acetic acid 1-but-3-enyl-2-hydroxyhex-5-enyl ester | 912295-20-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子
• 英文名称: acetic acid 1-but-3-enyl-2-hydroxyhex-5-enyl ester
• 英文别名: [(5R,6R)-6-hydroxydeca-1,9-dien-5-yl] acetate
• CAS: 912295-20-6
• 化学式: C₁₂H₂₀O₃
• 分子量: 212.289
• InChiKey: DXBQSWVVZXFIJM-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  acetic acid 1-but-3-enyl-2-hydroxyhex-5-enyl ester 在 咪唑 、 叔丁基过氧化氢 、 Co(II) (modp)2 、 Co(II)(modp)2 、 乙基溴化镁 、 氧气 作用下， 以 异辛烷 、 乙醚 、 水 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 50.0 ℃ 、101.33 kPa 条件下， 反应 17.0h， 生成 (2R,2R',5R, 5R')-[5-(5'-(tert-butyldimethylsilyloxy)methyltetrahydrofuran-2'-yl)tetrahydrofuran-2-yl]methanol
  参考文献：
  名称：

  Advances in Lewis Acid Controlled Carbon−Carbon Bond-Forming Reactions Enable a Concise and Convergent Total Synthesis of Bullatacin

  摘要：

  Lewis acids control regioselectivity in the alkylation of epi-chlorohydrin and the stereochemistry of an alkyne addition to set the C24/C23 anti relationship. These advances facilitate an efficient total synthesis of bullatacin in 13.3% overall yield from commercial starting materials.

  DOI：

  10.1021/ol061847o
• 作为产物：
  描述：

  原乙酸三乙酯 、 (5R,6R)-5,6-dihydroxydeca-1,9-diene 在 对甲苯磺酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 10.0h， 以99%的产率得到acetic acid 1-but-3-enyl-2-hydroxyhex-5-enyl ester
  参考文献：
  名称：

  Advances in Lewis Acid Controlled Carbon−Carbon Bond-Forming Reactions Enable a Concise and Convergent Total Synthesis of Bullatacin

  摘要：

  Lewis acids control regioselectivity in the alkylation of epi-chlorohydrin and the stereochemistry of an alkyne addition to set the C24/C23 anti relationship. These advances facilitate an efficient total synthesis of bullatacin in 13.3% overall yield from commercial starting materials.

  DOI：

  10.1021/ol061847o

文献信息

• Increased Yields and Simplified Purification with a Second-Generation Cobalt Catalyst for the Oxidative Formation of <i>trans</i>-THF Rings
  作者：Cory Palmer、Nicholas A. Morra、Andrew C. Stevens、Barbora Bajtos、Ben P. Machin、Brian L. Pagenkopf

  DOI：10.1021/ol9023375

  日期：2009.12.17

  The synthesis of a second-generation cobalt catalyst for the formation of trans-THF products via the Mukaiyama aerobic oxidative cyclization is reported. Two procedures have been developed with the new water-soluble catalyst that give superior yields and greatly simplify purification compared to the previous catalysts.

  据报道，通过Mukaiyama好氧氧化环化反应合成了第二代钴催化剂，以形成反式THF产物。与以前的催化剂相比，使用这种新型水溶性催化剂开发了两种方法，它们具有较高的收率并大大简化了纯化过程。
• Synthesis of 10 stereochemically distinct bis-tetrahydrofuran intermediates for creating a library of 64 asimicin stereoisomers
  作者：Zhiyong Chen、Subhash C. Sinha

  DOI：10.1016/j.tetlet.2009.08.082

  日期：2009.11

  Stereoselective synthesis of 10 unique bifunctional stereoisomeric adjacent bis-THF intermediates (R = Bz), including 5.1-5.4, 5.7-5.9, 5.11, and 5.15-5.16, of 16 possible compounds, is described. The key steps used in the synthesis of these compounds included the rhenium(VII) oxide-mediated and the Co(modP)(2)-catalyzed trans oxidative cyclizations (OCs), the OsO4-catalyzed cis OC, and the Williamson's type etherification reactions. The remaining six bis-THF intermediates (R = Bn) can be prepared from 5.7-5.9, 5.11, and 5.15-5.16 (R = Bz) in two steps, including protection of the free alcohol as benzyl ether followed by the benzoate deprotection. These intermediates should provide access to all 64 asimicin stereoisomers; and their analogs. (C) 2009 Published by Elsevier Ltd.