(Z)-(R)-8-((S)-2-Benzyloxymethyl-1-methyl-cyclopent-2-enyl)-1-(tert-butyl-dimethyl-silanyloxy)-2,6-dimethyl-oct-6-en-4-one | 871823-44-8

• 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: (Z)-(R)-8-((S)-2-Benzyloxymethyl-1-methyl-cyclopent-2-enyl)-1-(tert-butyl-dimethyl-silanyloxy)-2,6-dimethyl-oct-6-en-4-one
• 英文别名: (Z,2R)-1-[tert-butyl(dimethyl)silyl]oxy-2,6-dimethyl-8-[(1S)-1-methyl-2-(phenylmethoxymethyl)cyclopent-2-en-1-yl]oct-6-en-4-one
• CAS: 871823-44-8
• 化学式: C₃₀H₄₈O₃Si
• 分子量: 484.795
• InChiKey: KQCLHEKUVDDDPD-QZHHIYDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.27
• 重原子数：
  34
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-(R)-8-((S)-2-Benzyloxymethyl-1-methyl-cyclopent-2-enyl)-1-(tert-butyl-dimethyl-silanyloxy)-2,6-dimethyl-oct-6-en-4-one 在 18-冠醚-6 、 4-甲基苯磺酸吡啶 咪唑 、 氟化铵 、 sodium tetrahydroborate 、 邻苯二甲酸二甲酯 、 碘 、 lithium dihydronaphthylide radical 、 triethylamine tris(hydrogen fluoride) 、 N,N-二异丙基乙胺 、 三苯基膦 、 lithium hexamethyldisilazane 作用下， 以 甲醇 为溶剂， 生成 (Z)-(6R,12aS)-4-((E)-2-Ethoxy-vinyloxy)-8-methoxymethoxy-6,10,12a-trimethyl-1,2,4,5,6,7,8,9,12,12a-decahydro-cyclopentacycloundecene-4-carbonitrile
  参考文献：
  名称：

  General synthetic approach to bicyclo[9.3.0]tetradecenone: a versatile intermediate to clavulactone and clavirolides

  摘要：

  An efficient and stereoselective approach to the bicyclo[9.3.0]tetradecenone core structure of clavulactone starting from readily and abundantly available 2-methyl-1,3-cyclopentandione employing microbial desymmetrization and cyanohydrin alkylation as the key steps is described. The synthetic route described herein is applicable to the syntheses of the core structures of Clavirolides A-F. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.09.106
• 作为产物：
  描述：

  2-烯丙基-2-甲基-1,3-环戊二酮 在 四氧化锇 、 4-甲基苯磺酸吡啶 、 镍 咪唑 、 甲醇 、 sodium hydroxide 、 N-甲基吲哚酮 、 baker's yeast 、 三氟化硼乙醚 、 sodium hexamethyldisilazane 、 sodium hydride 、 戴斯-马丁氧化剂 、 甲基磺酰氯 、 过碘酸 、 三乙胺 、 lithium chloride 作用下， 以 水 、 乙酸乙酯 为溶剂， 生成 (Z)-(R)-8-((S)-2-Benzyloxymethyl-1-methyl-cyclopent-2-enyl)-1-(tert-butyl-dimethyl-silanyloxy)-2,6-dimethyl-oct-6-en-4-one
  参考文献：
  名称：

  General synthetic approach to bicyclo[9.3.0]tetradecenone: a versatile intermediate to clavulactone and clavirolides

  摘要：

  An efficient and stereoselective approach to the bicyclo[9.3.0]tetradecenone core structure of clavulactone starting from readily and abundantly available 2-methyl-1,3-cyclopentandione employing microbial desymmetrization and cyanohydrin alkylation as the key steps is described. The synthetic route described herein is applicable to the syntheses of the core structures of Clavirolides A-F. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.09.106

文献信息

• Stereospecific rearrangement of α-hydroxyepoxide: efficient approach to the trans-bicyclo[9.3.0]tetradecane core en route to clavulactone
  作者：Bingfeng Sun、Xingxiang Xu

  DOI：10.1016/j.tetlet.2005.11.021

  日期：2006.1

  We document a synthetic route to trans-bicyclo[9.3.0]tetradecanes. The strategy is based oil a quantitative and stereospecific Lewis acid mediated rearrangement of alpha-hydroxyepoxide to beta-hydroxyketone, which paved the way for the synthesis of clavulactone and clavirolides. (c) 2005 Elsevier Ltd. All rights reserved.
• General synthetic approach to bicyclo[9.3.0]tetradecenone: a versatile intermediate to clavulactone and clavirolides
  作者：Bingfeng Sun、Xingxiang Xu

  DOI：10.1016/j.tetlet.2005.09.106

  日期：2005.11

  An efficient and stereoselective approach to the bicyclo[9.3.0]tetradecenone core structure of clavulactone starting from readily and abundantly available 2-methyl-1,3-cyclopentandione employing microbial desymmetrization and cyanohydrin alkylation as the key steps is described. The synthetic route described herein is applicable to the syntheses of the core structures of Clavirolides A-F. (c) 2005 Elsevier Ltd. All rights reserved.