1-trimethylsilyloxy-3H-indene | 31928-64-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: 1-trimethylsilyloxy-3H-indene
• 英文别名: ((1H-inden-3-yl)oxy)trimethylsilane；3-((Trimethylsilyl)oxy)indene；3H-inden-1-yloxy(trimethyl)silane
• CAS: 31928-64-0
• 化学式: C₁₂H₁₆OSi
• 分子量: 204.344
• InChiKey: YXZRFWIVBXHTBE-UHFFFAOYSA-N

物化性质

• 沸点：
  244.4±9.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.44
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  1-trimethylsilyloxy-3H-indene 在 四氯化钛 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 4.0h， 生成 2-(propan-2-ylidene)-2,3-dihydro-1H-inden-1-one
  参考文献：
  名称：

  Mitra, R. B.; Muljiani, Z.; Reddy, G. B., Synthetic Communications, 1986, vol. 16, # 9, p. 1099 - 1108

  摘要：

  DOI：
• 作为产物：
  描述：

  1-茚酮 在 正丁基锂 、 三甲基氯硅烷 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二异丙胺 为溶剂， 以82.5%的产率得到1-trimethylsilyloxy-3H-indene
  参考文献：
  名称：

  CATALYST FOR POLYOLEFIN PRODUCTION AND PROCESS FOR PRODUCING POLYOLEFIN

  摘要：

  公开号：

  EP0834519B1

文献信息

• Divergent Iron-Catalyzed Coupling of<i>O</i>-Acyloximes with Silyl Enol Ethers
  作者：Hai-Bin Yang、Nicklas Selander

  DOI：10.1002/chem.201605636

  日期：2017.2.3

  An iron‐catalyzed coupling reaction of O‐acyloximes and O‐benzoyl amidoximes with silyl enol ethers is reported. The protocol provides access to functionalized pyrroles, 1,6‐ketonitriles, pyrrolines and imidazolines via carbon‐centered radicals generated from an initially formed iminyl radical. The intramolecular cyclization and ring‐opening processes of the iminyl radical take place preferentially

  据报道，O-酰基肟和O-苯甲酰a肟与甲硅烷基烯醇醚的铁催化偶联反应。该协议提供了通过最初形成的亚胺基生成的碳中心基团来访问官能化的吡咯，1,6-酮腈，吡咯啉和咪唑啉的途径。亚胺基的分子内环化和开环过程优先于通过1,3-氢转移进行的反应，从而提供了对肟催化的铁催化反应的见解。廉价且环保的铁催化剂，广泛的底物范围和官能团的相容性使该方案可用于合成有价值的含氮产物。
• Synthesis of 3-Fluoropyridines via Photoredox-Mediated Coupling of α,α-Difluoro-β-iodoketones with Silyl Enol Ethers
  作者：Sofya I. Scherbinina、Oleg V. Fedorov、Vitalij V. Levin、Vladimir A. Kokorekin、Marina I. Struchkova、Alexander D. Dilman

  DOI：10.1021/acs.joc.7b02467

  日期：2017.12.15

  A method for the synthesis of diversely substituted 3-fluoropyridines from two ketone components is described. The reaction involves photoredox coupling of α,α-difluoro-β-iodoketones with silyl enol ethers catalyzed by fac-Ir(ppy)3 under blue LED irradiation with subsequent one-pot condensation with ammonium acetate. Based on cyclic voltammetry studies, it was determined that α,α-difluoro-β-iodoketones

  描述了一种由两种酮组分合成不同取代的3-氟吡啶的方法。该反应涉及在蓝色LED照射下，fac -Ir（ppy）3催化α，α-二氟-β-碘酮与甲硅烷基烯醇醚的光氧化还原偶联，随后与乙酸铵进行一锅缩合。根据循环伏安法研究，确定与2,2,2-三氟-1-碘乙烷相比，α，α-二氟-β-碘酮的还原明显容易，这可能归因于羰基的影响。
• Photoredox-Catalyzed Generation of Sulfamyl Radicals: Sulfonamidation of Enol Silyl Ether with Chlorosulfonamide
  作者：Qiyu Luo、Runyu Mao、Yan Zhu、Yonghui Wang

