(9E)-(2S*,3S*,6R*,7R*)-2,3;6,7-diepoxy-3,7,11,11-tetramethylcycloundec-9-ene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: (9E)-(2S*,3S*,6R*,7R*)-2,3;6,7-diepoxy-3,7,11,11-tetramethylcycloundec-9-ene
• 英文别名: (1S,4R,6R,8E,12S)-1,6,10,10-tetramethyl-5,13-dioxatricyclo[10.1.0.04,6]tridec-8-ene
• 化学式: C₁₅H₂₄O₂
• 分子量: 236.354
• InChiKey: UFBUQKAQYQDEOE-SJFFUCJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  25.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (9E)-(2S*,3S*,6R*,7R*)-2,3;6,7-diepoxy-3,7,11,11-tetramethylcycloundec-9-ene 在 2,2,6,6-四甲基哌啶 、 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 生成 (2R^*,6S^*)-2,6-dihydroxyhumla-9(E)-3(12),7(13),9-triene
  参考文献：
  名称：

  Takeda, Satoshi; Iimura, Yasuhiro; Tanaka, Kazunori, Chemistry Letters, 1990, p. 155 - 156

  摘要：

  DOI：
• 作为产物：
  描述：

  大麻 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 (9E)-(2S*,3S*,6R*,7R*)-2,3;6,7-diepoxy-3,7,11,11-tetramethylcycloundec-9-ene
  参考文献：
  名称：

  Takeda, Satoshi; Iimura, Yasuhiro; Tanaka, Kazunori, Chemistry Letters, 1990, p. 155 - 156

  摘要：

  DOI：

文献信息

• Where is the Oxygen? Structural Analysis of α-Humulene Oxidation Products by the Crystalline Sponge Method
  作者：Nicolas Zigon、Manabu Hoshino、Shota Yoshioka、Yasuhide Inokuma、Makoto Fujita

  DOI：10.1002/anie.201502302

  日期：2015.7.27

  Crystal structures of α‐humulene, a cyclic sesquiterpene, and its oxidized subproducts, were analyzed by the crystalline sponge method. Regio‐ and stereochemistry, including absolute configuration when a chiral oxidant was applied, and the stable conformations of all the scaffold‐related compounds were successfully determined for samples on a 5–50 μg scale.

  通过结晶海绵法分析了α-hu草烯，环状倍半萜烯及其氧化副产物的晶体结构。区域化学和立体化学，包括使用手性氧化剂时的绝对构型，并成功测定了5-50μg规模的样品中所有与脚手架相关的化合物的稳定构象。
• First Isolation and Determination of Three Humulene Triepoxides
  作者：Kiyoharu Hayano、Katsura Mochizuki

  DOI：10.3987/com-97-7838

  日期：——

  The epoxidation of(9E)-(2R*, 3R*, 6R*, 7R*)-2,3;6,7-diepoxy-3,7, 11,11-tetramethylcycloundec-9-ene (1TC) with m-CPBA gave two triepoxides, (2R*, 3R*, 6R*, 7R*, 9S*, 10S*)- and (2R*, 3R*, 6R*, 7R*, 9R*, 10R*)-2,3; 6,7;9,10-triepoxy-3,7,11,11-tetramethylcycloundecane (3 and 4), in the ratio of 3 :4 = 52:48. The epoxidation of (9E)-(2S*, 3S*, 6R*, 7R*)-2,3;6,7-diepoxy-3,7,11,11 -tetramethylcycloundec-9-ene (2CT) gave only one triepoxide, (2S*, 3S*, 6R*, 7R*, 9S*, 10S*)-2,3;6,7;9,10-triepoxy-3,7,11,11-tetramethylcycloundecane (5). The configurations for 4 and 5 were determined by X-Ray crystallography.
• Hydrolysis products of humulene diepoxide A
  作者：Robert J. Smith、Belaid Mahiou、Max L. Deinzer

  DOI：10.1016/s0040-4020(01)80933-9

  日期：1991.1

  Humulene diepoxide A, a flavoring compound found in hops, undergoes hydrolysis reactions upon boiling at pH 4. More than ten hydrolysis products were produced, of which five, 1-5 have been isolated and their structures determined. Two of these compounds, 1 and 2, are diastereomeric humuladiene triols, one is an exo-methylene diol 3, another is a saturated tricyclic triol 4, and the last is a bicyclic triol with an exo-methylene group 5. Aroma/flavor profiles of compounds 1 and 2 indicate that 2 would be more desirable than 1 in brewing.