intermedeol | 6168-59-8

• 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: intermedeol
• 英文别名: (1S,4aS,7R,8aS)-1,4a-dimethyl-7-prop-1-en-2-yl-2,3,4,5,6,7,8,8a-octahydronaphthalen-1-ol
• CAS: 6168-59-8
• 化学式: C₁₅H₂₆O
• 分子量: 222.371
• InChiKey: DPQYOKVMVCQHMY-QPSCCSFWSA-N

物化性质

• 熔点：
  47-48 °C
• 沸点：
  298.5±19.0 °C(Predicted)
• 密度：
  0.949±0.06 g/cm3(Predicted)
• 保留指数：
  1626

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  intermedeol 生成 selin-11-en-4α-ol
  参考文献：
  名称：

  来自红花的 Eudesmane 苷

  摘要：

  摘要 从红花正己烷提取物中分离得到两种新的eudesmane 苷，intermedeol β-d-fupyranoside 及其2' α-methylbutyrate，并通过光谱和化学方法建立了它们的结构。

  DOI：

  10.1016/0031-9422(90)80186-k
• 作为产物：
  描述：

  法呢基焦磷酸盐三铵盐 在 (+)-intermedeol synthase 、 水 作用下， 以 aq. buffer 为溶剂， 生成 intermedeol
  参考文献：
  名称：

  白蚁相关真菌Termmitomyces的三种倍半萜烯合酶的机械表征

  摘要：

  来自白蚁相关真菌Termmitomyces的三个萜烯合酶在功能上被表征为（+）-间苯二酚合酶，（-）-γ-卡丹烯合酶和（+）-germacrene D-4-ol合酶以及胚芽烯D-4-ol合酶作为第一个报道的产生（+）-对映体的酶。通过与同位素标记的前体孵育来彻底研究酶促机制，以遵循催化中单个反应步骤的立体化学过程。通过在所有三种酶中的高度保守的色氨酸进行定点诱变以及通过同源性模型分析确定的（-）-γ-in二烯合酶中的其他残基，对假定的活性位点残基的作用进行了测试。

  DOI：

  10.1039/c8ob02744g

文献信息

• COMPOUNDS AND METHODS FOR REPELLING BLOOD-FEEDING ARTHROPODS AND DETERRING THEIR LANDING AND FEEDING
  申请人：Gries Regine M

  公开号：US20110251270A1

  公开（公告）日：2011-10-13

  This invention relates to a group of compounds for repelling blood-feeding ectoparasitic arthropods, and a method of deterring their landing and feeding on animals including humans, by applying in one or more formulations compounds that incorporate one or more sulfide and one or more hydroxyl groups to the skin, clothing or environment of animals, including humans. A method of repelling and deterring landing and feeding by blood-feeding arthropods on an animal by applying in effective amount one or more compounds that incorporate alkyl sulfide and alcohol moieties, or alkyl sulfide and amide moieties, or alkyl sulfide and amide moieties to the skin, clothing or environment of an animal.

  本发明涉及一类化合物，用于驱避吸血性外寄生节肢动物，并通过将含有一种或多种硫化物和一种或多种羟基的化合物应用于动物（包括人类）的皮肤、衣服或环境中的一种或多种制剂来防止它们降落和吸血。本发明还涉及一种通过在动物的皮肤、衣服或环境中应用一种或多种含有烷基硫醇和醇基或烷基硫醇和酰胺基或烷基硫醇和酰胺基的化合物的有效量来驱避和防止血吸虫降落和吸血的方法。
• Novel clerodanes and methods for repelling arthropods
  申请人：Cantrell L. Charles

  公开号：US20060235071A1

  公开（公告）日：2006-10-19

  A method for repelling arthropods involving treating a subject or an object with an arthropod repelling composition containing an arthropod repelling effective amount of at least one clerodane of the formula in which R 1 is H, halogen, formyl, a straight chain or branched C 1-4 saturated alkyl, a straight chain or branched C 2-4 unsaturated alkyl, or an aryl containing 6-10 carbon atoms in the ring skeleton thereof, wherein R 1 is unsubstituted or substituted with one or more substituents, which are the same or different, selected from the group consisting of oxo (═O), OR 2 , CO 2 R 2 , and OC(O)R 2 , wherein R 2 is H, a straight chain or branched C 1-30 saturated alkyl, a straight chain or branched C 2-30 unsaturated alkyl, or an aryl comprising 6-10 carbon atoms in the ring skeleton thereof; wherein R 2 is unsubstituted or substituted with one or more substituents selected from the group consisting of halogen, amino, hydroxyl, oxo (═O), thio, cyano and nitro; optionally a carrier, optionally an arthropod repellant, and optionally an insecticide. Preferably the compound is 13,14,15,16-tetranorclerod-3-en-12-al (callicarpenal), 13,14,15,16-tetranorclerod-3-en-12-ol, 13,14,15,16-tetranorclerod-3-en-12-oic acid, β-epoxycallicarpenal, α-epoxycallicarpenal, or mixtures thereof. Also a compound of the above formula. Also an arthropod repellant composition containing an arthropod repelling effective amount of at least one of the compounds of the above formula and a carrier.

