ]呋喃

  DOI：

  10.1055/s-0030-1258168

文献信息

• [EN] NOVEL SPIROHETEROCYCLIC COMPOUNDS AS MGLU5 ANTAGONISTS<br/>[FR] NOUVEAUX COMPOSÉS SPIROHÉTÉROCYCLIQUES EN TANT QU'ANTAGONISTES DE MGLU5
  申请人：RECORDATI IRELAND LTD

  公开号：WO2012004400A1

  公开（公告）日：2012-01-12

  The invention provides compounds having the general formula (I) wherein X is O or S; R1 is C, N, O or S; R1a is CH, CH2, N or NH; R2 is a bond, CH or CH2; m is 1, 2 or 3; n is 1 or 2; when n is 2 or m is 2 or 3, the ring containing R1 may be fused with a benzene ring; each --- represents a single or double bond provided that one double bond extends from the carbon atom to which R3-C≡C- is bonded and that no ring carbon atom bears two double bonds; and R3, R4 and R5 represent a wide range of substituents. These compounds are selective for the metabotropic mGlu5 receptor. They, their solvates, hydrates, enantiomers, diastereomers, N-oxides and pharmaceutically acceptable salts, and pharmaceutical compositions containing them, can be used to treat diseases or disorders of the lower urinary tract, especially neuromuscular dysfunctions of the lower urinary tract. They may also be useful for the treatment of migraine; for the treatment of gastroesophageal reflux disease (GERD); for the treatment of anxiety disorder; for the treatment of abuse, substance dependence and substance withdrawal disorder; for the treatment of neuropathic pain disorder; and for the treatment of fragile X syndrome disorders.

  该发明提供了具有一般式（I）的化合物，其中X为O或S；R1为C、N、O或S；R1a为CH、CH2、N或NH；R2为键、CH或CH2；m为1、2或3；n为1或2；当n为2或m为2或3时，含有R1的环可能与苯环融合；每个---代表单键或双键，其中一个双键延伸自R3-C≡C-键合的碳原子，且没有环碳原子带有两个双键；R3、R4和R5代表各种取代基。这些化合物对代谢型mGlu5受体具有选择性。它们及其溶剂合物、水合物、对映体、非对映体异构体、N-氧化物和药学上可接受的盐，以及含有它们的药物组合物，可用于治疗下尿路的疾病或紊乱，特别是下尿路的神经肌肉功能紊乱。它们也可能对治疗偏头痛；治疗胃食管反流病（GERD）；治疗焦虑症；治疗滥用、物质依赖和物质戒断紊乱；治疗神经病性疼痛紊乱；以及治疗脆性X综合症紊乱有用。
• Tin(II) Trifluoromethanesulfonate-Catalyzed Highly Selective Synthesis of 2-Substituted 4-Methylenetetrahydropyrans from Trimethyl{2-[2-(trimethylsiloxy)ethyl]allyl}silane and Acetals
  作者：Takeshi Oriyama、Akihiro Ishiwata、Takeshi Suzuki

  DOI：10.1246/bcsj.74.569

  日期：2001.3

  A variety of 2-substituted 4-methylenetetrahydropyrans are easily produced by the reaction of acetals with trimethyl2-[2-(trimethylsiloxy)ethyl]allyl}silane under the influence of a catalytic amount of tin(II) trifluoromethanesulfonate.

  通过锡(II)三氟甲磺酸催化剂的作用，乙缩醛与三甲基2-[2-(三甲基硅氧基)乙基]烯丙基}硅烷反应，可以轻松制备多种2-取代的4-亚甲基四氢吡喃。
• Ultrasound-Promoted Formation of Isopentenyl Alcohol Dianion: Straightforward Synthesis of Perhydrofuro[2,3-b]furans
  作者：Francisco Alonso、Miguel Yus、Mamen Rodríguez-Fernández、Daniel Sánchez

  DOI：10.1055/s-0030-1258168

  日期：2010.9

  butyllithium in diethyl ether-tetrahydrofuran. The reaction of this dianion with carbonyl compounds followed by intramolecular acetalization under Wacker-type conditions provides a direct route for the synthesis of 2-substituted perhydrofuro[2,3-b]furans. metalation - ultrasound - polyanions - Wacker-type reaction - cyclization - perhydrofuro[2,3-b]furans

  已经发现，通过在乙醚-四氢呋喃中用丁基锂金属化，超声波可以加速异戊烯基醇二价阴离子的形成。该二价阴离子与羰基化合物反应，然后在Wacker型条件下进行分子内缩醛化反应，为合成2-取代的全氢呋喃[2,3- b ]呋喃提供了直接途径。 金属化-超声波-聚阴离子-Wacker型反应-环化-过氢呋喃[2,3- b ]呋喃
• Regiocontrol in the intramolecular silyl modified sakurai (ISMS) reaction. An efficient synthesis of a Dacus oleae fruit fly pheromone.
  作者：István E. Markó、Abdelaziz Mekhalfia

  DOI：10.1016/s0040-4039(00)91736-2

  日期：1992.3

  The ISMS reaction, which initially afforded a mixture of regioisomeric olefins, can now be controlled to produce only the exocyclic alkene. The ISMS methodology was used in a highly efficient synthesis of a Dacus oleae pheromone 8.

  最初提供区域异构烯烃混合物的ISMS反应现在可以进行控制，以仅生产环外烯烃。ISMS方法学被用于油茶信息素8的高效合成。
• NOVEL SPIROHETEROCYCLIC COMPOUNDS AS MGLU5 ANTAGONISTS
  申请人：Leonardi Amedeo

  公开号：US20120059015A1

  公开（公告）日：2012-03-08

  The invention is directed to methods of using antagonists selective for the metabotropic mGlu5 receptor to treat conditions of neuromuscular dysfunction of the lower urinary tract in a mammal. Provided are methods of treating a mammal suffering from a condition of neuromuscular dysfunction of the lower urinary tract by administering a selective mGlu5 antagonist. The selective mGlu5 antagonist may be administered alone or in combination with one or more additional therapeutic agents for treating such a condition. Also provided are methods of identifying selective mGlu5 antagonists that are useful for treating neuromuscular dysfunction of the lower urinary tract in a mammal. Methods for treating migraine and gastroesophageal reflux disease (GERD) using selective mGlu5 antagonists are also disclosed.

  本发明涉及使用选择性拮抗剂对代谢型mGlu5受体的方法，以治疗哺乳动物下尿道神经肌肉功能障碍的病症。提供了通过给予选择性mGlu5拮抗剂治疗患有下尿道神经肌肉功能障碍的哺乳动物的方法。该选择性mGlu5拮抗剂可以单独或与一种或多种其他治疗剂合并使用以治疗此类病症。还提供了用于治疗偏头痛和胃食管反流病（GERD）的选择性mGlu5拮抗剂的方法。同时还公开了用于鉴定对治疗哺乳动物下尿道神经肌肉功能障碍有用的选择性mGlu5拮抗剂的方法。