(S)-4-methoxybenzyl 3,7-dimethyl-6-octenyl ether | 934704-86-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (S)-4-methoxybenzyl 3,7-dimethyl-6-octenyl ether
• CAS: 934704-86-6
• 化学式: C₁₈H₂₈O₂
• 分子量: 276.419
• InChiKey: RUVCAMNECQNPDR-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.98
• 重原子数：
  20.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (S)-4-methoxybenzyl 3,7-dimethyl-6-octenyl ether 在 吡啶 、 4-二甲氨基吡啶 、 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 、 三氟化硼乙醚 、 碘 、 sodium hexamethyldisilazane 、 双(三甲基硅烷基)氨基钾 、 potassium carbonate 、 戴斯-马丁氧化剂 、 magnesium 、 二甲基亚砜 、 苯硫酚 、 三乙胺 、 N,N-二异丙基乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 甲苯 、 叔丁醇 为溶剂， 反应 32.25h， 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)-(-)-β-香茅醇 、 4-甲氧基溴苄 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以100%的产率得到(S)-4-methoxybenzyl 3,7-dimethyl-6-octenyl ether
  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

文献信息

• Structure–activity relationship of α hormones, the mating factors of phytopathogen Phytophthora
  作者：Shylaja D. Molli、Jianhua Qi、Arata Yajima、Keisuke Shikai、Tadashi Imaoka、Tomoo Nukada、Goro Yabuta、Makoto Ojika

  DOI：10.1016/j.bmc.2011.12.015

  日期：2012.1

  The mating hormones alpha 1 and alpha 2 induce sexual reproduction of the phytopathogenic genus Phytophthora. To demonstrate the structural elements responsible to hormonal activity, 17 derivatives of alpha 1 and alpha 2 were synthesized and their hormonal activity (oospore-inducing activity) was evaluated. The terminal ester derivatives of alpha 1 (diacetate and dibenzoate) retained the hormonal activity, whereas a dicarbamate derivative completely suppressed the activity. Even monocarbamates showed weak activities; among them the 1-O-carbamate was less active than 16-O-carbamate, suggesting that the 1-OH group is a little more important than 16-OH. Dihydro, dehydro, and demethyl derivatives exhibited the minimum level of activity. Surviving activity of 15-epi-alpha 1 suggested a less importance of this stereochemistry. Contrary to alpha 1, not only the terminal diacetate derivative but also monoacetates of alpha 2 exhibited no or little activity. Among the monoacetates, 1-O-acetyl-alpha 2 exhibited little yet relatively better activity than the others. No activity was observed for mono- and dicarbamoyl derivatives of alpha 2. Dihydro alpha 2 with the saturated double bond lost most of the activity. These findings suggest that both the mating hormones alpha 1 and alpha 2 require most of the functional (hydroxyl, keto, and olefinic) groups they possess in their natural form for inducing the sexual reproduction of Phytophthora. (C) 2011 Elsevier Ltd. All rights reserved.