11-[5-(11-oxo-undec-9-en-1-ynyl)-furan-2-yl]-undec-2-en-10-ynal | 227751-02-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 11-[5-(11-oxo-undec-9-en-1-ynyl)-furan-2-yl]-undec-2-en-10-ynal
• 英文别名: (E)-11-[5-[(E)-11-oxoundec-9-en-1-ynyl]furan-2-yl]undec-2-en-10-ynal
• CAS: 227751-02-2
• 化学式: C₂₆H₃₂O₃
• 分子量: 392.538
• InChiKey: MZGMQFXYWZGHRN-HBKJEHTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  29
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  47.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  11-[5-(11-oxo-undec-9-en-1-ynyl)-furan-2-yl]-undec-2-en-10-ynal 在 lithium hydroxide 、 Dimethylzinc 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 82.5h， 生成
  参考文献：
  名称：

  Catalytic Enantioselective Synthesis of Adociacetylene B

  摘要：

  A catalytic enantioselective total synthesis of adociacetylene B (2) in five steps is reported. The efficiency of this synthesis was enabled by an asymmetric zinc alkynylation catalyzed by the proline-derived ligand (1).

  DOI：

  10.1021/ol0615836
• 作为产物：
  描述：

  undeca-2,10-diyn-1-ol 在 indium(III) triflate 、 四(三苯基膦)钯 、 (η5-indenyl)ruthenium(bis(triphenylphosphine))chloride 四氢吡咯 、 camphor-10-sulfonic acid 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 11-[5-(11-oxo-undec-9-en-1-ynyl)-furan-2-yl]-undec-2-en-10-ynal
  参考文献：
  名称：

  Catalytic Enantioselective Synthesis of Adociacetylene B

  摘要：

  A catalytic enantioselective total synthesis of adociacetylene B (2) in five steps is reported. The efficiency of this synthesis was enabled by an asymmetric zinc alkynylation catalyzed by the proline-derived ligand (1).

  DOI：

  10.1021/ol0615836

文献信息

• A Synthesis of Petrofuran Based on the Enantioselective Reduction of 1-Trimethylsilyl-4-alken-1-yn-3-ones
  作者：J. Garcia、M. López、J. Romeu

  DOI：10.1055/s-1999-6183

  日期：1999.4

  Highly enantioenriched 4-alken-1-yn-3-ol moiety (1), present in many bioactive acetylenic metabolites from sponges, has been efficiently obtained by reduction of the parent 1-trimethyl-silyl-4-alken-1-yn-3-one (2) with Alpine-Borane or with BH3 · SMe2 in the presence of chiral oxazaborolidines, followed by desilylation of the resulting alcohol. This strategy has been applied to the first stereoselective synthesis of petrofuran 3.

  高度对映体富集的 4-alken-1-yn-3-ol 部分 (1) 存在于海绵的许多生物活性炔属代谢物中，通过还原母体 1-三甲基-甲硅烷基-4-alken-1-yn- 可以有效获得在手性恶唑硼烷存在下，与 Alpine-Borane 或 BH3·SMe2 进行 3-一 (2) 反应，然后对所得醇进行脱甲硅烷基化。该策略已应用于石油呋喃3的首次立体选择性合成。
• A concise synthesis of (+)- and (−)-adociacetylene B
  作者：Benjamin W Gung、Hamilton Dickson、Stephany Shockley

  DOI：10.1016/s0040-4039(01)00879-6

  日期：2001.7

  The syllthesis of (-)-adociacetylene B was completed in six steps in a yield of 9.3% while the (+)-enantiomer was synthesized in seven steps and 7.5%. An enzymatic resolution of racemic I using the lipase from Pseudomonas sp. was employed to obtain (+) and (-)-1. This synthesis of (S,S)-1 represents the first total synthesis of a naturally occurring acetylenic alcohol that has two chiral centers and four acetylene units. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Catalytic Enantioselective Synthesis of Adociacetylene B
  作者：Barry M. Trost、Andrew H. Weiss

  DOI：10.1021/ol0615836

  日期：2006.9.1

  A catalytic enantioselective total synthesis of adociacetylene B (2) in five steps is reported. The efficiency of this synthesis was enabled by an asymmetric zinc alkynylation catalyzed by the proline-derived ligand (1).