1-methoxy-1,3-bis(trimethylsilyloxy)dodeca-1,3-diene | 1031694-91-3

• 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: 1-methoxy-1,3-bis(trimethylsilyloxy)dodeca-1,3-diene
• 英文别名: 1-methoxy-1,3-bis(trimethylsilyloxy)-1,3-dodecadiene；(1-methoxy-3-trimethylsilyloxydodeca-1,3-dienoxy)-trimethylsilane
• CAS: 1031694-91-3
• 化学式: C₁₉H₄₀O₃Si₂
• 分子量: 372.696
• InChiKey: DMSUYSDVVRDYSM-UHFFFAOYSA-N

物化性质

• 沸点：
  376.4±32.0 °C(Predicted)
• 密度：
  0.888±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.81
• 重原子数：
  24.0
• 可旋转键数：
  13.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-methoxy-1,3-bis(trimethylsilyloxy)dodeca-1,3-diene 、 1,1-dichloro-4-ethoxy-but-3-en-2-one 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以45%的产率得到methyl 6-dichloromethyl-2-hydroxy-3-octylbenzoate
  参考文献：
  名称：

  Synthesis of 6-formylsalicylates based on regioselective [3+3] cyclocondensations of 1,3-bis(silyloxy)-1,3-butadienes with 1,1-dichloro-4-ethoxy-3-buten-2-ones

  摘要：

  6-Formylsalicylates are prepared by regioselective [3+3] cyclocondensations of L3-bis(silyloxy)-1,3-butadienes with 1,1-dichloro-4-ethoxy-3-buten-2-ones and subsequent transformation of the dichloromethyl into a formyl group. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.05.038

文献信息

• First synthesis of functionalized 5-aryl-3-(trifluoromethyl)phenols by regioselective [3+3] cyclocondensations of 1,3-bis(silyloxy)-1,3-butadienes with 3-aryl-3-silyloxy-1-trifluoromethyl-2-en-1-ones
  作者：Stefan Büttner、Abdolmajid Riahi、Ibrar Hussain、Mirza A. Yawer、Mathias Lubbe、Alexander Villinger、Helmut Reinke、Christine Fischer、Peter Langer

  DOI：10.1016/j.tet.2008.12.076

  日期：2009.3

  A variety of functionalized 5-aryl-3-(trifluoromethyl)phenols were prepared by the first TiCl4-mediated [3+3] cyclocondensation of 1,3-bis(trimethylsilyloxy)-1,3-butadienes with 3-aryl-3-trimethylsilyloxy-1-trifluoromethyl-2-en-1-ones.

  通过第一个TiCl 4介导的1,3-双（三甲基甲硅烷氧基）-1,3-丁二烯与3-芳基-3的[3 + 3]环缩合反应，制备了各种官能化的5-芳基-3-（三氟甲基）苯酚。-三甲基甲硅烷氧基-1-三氟甲基-2-烯-1-酮。
• Synthesis of Functionalized Biaryls Based on a Heck Cross-Coupling-[3+3] Cyclization Strategy
  作者：Peter Langer、Gerson Mroß、Helmut Reinke

  DOI：10.1055/s-2008-1072654

  日期：——

  6-Arylsalicylates were regioselectively prepared by formal [3+3] cyclization of 1,3-bis(silyloxy)-1,3-butadienes with 1-aryl-3-ethoxyprop-2-en-1-ones which are available by Heck reaction of benzoyl chlorides with ethylvinyl ether. In this context, the first [3+3] cyclizations of brominated substrates are reported.

