trimethyl((1E,3E)-3-methyl-4-phenylbuta-1,3-dienyl)silane | 116973-01-4

• 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: trimethyl((1E,3E)-3-methyl-4-phenylbuta-1,3-dienyl)silane
• 英文别名: trimethyl-[(1E,3E)-3-methyl-4-phenylbuta-1,3-dienyl]silane
• CAS: 116973-01-4
• 化学式: C₁₄H₂₀Si
• 分子量: 216.398
• InChiKey: PZJMOVRFYAQARU-AQASXUMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.52
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  trimethyl((1E,3E)-3-methyl-4-phenylbuta-1,3-dienyl)silane 在 fructose-derived chiral ketone Sodium tetraborate decahydrate 、 Oxone 、 potassium carbonate 作用下， 以 水 、 乙腈 为溶剂， 反应 1.5h， 生成 trimethyl-[3-(2-methyl-3-phenyloxiran-2-yl)oxiran-2-yl]silane 、 (S,S)-2-methyl-2-[trans-2-(trimethylsilyl)vinyl]-3-phenyloxirane 、 (R,R)-2-methyl-2-[trans-2-(trimethylsilyl)vinyl]-3-phenyloxirane 、 trimethyl-[(2R,3R)-3-[(E)-1-phenylprop-1-en-2-yl]oxiran-2-yl]silane
  参考文献：
  名称：

  Highly Regio- and Enantioselective Monoepoxidation of Conjugated Dienes

  摘要：

  This paper describes a highly effective and mild asymmetric monoepoxidation method for conjugated dienes using a fructose-derived chiral ketone 1 as catalyst and Oxone as oxidant. The regioselectivies and enantioslectivies are very high in most cases. For unsymmetrical dienes, the regioselectivity can be regulated by using steric and electronic control. The olefin substrates include trans-disubstituted and trisubstituted olefins that can bear a wide range of functional groups such as hydroxyl groups, TBS ethers, or esters. The enantiomeric excesses for the major monoepoxides range from 89% to 97%. The epoxidation is believed to proceed via a spiro mode.

  DOI：

  10.1021/jo9721195
• 作为产物：
  描述：

  O-sec-butyl-S-3-methyl-4-oxo-4-phenyl-1-(trimethylsilyl)butyl carbonodithioate 在 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 间氯过氧苯甲酸 作用下， 以 二苯醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 3.0h， 生成 trimethyl((1E,3E)-3-methyl-4-phenylbuta-1,3-dienyl)silane
  参考文献：
  名称：

  A Synthesis of (1E,3E)-TMS Dienes from Keto-Xanthates via Chugaev-Type Elimination

  摘要：

  An efficient route leading to exclusively (1E,3E)-TMS dienes is described. Radical xanthate addition of keto-xanthates to vinyltrimethylsilane followed by one-pot Chugaev elimination/cyclization and in situ oxidation with m-CPBA afforded the corresponding TMS 2-sulfolenes. Isomerization to 3-sulfolenes by the action of DBU with the extrusion of sulfur dioxide in refluxing toluene gave the titled (1E,3E)-TMS dienes.

  DOI：

  10.1021/jo402169v

文献信息

• Regioselective alkylation and olefination of allylic carbanion stabilized by two different heteroatoms: phosphorus and silicon
  作者：Bum Sung Lee、Jun Mo Gil、Dong Young Oh

  DOI：10.1016/s0040-4039(01)00170-8

  日期：2001.3

  with LiHMDS, followed by successive addition of chlorotrimethylsilane and carbonyl reagent, afforded dienylsilanes in good yields. 3-Substituted dienylsilanes were obtained by alkylation and olefination of allylic carbanion of 3-trimethylsilylallylphosphonates.

  用LiHMDS处理烯丙基膦酸酯，然后连续加入氯代三甲基硅烷和羰基试剂，以高收率得到二烯基硅烷。通过3-三甲基甲硅烷基烯丙基膦酸酯的烯丙基碳负离子的烷基化和烯化获得3-取代的二烯基硅烷。
• Ni, Zhi-Jie; Yang, Pin-Fan; Ng, Dennis K. P., Journal of the American Chemical Society, 1990, vol. 112, # 25, p. 9356 - 9364
  作者：Ni, Zhi-Jie、Yang, Pin-Fan、Ng, Dennis K. P.、Tzeng, Yih-Ling、Luh, Tien-Yau

  DOI：——

  日期：——
• Transition-metal-promoted reactions. 25. Regioselective silylolefination of allylic dithioacetals. Stereoselective synthesis of 1-(trimethylsilyl)butadienes
  作者：Zhi Jie Ni、Tien Yau Luh

  DOI：10.1021/jo00258a047

  日期：1988.11
• PALOMO, CLAUDIO;AIZPURUA, JESUS M.;GARCIA, JESUS M.;GANBOA, INAKI;COSSIO,+, J. ORG. CHEM., 55,(1990) N, C. 2498-2503
  作者：PALOMO, CLAUDIO、AIZPURUA, JESUS M.、GARCIA, JESUS M.、GANBOA, INAKI、COSSIO,+

  DOI：——

  日期：——
• NI, ZHI-JIE;YANG, PIN-FAN;NG, DENNIS K. P.;TZENG, YIH-LING;LUH, TIEN-YAU, J. AMER. CHEM. SOC., 112,(1990) N5, C. 9356-9364
  作者：NI, ZHI-JIE、YANG, PIN-FAN、NG, DENNIS K. P.、TZENG, YIH-LING、LUH, TIEN-YAU

  DOI：——

  日期：——