  一种驱避节肢动物的方法，涉及使用含有至少一种公式中的至少一种克氏二烯的节肢动物驱避剂组成物来处理主体或物体，其中R1为H、卤素、甲酰基、直链或支链C1-4饱和烷基、直链或支链C2-4不饱和烷基或其苯环骨架中含有6-10个碳原子的芳基，其中R1未被取代或被取代一个或多个取代基，所述取代基相同或不同，选自氧代（═O）、OR2、CO2R2和OC（O）R2的群，其中R2为H、直链或支链C1-30饱和烷基、直链或支链C2-30不饱和烷基或其苯环骨架中含有6-10个碳原子的芳基；其中R2未被取代或被取代一个或多个取代基，所述取代基选自卤素、氨基、羟基、氧代（═O）、硫代、氰基和硝基的群；可选载体、可选节肢动物驱避剂和可选杀虫剂。优选的化合物是13,14,15,16-四去氢克氏二烯-3-烯-12-醛（卡利卡尔彭醛）、13,14,15,16-四去氢克氏二烯-3-烯-12-醇、13,14,15,16-四去氢克氏二烯-3-烯-12-酸、β-环氧卡利卡尔彭醛、α-环氧卡利卡尔彭醛或其混合物。还包括上述公式的化合物。还包括含有上述公式化合物之一和载体的节肢动物驱避剂组成物。
• Compounds and methods for repelling blood-feeding arthropods and deterring their landing and feeding
  申请人：Scotts Canada Ltd.

  公开号：US10842726B2

  公开（公告）日：2020-11-24

  This invention relates to a group of compounds for repelling blood-feeding ectoparasitic arthropods, and a method of deterring their landing and feeding on animals including humans, by applying in one or more formulations compounds that incorporate one or more sulfide and one or more hydroxyl groups to the skin, clothing or environment of animals, including humans. A method of repelling and deterring landing and feeding by blood-feeding arthropods on an animal by applying in effective amount one or more compounds that incorporate alkyl sulfide and alcohol moieties, or alkyl sulfide and amide moieties, or alkyl sulfide and amide moieties to the skin, clothing or environment of an animal.

  本发明涉及一组用于驱赶吸血外寄生节肢动物的化合物，以及一种通过在一种或多种制剂中将含有一个或多个硫化物和一个或多个羟基的化合物施用到包括人类在内的动物的皮肤、衣物或环境中，阻止其在动物（包括人类）身上着陆和取食的方法。一种通过在动物的皮肤、衣物或环境中施用有效量的一种或多种含有硫化烷基和醇基、或硫化烷基和酰胺基、或硫化烷基和酰胺基的化合物来驱赶和阻止动物身上的食血节肢动物着陆和取食的方法。
• Synthetic approaches to 10-epieudesmane sesquiterpenes. A synthesis of intermedeol
  作者：J. W. Huffman、C. A. Miller、A. R. Pinder

  DOI：10.1021/jo00885a011

  日期：1976.11
• Synthesis of all stereoisomers of eudesm-11-en-4-ol. 2. Total synthesis of selin-11-en-4.alpha.-ol, intermedeol, neointermedeol, and paradisiol. First total synthesis of amiteol
  作者：Ronald P. W. Kesselmans、Joannes B. P. A. Wijnberg、Adriaan J. Minnaard、Robert E. Walinga、Aede De Groot

  DOI：10.1021/jo00026a012

  日期：1991.12

  The syntheses of (+/-)-selin-11-en-4-alpha-ol (5), (+/-)-intermedeol (6), (+/-)-neointermedeol (7), (+/-)-amiteol (9), and the four remaining unnatural stereoisomers (+/-)-paradisiol (8), (+/-)-7-epi-amiteol (10), (+/-)-5-epi-neointermedeol (11), and (+/-)-5-epi-paradisiol (12) are described. In addition, the related (+/-)-evuncifer ether (25) has been prepared. The syntheses started from the octahydro-8-hydroxy-4a,8-dimethyl-2(1H)-naphthalenones 1-4. The reaction sequence employed for the synthesis of 5, 7, 9, and 12 involved Wittig reaction, oxidative hydroboration, oxidation, equilibration, and olefination. For the synthesis of 6, 8, 10, and 11 the interim equilibration step was omitted. The oxidative hydroboration was the key step in these syntheses.