  通过1,3-双(硅氧基)-1,3-丁二烯与1-芳基-3-乙氧基丙-2-烯-1-酮的正式[3+3]环化反应，区域选择性地合成了6-芳基水杨酸酯。而1-芳基-3-乙氧基丙-2-烯-1-酮则可通过苯甲酰氯与乙基乙烯基醚的Heck反应获得。在这样的背景下，首次报道了溴化底物的[3+3]环化反应。
• Synthesis of Functionalized Salicylates by Formal [3+3] Cyclocondensation of 1,3-Bis(silyloxy)buta-1,3-dienes with 3-Alkoxy-2-en-1-ones
  作者：Peter Langer、Gerson Mroß、Simone Ladzik、Helmut Reinke、Anke Spannenberg、Christine Fischer

  DOI：10.1055/s-0029-1216814

  日期：2009.7

  The formal [3+3] cyclization of 1,3-bis(silyloxy)buta-1,3-dienes with 1-aryl-3-ethoxyprop-2-en-1-ones, available by Heck reaction of benzoyl chlorides with ethyl vinyl ether, afforded a variety of 6-arylsalicylates. The reaction of the products with concentrated sulfuric acid resulted in the formation of fluorenones. 6-Alkylsalicylates were prepared by cyclization of 1,3-bis(silyl­oxy)buta-1,3-dienes

  1,3-双（甲硅烷氧基）丁1,3-二烯与1-芳基-3-乙氧基丙-2-烯-1-酮的正式[3 + 3]环化，可通过苯甲酰氯与乙基的Heck反应获得乙烯基醚，得到各种6-芳基水杨酸酯。产物与浓硫酸的反应导致芴酮的形成。通过将1，3-双（甲硅烷氧基）丁1，3-二烯与脂族烯酮环合制备6-烷基水杨酸酯。 芳烃-环化-钯-区域选择性-甲硅烷基烯醇醚
• Regioselective synthesis of 4-acyl-1-hydroxy-2,3-benzodioates by chelation-controlled [3+3] annulation of 3-acyl-4-ethoxy-2-oxo-3-enoates with 1,3-bis(trimethylsilyloxy)-1,3-butadienes
  作者：Abdolmajid Riahi、Mohanad Shkoor、Olumide Fatunsin、Rasheed Ahmad Khera、Christine Fischer、Peter Langer

  DOI：10.1039/b905556h

  日期：——

  4-Acyl-1-hydroxy-2,3-benzodioates were regioselectively prepared by chelation-controlled [3+3] cyclization of 1,3-bis(trimethylsilyloxy)-1,3-butadienes with 3-acyl-4-ethoxy-2-oxo-3-enoates.

  4-酰基-1-羟基-2,3-苯并二氧戊环-4-羧酸酯通过1,3-双(三甲基硅氧基)-1,3-丁二烯与3-酰基-4-乙氧基-2-氧代-3-烯酸酯的螯控[3+3]环化反应进行了区域选择性的制备。
• Regioselective [3+3] Cyclization of 1,3-Bis(silyloxy)buta-1,3-dienes with 1,1,1-Trifluoro-4-(silyloxy)alk-3-en-2-ones: New and Convenient Synthesis of Functionalized 5-Alkyl-3-(trifluoromethyl)phenols
  作者：Stefan Büttner、Alina Bunescu、Sebastian Reimann、T. H. Tam Dang、Thomas Pundt、Renske Klassen、Andreas Schmidt、Nazken K. Kelzhanova、Zharylkasyn A. Abilov、Tariel V. Ghochikyan、Ashot S. Saghiyan、Alexander Villinger、Helmut Reinke、Anke Spannenberg、Peter Langer

  DOI：10.1002/hlca.201200056

  日期：2013.1

  Functionalized 5‐alkyl‐3‐(trifluoromethyl)phenols were prepared by formal [3+3] cyclization of 1,3‐bis(silyloxy)buta‐1,3‐dienes with 1,1,1‐trifluoro‐4‐(silyloxy)alk‐3‐en‐2‐ones derived from 1,1,1‐trifluoroalkane‐2,4‐diones. The latter were prepared by condensation of the dianion of 1,1,1‐trifluoropentane‐2,4‐dione with alkyl halides.

  功能化的5-烷基-3-（三氟甲基）酚是通过将1,3-双（甲硅烷氧基）丁烯-1,3-二烯与1,1,1-三氟-4-（甲硅烷氧基）进行正式的[3 + 3]环化而制备的）由1,1,1-三氟烷烃-2,4-二酮衍生而来的alk-3-en-2-one。后者是通过1,1,1-三氟戊烷-2,4-二酮的二价阴离子与烷基卤的缩合制备的。