4-((S)-2-Benzyloxymethyl-1-methyl-cyclopent-2-enylmethyl)-2,2-dimethyl-[1,3]dioxolane | 871823-29-9

• 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: 4-((S)-2-Benzyloxymethyl-1-methyl-cyclopent-2-enylmethyl)-2,2-dimethyl-[1,3]dioxolane
• 英文别名: 2,2-dimethyl-4-[[(1S)-1-methyl-2-(phenylmethoxymethyl)cyclopent-2-en-1-yl]methyl]-1,3-dioxolane
• CAS: 871823-29-9
• 化学式: C₂₀H₂₈O₃
• 分子量: 316.441
• InChiKey: IBTWVOLDLLYZIG-IJHRGXPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-((S)-2-Benzyloxymethyl-1-methyl-cyclopent-2-enylmethyl)-2,2-dimethyl-[1,3]dioxolane 在 4-甲基苯磺酸吡啶 甲醇 、 sodium hexamethyldisilazane 、 sodium hydride 、 甲基磺酰氯 、 过碘酸 、 三乙胺 、 lithium chloride 作用下， 以 乙酸乙酯 为溶剂， 生成 (Z)-6-((S)-2-Benzyloxymethyl-1-methyl-cyclopent-2-enyl)-2-hydroxy-2-((R)-3-hydroxy-2-methyl-propyl)-4-methyl-hex-4-enenitrile
  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 、 镍 N-甲基吲哚酮 、 baker's yeast 、 三氟化硼乙醚 、 sodium hydride 、 戴斯-马丁氧化剂 作用下， 生成 4-((S)-2-Benzyloxymethyl-1-methyl-cyclopent-2-enylmethyl)-2,2-dimethyl-[1,3]dioxolane
  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

• 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.