(Z)-1,2-bis(trimethylsiloxy)ethylene | 26327-98-0

• 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: (Z)-1,2-bis(trimethylsiloxy)ethylene
• 英文别名: (Z)-2,2,7,7-tetramethyl-3,6-dioxa-2,7-disilaoct-4-ene；(Z)-Bis-1,2-(trimethylsilyloxy)ethylene；trimethyl-[(Z)-2-trimethylsilyloxyethenoxy]silane
• CAS: 26327-98-0
• 化学式: C₈H₂₀O₂Si₂
• 分子量: 204.417
• InChiKey: DSNMSIRQEQAGHB-FPLPWBNLSA-N

物化性质

• 沸点：
  172.6±13.0 °C(Predicted)
• 密度：
  0.857±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.16
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-1,2-bis(trimethylsiloxy)ethylene 在 苯乙酮 作用下， 以 乙醚 为溶剂， 生成 E-2,3-bis(trimethylsiloxy)-2-butene
  参考文献：
  名称：

  2.2-Dimethyl-1.3-dioxol und Z-Bis-trimethylsiloxy-äthylen als cyclophile mit nucleophilem charakter bei photochemischen (2+2) und thermischen (4+2)-cycloadditionen

  摘要：

  DOI：

  10.1016/s0040-4039(00)71344-x
• 作为产物：
  描述：

  在 H₂ 作用下， 以 氘代四氢呋喃 为溶剂， 以41%的产率得到(Z)-1,2-bis(trimethylsiloxy)ethylene
  参考文献：
  名称：

  Protasiewicz, John D.; Lippard, Stephen J., Journal of the American Chemical Society, 1991, vol. 113, # 18, p. 6564 - 6570

  摘要：

  DOI：

文献信息

• A novel synthetic approach toward the zaragozic acids core structure
  作者：Hiroo Koyama、Richard G. Ball、Gregory D. Berger

  DOI：10.1016/0040-4039(94)88460-9

  日期：1994.12

  A novel synthetic approach toward the zaragozic acids core structure is described. New dipolarophiles in the 1,3-dipolar cycloaddition to the carbonyl ylides are reported. The substituent effect of the dipolarophiles is also discussed.

  描述了一种新颖的合成方法，用于合成马来果酸的核心结构。据报道，在1，3-偶极环加成羰基上有新的偶极亲和性。还讨论了双亲亲油的取代基作用。
• Formation of Enamines via Catalytic Dehydrogenation by Pincer-Iridium Complexes
  作者：Yansong J. Lu、Xiawei Zhang、Santanu Malakar、Karsten Krogh-Jespersen、Faraj Hasanayn、Alan S. Goldman

  DOI：10.1021/acs.joc.9b02846

  日期：2020.3.6

  lesser crowding of the di-isopropylphosphino-substituted catalysts. Experimentally determined kinetic isotope effects in conjunction with DFT-based analysis support a dehydrogenation mechanism involving initial pre-equilibrium oxidative addition of the amine α-C-H bond followed by rate-determining elimination of the β-C-H bond.

  发现二异丙基膦基取代的夹钳连接的铱催化剂对于简单叔胺的脱氢以产生烯胺比先前报道的二叔丁基膦基取代的物种明显更有效。还发现，二异丙基膦基取代的配合物催化几种β-官能化叔胺的脱氢反应，得到相应的1，2-二官能化烯烃。二叔丁基膦基取代的物质对这种底物无效；据推测，明显的差异归因于二异丙基膦基取代的催化剂较少的拥挤。
• Efficient synthesis of trifluoromethyl-substituted 5,6-dihydro-4H-1,2-oxazines by the hetero-Diels-Alder reaction of 1,1,1-trifluoro-2-nitroso-2-propene and electron-rich olefins
  作者：Reinhold Zimmer、Hans Ulrich Reissig

  DOI：10.1021/jo00027a058

  日期：1992.1

  1,1,1-Trifluoro-2-nitroso-2-propene (1) was generated in situ by treatment of the alpha-bromo oxime 5 with base. Moderate to excellent yields of the 3-trifluoromethyl-substituted 1,2-oxazines 17-27 were obtained from the reaction of 1 and the silyl enol ethers 6-16, respectively. Other dienophiles, i.e., allyltrimethylsilane, cyclopentadiene, furan, and dihydropyran, upon reaction with 1 provided the cycloadducts 31-34, respectively, in good yield. The results demonstrated that 1 is probably the most reactive heterodiene that has so far been employed in this type of Diels-Alder reaction (i.e., Diels-Alder reaction with inverse electron demand). The mechanism of the reaction and diastereoselectivity of the cycloadditions are discussed. The reaction of 1 with indole and acetyl acetone afforded the oxime 38 and a mixture of the isomers 40-42, respectively. Also, ring openings and other transformations of the trifluoromethyl-substituted 1,2-oxazines were effected. Acid-induced desilylation of the silylated 1,2-oxazines provided oximes like 46 and 48 or 6-hydroxy-1,2-oxazines like 47. Treatment of the 1,2-oxazines with Mo(CO)6 in the presence of trifluoroacetic acid produced 2-trifluoromethyl-substituted pyrroles (e.g., 18 --> 50). The reduction of the 1,2-oxazines afforded either gamma-hydroxy oximes (e.g., 19 --> 51) or amino alcohols (e.g., 32 --> 52, 31 --> 55). The reduction of the indole derivative 38 by LiAlH4 provided the trifluoromethyl-substituted tryptamine 56. The results of these explorative studies demonstrated that readily available trifluoromethyl-substituted 1,2-oxazines could be efficiently converted into other compounds that bear a trifluoromethyl group.
• Reissig, Hans-Ulrich; Hippeli, Claudia; Arnold, Thomas, Chemische Berichte, 1990, vol. 123, # 12, p. 2403 - 2411
  作者：Reissig, Hans-Ulrich、Hippeli, Claudia、Arnold, Thomas

  DOI：——

  日期：——
• Baudrillard, Vincent; Ple, Gerard; Davoust, Daniel, Journal of Chemical Research, Miniprint, 1997, # 12, p. 2820 - 2831
  作者：Baudrillard, Vincent、Ple, Gerard、Davoust, Daniel、Duhamel, Lucette

  DOI：——

  日期：——