(7R,9R)-11-(4-Methoxy-benzyloxy)-7-methoxymethoxy-9-methyl-undec-1-en-6-ol | 934705-30-3

• 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: (7R,9R)-11-(4-Methoxy-benzyloxy)-7-methoxymethoxy-9-methyl-undec-1-en-6-ol
• CAS: 934705-30-3
• 化学式: C₂₂H₃₆O₅
• 分子量: 380.525
• InChiKey: YAXHOIHLLKYELG-MCGPBEARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.33
• 重原子数：
  27.0
• 可旋转键数：
  16.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (7R,9R)-11-(4-Methoxy-benzyloxy)-7-methoxymethoxy-9-methyl-undec-1-en-6-ol 在 吡啶 、 camphor-10-sulfonic acid 、 双(三甲基硅烷基)氨基钾 、 戴斯-马丁氧化剂 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 甲苯 、 苯 为溶剂， 反应 0.91h， 生成
  参考文献：
  名称：

  Exploration of conjugate addition routes to advanced tricyclic components of mangicol A

  摘要：

  Two synthetic approaches to the cytotoxic marine natural product known as mangicol A are described. The starting material common to both pathways is the cyclopentenonecarboxylate 11. The first tactic involves the 1,4-addition to 11 of the cuprate derivable from iodide 10, while the second proceeds via base-promoted conjugate addition of the regiospecifically generated enolate anion of 41. The first strategy proceeds by a series of efficient steps to tricyclic aldol 21 and subsequently to beta-diketone 7. The latter proved to be totally unresponsive to schemes aimed at introduction of a butenyl group. The second approach involves earlier introduction of this substituent as realized in stereo-controlled fashion via transition state 42. While further passage to 44 proved uneventful, this advanced intermediate and analogs thereof proved remarkably recalcitrant to cyclization in the precedented fashion. In no instance was generation of a suitable product realized. These studies serve to underscore the extent to which steric considerations can complicate matters and the extent to which they must be skirted. Finally, a direct enantioselective route to the side chain aldehyde 2 is detailed. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.03.066
• 作为产物：
  描述：

  (S)-4-methoxybenzyl 3,7-dimethyl-6-octenyl ether 在 sodium chlorite 、 sodium periodate 、 sodium dihydrogenphosphate 、 四氧化锇 、 锂硼氢 、 正丁基锂 、 N-甲基吲哚酮 、 2-甲基-2-丁烯 、 草酰氯 、 碘 、 sodium hexamethyldisilazane 、 magnesium 、 二甲基亚砜 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 24.17h， 生成 (7R,9R)-11-(4-Methoxy-benzyloxy)-7-methoxymethoxy-9-methyl-undec-1-en-6-ol
  参考文献：
  名称：

  Exploration of conjugate addition routes to advanced tricyclic components of mangicol A

  摘要：

  Two synthetic approaches to the cytotoxic marine natural product known as mangicol A are described. The starting material common to both pathways is the cyclopentenonecarboxylate 11. The first tactic involves the 1,4-addition to 11 of the cuprate derivable from iodide 10, while the second proceeds via base-promoted conjugate addition of the regiospecifically generated enolate anion of 41. The first strategy proceeds by a series of efficient steps to tricyclic aldol 21 and subsequently to beta-diketone 7. The latter proved to be totally unresponsive to schemes aimed at introduction of a butenyl group. The second approach involves earlier introduction of this substituent as realized in stereo-controlled fashion via transition state 42. While further passage to 44 proved uneventful, this advanced intermediate and analogs thereof proved remarkably recalcitrant to cyclization in the precedented fashion. In no instance was generation of a suitable product realized. These studies serve to underscore the extent to which steric considerations can complicate matters and the extent to which they must be skirted. Finally, a direct enantioselective route to the side chain aldehyde 2 is detailed. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.03.066