((2R,5R)-5-((R)-1-hydroxypent-4-enyl)tetrahydrofuran-2-yl)methyl benzoate | 1011298-63-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ((2R,5R)-5-((R)-1-hydroxypent-4-enyl)tetrahydrofuran-2-yl)methyl benzoate
• 英文别名: [(2R,5R)-5-[(1R)-1-hydroxypent-4-enyl]oxolan-2-yl]methyl benzoate
• CAS: 1011298-63-7
• 化学式: C₁₇H₂₂O₄
• 分子量: 290.359
• InChiKey: AXNJMRCCVHOTOS-BZUAXINKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  ((2R,5R)-5-((R)-1-hydroxypent-4-enyl)tetrahydrofuran-2-yl)methyl benzoate 在 叔丁基过氧化氢 、 bis(1-morpholinocarbamoyl-4,4-dimethyl-1,3-pentanedionato)cobalt(II) 作用下， 以 癸烷 、 水 、 异丙醇 为溶剂， 50.0 ℃ 、101.33 kPa 条件下， 以67%的产率得到((2R,2'R,5R,5'R)-5'-(hydroxymethyl)octahydro-2,2'-bifuranyl-5-yl)methyl benzoate
  参考文献：
  名称：

  Synthesis of 10 stereochemically distinct bis-tetrahydrofuran intermediates for creating a library of 64 asimicin stereoisomers

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2009.08.082
• 作为产物：
  描述：

  (R,E)-2-hydroxydeca-5,9-dienyl benzoate 在 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 ((2R,5R)-5-((R)-1-hydroxypent-4-enyl)tetrahydrofuran-2-yl)methyl benzoate
  参考文献：
  名称：

  Total synthesis of 27-hydroxy-bullatacin and its C-15 epimer, and studies on their inhibitory effect on bovine heart mitochondrial complex I functions

  摘要：

  The total synthesis of 27-hydroxybullatacin and its C-15 epimer has been achieved using rhenium(VII) oxides-mediated and Co(modp)(2)-catalyzed oxidative cyclization (OC), diastereoselective alkynylation, Brown's enantioselective allylboration, and Grubbs' cross metathesis as the key reactions. The inhibitory effect of these compounds on the complex I function, as determined by using bovine submitochondrial particles, was in low nanomolar range. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.11.089

文献信息

• Total synthesis of 27-hydroxy-bullatacin and its C-15 epimer, and studies on their inhibitory effect on bovine heart mitochondrial complex I functions
  作者：Zhiyong Chen、Subhash C. Sinha

  DOI：10.1016/j.tet.2007.11.089

  日期：2008.2

  The total synthesis of 27-hydroxybullatacin and its C-15 epimer has been achieved using rhenium(VII) oxides-mediated and Co(modp)(2)-catalyzed oxidative cyclization (OC), diastereoselective alkynylation, Brown's enantioselective allylboration, and Grubbs' cross metathesis as the key reactions. The inhibitory effect of these compounds on the complex I function, as determined by using bovine submitochondrial particles, was in low nanomolar range. (C) 2007 Elsevier Ltd. All rights reserved.
• 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.