[(Z)-1,2-Bis-(tert-butyl-dimethyl-silanyloxy)-vinyloxy]-benzene | 150811-71-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(Z)-1,2-Bis-(tert-butyl-dimethyl-silanyloxy)-vinyloxy]-benzene
• 英文别名: tert-butyl-[(Z)-2-[tert-butyl(dimethyl)silyl]oxy-1-phenoxyethenoxy]-dimethylsilane
• CAS: 150811-71-5
• 化学式: C₂₀H₃₆O₃Si₂
• 分子量: 380.675
• InChiKey: VRWMISOCNYLFGM-VLGSPTGOSA-N

物化性质

• 沸点：
  371.7±32.0 °C(predicted)
• 密度：
  0.938±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.91
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  苯甲醛 、 [(Z)-1,2-Bis-(tert-butyl-dimethyl-silanyloxy)-vinyloxy]-benzene 在 tin(II) trifluoromethanesulfonate 、 二乙酸二丁基锡 、 (S)-(-)-1-甲基-2-(1-哌啶基甲基)吡咯烷 作用下， 以 二氯甲烷 为溶剂， 生成 (2S,3R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-3-phenyl-propionic acid phenyl ester 、 (2S,3S)-2-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-3-phenyl-propionic acid phenyl ester 、 (2R,3R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-3-phenyl-propionic acid phenyl ester 、 (2R,3S)-2-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-3-phenyl-propionic acid phenyl ester
  参考文献：
  名称：

  反选择性不对称羟醛反应。抗-αβ-二羟基苯基酯衍生物的对映选择性合成

  摘要：

  在手性锡（II）路易斯酸的存在下，衍生自（E）-苯基α-叔丁基二甲基甲硅烷氧基乙酸酯的甲硅烷基烯醇醚与醛反应，得到相应的抗-醛醇加合物，抗-α，β-二羟基酯衍生物，具有高的非对映选择性和对映选择性。

  DOI：

  10.1016/s0040-4039(00)76899-7
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 、 phenyl (tert-butyldimethylsilyloxy)acetate 在 正丁基锂 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 正己烷 为溶剂， 生成 [(Z)-1,2-Bis-(tert-butyl-dimethyl-silanyloxy)-vinyloxy]-benzene
  参考文献：
  名称：

  Highly selective generation and application of (E)- and (Z)-silyl ketene acetals from .alpha.-hydroxy esters

  摘要：

  A method for the stereoselective synthesis of silyl ketene acetals from a-hydroxy esters is described. Internal quench with excess TMSCI of the lithium enolate at -100-degrees-C, which is generated using a hindered base, LTMP, leads to the selective formation of (E)-silyl ketene acetal. In contrast, the deprotonation at -100-degrees-C using LHMDS in THF-HMPA (4:1), followed by treatment with tert-butyldimethylsilyl chloride affords the (Z)-silyl ketene acetal selectively. The method can be applied to the stereoselective reaction of the Ireland ester enolate Claisen rearrangement and aldol synthesis.

  DOI：

  10.1021/jo00072a005

文献信息

• Highly selective enolization method for heteroatom substituted esters; its application to the ireland ester enolate claisen rearrangement
  作者：Kouji Hattori、Hisashi Yamamoto

  DOI：10.1016/s0040-4020(01)81109-1

  日期：1994.3

  A method for the stereoselective synthesis of silyl ketene acetals from α-siloxy esters, β-hydroxy esters, and α-amino esters is described. Internal quench with excess trimethylsilyl chloride of the lithium enolate at −100 °C, which is generated using a hindered base, LTMP, leads to the selective formation of E-silyl ketene acetal. In contrast, the deprotonation at −100 °C using LHMDS in THF-HMPA (4:1)

  描述了一种由α-甲硅烷氧基酯，β-羟基酯和α-氨基酯立体选择性合成甲硅烷基烯酮缩醛的方法。使用受阻碱LTMP在-100°C下用过量的烯醇锂的三甲基甲硅烷基氯进行内部淬灭，可选择性地形成E-甲硅烷基乙烯酮缩醛。相反，使用LHMDS在THF-HMPA（4：1）中在-100°C进行去质子化，然后用叔丁基二甲基甲硅烷基氯进行处理，可以选择性地得到Z-甲硅烷基烯酮缩醛。该方法可用于爱尔兰酯烯酸酯克莱森重排的立体选择反应。
• Hattori Kouji, Yamamoto Hisashi, Tetrahedron, 50 (1994) N 10, S 3099-3112
  作者：Hattori Kouji, Yamamoto Hisashi

  DOI：——

  日期：——
• Highly selective generation and application of (E)- and (Z)-silyl ketene acetals from .alpha.-hydroxy esters
  作者：Kouji Hattori、Hisashi Yamamoto

  DOI：10.1021/jo00072a005

  日期：1993.9

  A method for the stereoselective synthesis of silyl ketene acetals from a-hydroxy esters is described. Internal quench with excess TMSCI of the lithium enolate at -100-degrees-C, which is generated using a hindered base, LTMP, leads to the selective formation of (E)-silyl ketene acetal. In contrast, the deprotonation at -100-degrees-C using LHMDS in THF-HMPA (4:1), followed by treatment with tert-butyldimethylsilyl chloride affords the (Z)-silyl ketene acetal selectively. The method can be applied to the stereoselective reaction of the Ireland ester enolate Claisen rearrangement and aldol synthesis.
• Anti-selective asymmetric aldol reactions. Enantioselective synthesis of anti-αβ-dihydroxy phenyl ester derivatives
  作者：Shū Kobayashi、Takashi Kawasuji

  DOI：10.1016/s0040-4039(00)76899-7

  日期：1994.5

  of a chiral tin(II) Lewis acid, the silyl enol ether derived from (E)-phenyl α-t-butyldimethylsiloxyacetate reacted with aldehydes to afford the corresponding anti-aldol adducts, anti-α,β-dihydroxy ester derivatives, in high yields with high diastereo- and enantioselectivities.

  在手性锡（II）路易斯酸的存在下，衍生自（E）-苯基α-叔丁基二甲基甲硅烷氧基乙酸酯的甲硅烷基烯醇醚与醛反应，得到相应的抗-醛醇加合物，抗-α，β-二羟基酯衍生物，具有高的非对映选择性和对映选择性。