(E)-tert-butyldimethyl((1,4-diphenylbut-3-en-1-yl)oxy)dimethylsilane | 1229597-20-9

• 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: (E)-tert-butyldimethyl((1,4-diphenylbut-3-en-1-yl)oxy)dimethylsilane
• 英文别名: (E)-tert-butyl((1,4-diphenylbut-3-en-1-yl)oxy)dimethylsilane
• CAS: 1229597-20-9
• 化学式: C₂₂H₃₀OSi
• 分子量: 338.565
• InChiKey: BEWRKYBYZVYLBJ-NTCAYCPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.85
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  2-phenyl[1,3,2]dioxaborolane 、 4-(tert-butyldimethylsilyloxy)-4-phenylbut-1-ene 在 氧气 、 palladium diacetate 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 40.0 ℃ 、101.33 kPa 条件下， 反应 48.0h， 以65%的产率得到(E)-tert-butyldimethyl((1,4-diphenylbut-3-en-1-yl)oxy)dimethylsilane
  参考文献：
  名称：

  共轭微孔聚合物作为多相配体用于高选择性氧化 Heck 反应

  摘要：

  设计并合成了一系列含有 C≡C 键的吡啶型配体用于选择性氧化 Heck 反应。这些配体被用作功能单元并整合到共轭微孔聚合物的骨架中。6,6'-二碘-2,2'-联吡啶和1,3,5-三乙炔苯通过Sonogashira交叉偶联策略缩聚得到CMP-1材料。所得的 CMP-1 用作 PdII 催化的氧化 Heck 反应的多相催化配体，具有高线性选择性。CMP-1 的线性选择性比基于联吡啶的单体配体高约 30 倍。这项工作开辟了使用 CMP 作为开发高效催化剂控制有机反应区域选择性的有趣平台的新前沿。

  DOI：

  10.1021/jacs.7b00643

文献信息

• Thiophene-Alkyne-Based CMPs as Highly Selective Regulators for Oxidative Heck Reaction
  作者：Ren-Hao Li、Zong-Cang Ding、Cun-Yao Li、Jun-Jia Chen、Yun-Bing Zhou、Xiao-Ming An、Yun-Jie Ding、Zhuang-Ping Zhan

  DOI：10.1021/acs.orglett.7b01858

  日期：2017.9.1

  as ligands for PdII-promoted organic reactions are reported for the first time. These ligands were utilized as catalytic sites and integrated into the skeleton of conjugated microporous polymers. By employing these CMP materials as selective regulators, oxidative Heck reactions between arylboronic esters and electronically unbiased alkenes provide highly selective linear products.

  首次报道了含有相邻的C≡C基团作为Pd II促进的有机反应的配体的噻吩。这些配体被用作催化位点并整合到共轭微孔聚合物的骨架中。通过将这些CMP材料用作选择性调节剂，芳基硼酸酯与电子无偏烯烃之间的氧化Heck反应可提供高度选择性的线性产物。
• A Highly Selective and General Palladium Catalyst for the Oxidative Heck Reaction of Electronically Nonbiased Olefins
  作者：Erik W. Werner、Matthew S. Sigman

  DOI：10.1021/ja1060998

  日期：2010.10.13

  A general, highly selective oxidative Heck reaction is reported. The reaction is high-yielding under mild conditions without the need for base or high temperatures, and the selectivity is excellent, without the requirement for electronically biased olefins or other specific directing groups. A preliminary mechanistic investigation suggests that the unusually high selectivity may be due to the catalyst's sensitivity to C-H bond strength in the selectivity-determining beta-hydride elimination step.
• Pd^II-Catalyzed Oxidative 1,1-Diarylation of Terminal Olefins
  作者：Erik W. Werner、Kaveri B. Urkalan、Matthew S. Sigman

  DOI：10.1021/ol1009575

  日期：2010.6.18

  Evaluation of the scope of a Pd-II-catalyzed oxidative 1,1-diarylation reaction of terminal olefins using aryl stannanes is reported. The reaction is shown to be tolerant of functionality commonly encountered in organic synthesis; however, the reaction outcome was found to be dependent on the nature of the aryl stannane used. A mechanistic rationale for the observation of this influence is provided.