(2Z,6E)-8-[tert-butyl(dimethyl)silyl]oxy-2-[(E)-3-[tert-butyl(dimethyl)silyl]oxyprop-1-enyl]octa-2,6-dien-4-ynoic acid | 220811-65-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2Z,6E)-8-[tert-butyl(dimethyl)silyl]oxy-2-[(E)-3-[tert-butyl(dimethyl)silyl]oxyprop-1-enyl]octa-2,6-dien-4-ynoic acid
• CAS: 220811-65-4
• 化学式: C₂₃H₄₀O₄Si₂
• 分子量: 436.739
• InChiKey: DVPQIPBINKZMKL-LLBCWFSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.16
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2Z,6E)-8-[tert-butyl(dimethyl)silyl]oxy-2-[(E)-3-[tert-butyl(dimethyl)silyl]oxyprop-1-enyl]octa-2,6-dien-4-ynoic acid 在 氢氟酸 、 silver nitrate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 1.0h， 生成 lissoclinolide
  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：

  (E)-1-tert-butyldimethylsilyloxy-3-iodo-2-propene 在 bis-triphenylphosphine-palladium(II) chloride 、 四(三苯基膦)钯 四氢吡咯 、 草酰氯 、 叔丁基锂 、 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 5.5h， 生成 (2Z,6E)-8-[tert-butyl(dimethyl)silyl]oxy-2-[(E)-3-[tert-butyl(dimethyl)silyl]oxyprop-1-enyl]octa-2,6-dien-4-ynoic acid
  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

• 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.