(E)-6-[tert-butyl(dimethyl)silyl]oxyhex-4-en-2-yn-1-ol | 220811-69-8

• 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: (E)-6-[tert-butyl(dimethyl)silyl]oxyhex-4-en-2-yn-1-ol
• CAS: 220811-69-8
• 化学式: C₁₂H₂₂O₂Si
• 分子量: 226.391
• InChiKey: YPQPVYOZHMJMPU-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.56
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-6-[tert-butyl(dimethyl)silyl]oxyhex-4-en-2-yn-1-ol 在 bis-triphenylphosphine-palladium(II) chloride 草酰氯 、 二异丁基氢化铝 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 5.0h， 生成 [(2E,4Z,8E)-4-bromo-10-[tert-butyl(dimethyl)silyl]oxydeca-2,4,8-trien-6-ynoxy]-tert-butyl-dimethylsilane
  参考文献：
  名称：

  A highly efficient and selective synthesis of lissoclinolide featuring hydrogen transfer hydrozirconation,trans-selective Pd-catalyzed cross coupling of alkenylzirconiums with 1,1-dibromoalkenes and Ag-catalyzed lactonization providing(Z)-γ-alkylidenebutenolides

  摘要：

  An antibiotic lissoclinolide has been synthesized from propargyl alcohol in 9 steps and in 32% overall yield via (i) hydrogen transfer hydrozirconation of TBS-protected propargyl alcohol with i-BuZrCp2Cl, (ii) Pd-catalyzed trans-selective cross coupling of the hydrozirconation product with a key 1,1-dibromoalkene intermediate 5 and (iii) Ag-catalyzed lactonization of a trienynoic acid precursor 2. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02394-6
• 作为产物：
  描述：

  叔丁基二甲基(2-丙炔氧基)硅烷 在 四(三苯基膦)钯 四氢吡咯 、 chloro(cyclopentadienyl)isobutylzirconium(IV) 、 碘 作用下， 反应 0.5h， 生成 (E)-6-[tert-butyl(dimethyl)silyl]oxyhex-4-en-2-yn-1-ol
  参考文献：
  名称：

  A highly efficient and selective synthesis of lissoclinolide featuring hydrogen transfer hydrozirconation,trans-selective Pd-catalyzed cross coupling of alkenylzirconiums with 1,1-dibromoalkenes and Ag-catalyzed lactonization providing(Z)-γ-alkylidenebutenolides

  摘要：

  An antibiotic lissoclinolide has been synthesized from propargyl alcohol in 9 steps and in 32% overall yield via (i) hydrogen transfer hydrozirconation of TBS-protected propargyl alcohol with i-BuZrCp2Cl, (ii) Pd-catalyzed trans-selective cross coupling of the hydrozirconation product with a key 1,1-dibromoalkene intermediate 5 and (iii) Ag-catalyzed lactonization of a trienynoic acid precursor 2. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02394-6

文献信息

• Development of a Method for the Synthesis of a-Substituted a,b-Unsaturated Lactones Based on Stille-Type Pd-catalyzed Carbonylation of (Z)-w-Iodoalkenols. An Efficient and Selective Synthesis of (+)-Hamabiwa-lactone B
  作者：Ei-ichi Negishi、Baiqiao Liao

  DOI：10.3987/com-99-s138

  日期：——
• A highly efficient and selective synthesis of lissoclinolide featuring hydrogen transfer hydrozirconation,trans-selective Pd-catalyzed cross coupling of alkenylzirconiums with 1,1-dibromoalkenes and Ag-catalyzed lactonization providing(Z)-γ-alkylidenebutenolides
  作者：Caiding Xu、Ei-ichi Negishi

  DOI：10.1016/s0040-4039(98)02394-6

  日期：1999.1

  An antibiotic lissoclinolide has been synthesized from propargyl alcohol in 9 steps and in 32% overall yield via (i) hydrogen transfer hydrozirconation of TBS-protected propargyl alcohol with i-BuZrCp2Cl, (ii) Pd-catalyzed trans-selective cross coupling of the hydrozirconation product with a key 1,1-dibromoalkene intermediate 5 and (iii) Ag-catalyzed lactonization of a trienynoic acid precursor 2. (C) 1998 Elsevier Science Ltd. All rights reserved.