enokipodin C | 359701-26-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: enokipodin C
• 英文别名: (1R,9R,11R)-1,5,12,12-tetramethyl-8-oxatricyclo[7.2.1.02,7]dodeca-2(7),3,5-triene-4,9,11-triol
• CAS: 359701-26-1
• 化学式: C₁₅H₂₀O₄
• 分子量: 264.321
• InChiKey: DHKFEYFQGRWJNR-VHDGCEQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  enokipodin C 在 18-冠醚-6 、 potassium carbonate 、 4-吡咯烷基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 氯仿 、 乙腈 为溶剂， 反应 16.0h， 生成 3,5-Dichloro-2-(2-methoxy-naphthalen-1-yl)-benzoic acid (1R,2R)-2-(2,5-dimethoxy-4-methyl-phenyl)-2,3,3-trimethyl-4-oxo-cyclopentyl ester
  参考文献：
  名称：

  Antimicrobial Cuparene-Type Sesquiterpenes, Enokipodins C and D, from a Mycelial Culture of Flammulina velutipes

  摘要：

  Two new cuparene-type sesquiterpenes, enokipodins C (1) and D (2), were isolated from culture medium of an edible mushroom, Flammulina velutipes, along with enokipodins A (3) and B (4). The structures of 1 and 2 were determined using spectroscopic methods (HRMS, H-1 and C-13, and 2D NMR). The absolute configuration of enokipodin C was determined from the observed IH NMR chemical shifts and NOEs in NOESY experiments after conversion into the corresponding esters with the chiral reagent 2-(2'-methoxy-1'-naphthyl)-3,4-dichlorobenzoic acid. All the metabolites showed antimicrobial activity against a fungus, Cladosporium herbarum, and Gram-positive bacteria, Bacillus subtilis and Staphylococcus aureus.

  DOI：

  10.1021/np000593r
• 作为产物：
  描述：

  (1S,4R,5S)-4-(2,5-dimethoxy-4-methylphenyl)-3,3,4-trimethyl-6-oxa-bicyclo[3.1.0]hexan-2-one 在 sodium tetrahydroborate 、 sodium dithionite 、 ammonium cerium(IV) nitrate 、 二苯基二硒醚 作用下， 以 乙醇 、 水 、 溶剂黄146 、 乙腈 为溶剂， 反应 2.0h， 生成 enokipodin C
  参考文献：
  名称：

  烯基鬼臼素A–D的对映选择性全合成

  摘要：

  利用Meyers的非对映选择性烷基化方案构建C7季不对称中心，完成了首个对映体全合成的烯基鬼臼草碱A–D，高度氧化的具有抗微生物活性的α-cuparenone型倍半萜。本合成也构成（正式对映选择性合成小号）-1,4- cuparenediol和（小号）-cuparene-1,4-醌。

  DOI：

  10.1016/j.tetlet.2004.04.191

文献信息

• Enantioselective total synthesis of enokipodins A–D
  作者：Shigefumi Kuwahara、Mana Saito

  DOI：10.1016/j.tetlet.2004.04.191

  日期：2004.6

  The first enantioselective total synthesis of enokipodins A–D, highly oxidized α-cuparenone-type sesquiterpenoids with antimicrobial activity, was accomplished by using Meyers' diastereoselective alkylation protocol for the construction of the C7-quaternary asymmetric center. The present synthesis also constitutes a formal enantioselective synthesis of (S)-1,4-cuparenediol and (S)-cuparene-1,4-quinone

  利用Meyers的非对映选择性烷基化方案构建C7季不对称中心，完成了首个对映体全合成的烯基鬼臼草碱A–D，高度氧化的具有抗微生物活性的α-cuparenone型倍半萜。本合成也构成（正式对映选择性合成小号）-1,4- cuparenediol和（小号）-cuparene-1,4-醌。
• POSITIVE ALLOSTERIC MODULATORS OF SWEET TASTE
  申请人：Sensorygen, Inc.

  公开号：US20180132516A1

  公开（公告）日：2018-05-17

  The invention provides natural allosteric modulators that are useful as sweet flavor enhancers. The present invention also includes ingestible compositions comprising the present compounds and methods of enhancing the sweet taste of sweeteners and sugars.
• Enantioselective Total Synthesis of Enokipodins A–D, Antimicrobial Sesquiterpenes Produced by the Mushroom, <i>Flammulina velutipes</i>
  作者：Mana SAITO、Shigefumi KUWAHARA

  DOI：10.1271/bbb.69.374

  日期：2005.1.1

  first enantioselective total synthesis of enokipodins A, B, C and D, highly oxidized alpha-cuparenone-type sesquiterpenoids possessing antimicrobial activity, was accomplished in 8-28% overall yields from methyl (2,5-dimethoxy-4-methylphenyl)acetate by applying Meyers' diastereoselective alkylation protocol for the construction of their C7-quaternary asymmetric center. The present synthesis confirmed

  （2,5-二甲氧基-4-甲基苯基）乙酸甲酯的总收率为8-28％，首次完成了对烯基足蛋白A，B，C和D的对映选择性全合成，这是一种具有抗微生物活性的高度氧化的α-cuparenone型倍半萜。通过应用Meyers的非对映选择性烷基化方案构建其C7-季不对称中心。本合成法证实了烯基鬼臼肽的绝对构型，并且还构成了（S）-1，4-异丙基二醇和（S）-Cuparene-1，4-醌的形式对映选择性合成。
• Antimicrobial Cuparene-Type Sesquiterpenes, Enokipodins C and D, from a Mycelial Culture of <i>Flammulina </i><i>v</i><i>elutipes</i>
  作者：Noemia Kazue Ishikawa、Yukiharu Fukushi、Keiko Yamaji、Satoshi Tahara、Kunihide Takahashi

  DOI：10.1021/np000593r

  日期：2001.7.1

  Two new cuparene-type sesquiterpenes, enokipodins C (1) and D (2), were isolated from culture medium of an edible mushroom, Flammulina velutipes, along with enokipodins A (3) and B (4). The structures of 1 and 2 were determined using spectroscopic methods (HRMS, H-1 and C-13, and 2D NMR). The absolute configuration of enokipodin C was determined from the observed IH NMR chemical shifts and NOEs in NOESY experiments after conversion into the corresponding esters with the chiral reagent 2-(2'-methoxy-1'-naphthyl)-3,4-dichlorobenzoic acid. All the metabolites showed antimicrobial activity against a fungus, Cladosporium herbarum, and Gram-positive bacteria, Bacillus subtilis and Staphylococcus aureus.