  DOI：10.1021/acs.joc.9b02062

  日期：2019.11.1

  A novel and practical photoredox-catalyzed generation of sulfamyl radicals followed by radical sulfonamidation of enol silyl ether has been described. Diverse functionalized β-ketosulfonamides were prepared in modest to excellent yields under mild and economic reaction conditions through the present catalytic protocol. Furthermore, the methodology developed provides an efficient and convenient approach

  已经描述了新颖且实用的光氧化还原催化的磺酰胺基的产生，随后是烯醇甲硅烷基醚的自由基磺酰胺化。通过本发明的催化方案，在温和且经济的反应条件下以适度至优异的产率制备了多种官能化的β-酮磺酰胺。此外，开发的方法为合成抗癫痫药Zonisamide提供了一种有效而便捷的方法。
• Dioxopyrrolines. LIII. Stereochemical Pathway of (2+2) Photocycloaddition Reaction of 4-Ethoxycarbonyl-5-phenyl-1H-pyrrole-2,3-dione to Cyclic Enol Trimethylsilyl Ethers.
  作者：Takehiko SANO、Miyuki HIROSE、Yoshie HORIGUCHI、Fumiyuki KIUCHI、Yoshisuke TSUDA

  DOI：10.1248/cpb.41.64

  日期：——

  The photocycloaddition reaction of the dioxopyrroline 1 to cyclic trimethylsilyloxy olefins was examined. The addition of 3-trimethylsilyloxy-1H-indene and 4-trimethylsilyloxy-1, 2-dihydronaphthalene occurred in a regio- and stereoselective manner to give the cis-anti-cis cyclobutanes 3 and 4, respectively. The stereochemical result supported the stereo-selection rule which states that the photocycloaddition of a very polar dioxopyrroline-olefin pair proceeds in an s+s manner via f favored O-endo-π-complex transition. On the other hand, the addition of 1-trimethylsilyloxy-cyclopentene and 1-trimethylsilyloxycyclohexene occurred less stereoselectively, proceeding predominantly in an s+a manner to give the adducts 5a, b, 6a, b, 7a, b, and 12. The results are consistent with the prediction of the stereo-selection rule obtained by assuming that these dioxopyrroline-olefin pairs are polar. The latter cases demonstrate that an incresed steric hindrance around the olefin moiety affects the polarity of enone-olefin pair in the transition state.

  研究了二氧吡咯啉1与环状三甲基硅氧基烯烃的光环加成反应。3-三甲基硅氧基-1H-茚和4-三甲基硅氧基-1,2-二氢萘进行了区域选择性和立体选择性的加成反应，分别得到顺反顺式环丁烷3和4。立体化学结果支持立体选择规则，该规则指出非常极性的二氧吡咯啉-烯烃对的光环加成反应通过优先的O-endo-π-复合物过渡态以s+s方式进行。另一方面，1-三甲基硅氧基环戊烯和1-三甲基硅氧基环己烯的加成立体选择性较低，主要以s+a方式进行，得到加合物5a, b, 6a, b, 7a, b和12。结果与假设这些二氧吡咯啉-烯烃对为极性时得到的立体选择规则预测一致。后一种情况表明，烯烃部分周围的立体阻碍增加会影响过渡态中烯酮-烯烃对的极性。
• REACTIONS OF PERFLUOROALKANE-SULFONYL CHLORIDES WITH SILYL ENOL ETHERS CATALYZED BY A RUTHENIUM(II) PHOSPHINE COMPLEX
  作者：Nobumasa Kamigata、Kumiko Udodaira、Toshio Shimizu

  DOI：10.1080/10426509708031590

  日期：1997.10.1

  Abstract Reactions of trifluoromethane- and tridecafluorohexanesulfonyl chlorides with silyl enol ethers have been investigated in the presence of a ruthenium(II) phosphine complex. Perfluoroalkylation and chlorination occurred depending on the substituent of silyl enol ether; i.e. perfluoroalkylated compound was selectively obtained in the reactions with silyl enol ether possessing an electron-withdrawing

  摘要 在钌 (II) 膦配合物存在下，研究了三氟甲烷和十三氟己烷磺酰氯与甲硅烷基烯醇醚的反应。全氟烷基化和氯化反应的发生取决于甲硅烷基烯醇醚的取代基；即与具有吸电子基团的甲硅烷基烯醇醚反应选择性地得到全氟烷基化化合物，而与具有给电子基团的甲硅烷基烯醇醚反应选择性地生成氯化物。