<2S-(2α(7R^*,8R^*),3aα,4β,7β,7aα)>-2-Methyl-8-<(octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl)oxy>octadecan-7-ol | 132881-30-2

• 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: <2S-(2α(7R^*,8R^*),3aα,4β,7β,7aα)>-2-Methyl-8-<(octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl)oxy>octadecan-7-ol
• 英文别名: <2S-(2a(7R*,8R*),3aα,4β,7β,7aα)>-2-methyl-8-<(octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl)oxy>octadecan-7-ol；(7S,8S)-2-methyl-8-[[(1R,2R,4S,6R,7R)-1,10,10-trimethyl-3-oxatricyclo[5.2.1.02,6]decan-4-yl]oxy]octadecan-7-ol
• CAS: 132881-30-2
• 化学式: C₃₁H₅₈O₃
• 分子量: 478.8
• InChiKey: OQMCHYLCFBYVHC-CXJQJBEQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.7
• 重原子数：
  34
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  <2S-(2α(7R^*,8R^*),3aα,4β,7β,7aα)>-2-Methyl-8-<(octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl)oxy>octadecan-7-ol 在 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 反应 21.25h， 生成 <2S-(2α,3aα,4β,7β,7aα)>-2-Methoxy-
  参考文献：
  名称：

  Pheromone, 1. Mitt.: (+)-cis-Disparlure: Synthese und Feldtests

  摘要：

  A synthesis of (+)-cis-disparlure is described starting from racemic 2-hydroxy-dodecan-nitrile (2), which is transformed into the O-protected enantiomerically pure cyanohydrine 4. Grignard-reaction followed by reduction with BH3.(CH3)2S yields the corresponding threo-configurated secondary alcohol 10. After tosylation and cleavage of the MBE-protective-group (+)-cis-disparlure (14) is obtained by treatment with KOH. Mating disruption field tests exhibited a significantly increased effectiveness of (+)-cis-disparlure as compared to the racemic product.

  DOI：

  10.1007/bf00815171
• 作为产物：
  描述：

  <2S-(2α(R^*),3aα,4β,7β,7aα)>-2-Methyl-8-<(octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl)oxy>octadecan-7-on 在 dimethyl sulfide borane 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 <2S-(2α(7S^*,8R^*),3aα,4β,7β,7aα)>-2-Methyl-8-<(octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl)oxy>octadecan-7-ol 、 <2S-(2α(7R^*,8R^*),3aα,4β,7β,7aα)>-2-Methyl-8-<(octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl)oxy>octadecan-7-ol
  参考文献：
  名称：

  Pheromone, 1. Mitt.: (+)-cis-Disparlure: Synthese und Feldtests

  摘要：

  A synthesis of (+)-cis-disparlure is described starting from racemic 2-hydroxy-dodecan-nitrile (2), which is transformed into the O-protected enantiomerically pure cyanohydrine 4. Grignard-reaction followed by reduction with BH3.(CH3)2S yields the corresponding threo-configurated secondary alcohol 10. After tosylation and cleavage of the MBE-protective-group (+)-cis-disparlure (14) is obtained by treatment with KOH. Mating disruption field tests exhibited a significantly increased effectiveness of (+)-cis-disparlure as compared to the racemic product.

  DOI：

  10.1007/bf00815171

文献信息

• Pheromone, 3.Mitt.: Eine einfache Methode zur Steuerung der Reduktion von ?-Alkoxy-carbonylverbindungen
  作者：Christian R. Noe、M. Knollm�ller、G. Steinbauer、E. Wagner、H. K�rner、P. Ettmayer、H. V�llenkle

  DOI：10.1007/bf00810831

  日期：1991.4

  Enantiomerically pure 1,2-diols bearing optionally syn or anti configurated secondary hydroxylic groups are synthesized from acetal-protected cyanohydrins. After resolution of the diastereomers the cyanohydrins are converted into alpha-alkoxy-ketones by Grignard-reaction followed by reduction using common chelating or non-chelating agents. Among others syntheses of enantiomerically pure pheromones, endo-Brevicomin, exo-Brevicomin and Dispalure are given as examples.
• Pheromone, 1. Mitt.: (+)-cis-Disparlure: Synthese und Feldtests
  作者：Christian R. Noe、Max Knollm�ller、Helmut K�rner、Gerhard Steinbauer、Helmut Koberg、Peter G�rtner

  DOI：10.1007/bf00815171

  日期：——

  A synthesis of (+)-cis-disparlure is described starting from racemic 2-hydroxy-dodecan-nitrile (2), which is transformed into the O-protected enantiomerically pure cyanohydrine 4. Grignard-reaction followed by reduction with BH3.(CH3)2S yields the corresponding threo-configurated secondary alcohol 10. After tosylation and cleavage of the MBE-protective-group (+)-cis-disparlure (14) is obtained by treatment with KOH. Mating disruption field tests exhibited a significantly increased effectiveness of (+)-cis-disparlure as compared to the racemic product.