11-triethylsilylundec-10-yn-1-ol | 113308-98-8

• 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: 11-triethylsilylundec-10-yn-1-ol
• CAS: 113308-98-8
• 化学式: C₁₇H₃₄OSi
• 分子量: 282.542
• InChiKey: QMCOOVRGTPYOAX-UHFFFAOYSA-N

物化性质

• 沸点：
  347.3±15.0 °C(Predicted)
• 密度：
  0.867±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.15
• 重原子数：
  19.0
• 可旋转键数：
  11.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  11-triethylsilylundec-10-yn-1-ol 在 吡啶 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  A Pd(0)-Mediated Indole (Macro)cyclization Reaction

  摘要：

  Herein we report a systematic study of the Larock indole annulation designed to explore the scope and define the generality of its use in macrocyclization reactions, its use in directly accessing the chloropeptin I versus II DEF ring system as well as key unnatural isomers, its utility for both peptide-derived and more conventional carbon-chain based macrocycles, and its extension to intramolecular cyclizations with formation of common ring sizes. The studies define a powerful method complementary to the Stile or Suzuki cross-coupling reactions for the synthesis of cyclic or macrocyclic ring systems containing an embedded indole, tolerating numerous functional groups and incorporating various (up to 28-membered) ring sizes. As a result of the efforts to expand the usefulness and scope of the reaction, we also disclose a catalytic variant of the reaction, along with a powerful Pd-2(dba)(3)-derived catalyst system, and an examination of the factors impacting reactivity and catalysis.

  DOI：

  10.1021/ja3121394
• 作为产物：
  描述：

  10-十一碳炔酸 在 lithium aluminium tetrahydride 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.5h， 生成 11-triethylsilylundec-10-yn-1-ol
  参考文献：
  名称：

  A Pd(0)-Mediated Indole (Macro)cyclization Reaction

  摘要：

  Herein we report a systematic study of the Larock indole annulation designed to explore the scope and define the generality of its use in macrocyclization reactions, its use in directly accessing the chloropeptin I versus II DEF ring system as well as key unnatural isomers, its utility for both peptide-derived and more conventional carbon-chain based macrocycles, and its extension to intramolecular cyclizations with formation of common ring sizes. The studies define a powerful method complementary to the Stile or Suzuki cross-coupling reactions for the synthesis of cyclic or macrocyclic ring systems containing an embedded indole, tolerating numerous functional groups and incorporating various (up to 28-membered) ring sizes. As a result of the efforts to expand the usefulness and scope of the reaction, we also disclose a catalytic variant of the reaction, along with a powerful Pd-2(dba)(3)-derived catalyst system, and an examination of the factors impacting reactivity and catalysis.

  DOI：

  10.1021/ja3121394

文献信息

• Studies on the synthesis of linear aliphatic compounds. Part 2. The realisation of a strategy for repeated molecular doubling.
  作者：Eva Igner、Oliver I. Paynter、Derek J. Simmonds、Mark C. Whiting

  DOI：10.1039/p19870002447

  日期：——

  starting-materials, obtainable free from near homologues, to compounds of doubled chain length have been explored as approaches to the synthesis of n-paraffins and of terminally mono- or bi-functional derivatives. Acetylene alkylation routes lead to problems with protecting groups, but the use of the Wittig reaction provides a method of molecular doubling convenient for repeated use, with the formation of chain-lengths

  作为合成正链烷烃和末端单官能或双官能衍生物的方法，已探索了从C 11和C 12起始原料（几乎无同源物）到链长加倍的化合物的途径。乙炔烷基化途径导致保护基的问题，但是使用Wittig反应提供了一种方便重复使用的分子加倍方法，链长的形成以几何级数增加。讨论了非常长链烷烃合成中固有的一般问题，回顾了较早的工作，并提出了成功的标准。描述了对羟基有用的保护基，三对甲苯基甲基（三甲基）醚。