(2S,3S,7S)-3,7-dimethyl-2-tridecanol | 141622-90-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S,3S,7S)-3,7-dimethyl-2-tridecanol
• 英文别名: 3S,7S-dimethyl-2S-tridecanol；(2S,3S,7S)-3,7-dimethyltridecan-2-ol
• CAS: 141622-90-4
• 化学式: C₁₅H₃₂O
• 分子量: 228.418
• InChiKey: GSOHTXXXDWFCAJ-KKUMJFAQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  16
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  (2S,3S,7S)-3,7-dimethyl-2-tridecanol 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 生成 (2R,3S,7S)-3,7-dimethyl-2-tridecanol
  参考文献：
  名称：

  Sex pheromone of the pine sawflyDiprion pini (Hymenoptera: Diprionidae): Chemical identification, synthesis and biological activity

  摘要：

  The main component of the sex pheromone secretion of female Diprion pini L. (Hymenoptera: Diprionidae) from insects collected both in Finland and in France has been identified as a threo-3,7-dimethyl-2-tridecanol (8 ng per female) stereoisomer by GC-MS and synthesis. The secretion also contains lower and higher homologues in small amounts (1-4% of the main component). Combined gas chromatographic-electroantennographic detection showed activity in both natural and esterified extracts (acetates and propionates); the esters of the main component gave the largest responses. The acetates and propionates of the eight stereoisomers of 3,7-dimethyl-2-tridecanol were synthesized from enantiomerically highly enriched (> 99% ee) building blocks. The stereochemistry of the main component was established to be (2S,3R,7R) -3,7-dimethyl-2-tridecanol by GC analysis of the natural material. It was purified by liquid chromatography prior to the GC analysis of both its pentafluorobenzoates and its isopropylcarbamates on a nonchiral polar column (ECD) and a chiral column (NPD), respectively. Field tests demonstrated that both the acetate and propionate of the main component (100 mu g of each applied on cotton roll dispensers) were active in attracting males, with or without the presence of several of the minor compounds. Experiments with smaller amounts of the acetate and the propionate (1 mu g in France and 50 mu g in Finland) demonstrated that the propionate was more active than the acetate, and that it also caught more males than a blend of the two compounds.

  DOI：

  10.1007/bf01928898
• 作为产物：
  描述：

  (2S)-2-methyloctan-1-ol 在 吡啶 、 氢氧化钾 、 lithium (3 percent sodium) 、 lithium bromide 、 肼 作用下， 以 丙酮 、 二乙二醇 为溶剂， 反应 7.0h， 生成 (2S,3S,7S)-3,7-dimethyl-2-tridecanol
  参考文献：
  名称：

  松锯齿的性信息素。分离自新双pr虫的一些活性次要成分的手性合成和乙酸二吡啶酯的一些手性类似物的手性合成。

  摘要：

  一些类似物的手性合成，2 - 7，3,7-二甲基-2-十五烷醇，的1（diprionol），以及相应的乙酸酯的描述。1的乙酸盐是Neodiprion属（Diprionidae）的性信息素中的主要引诱剂。化合物2/2-4被鉴定为分离自新双孢虫雌性雌性的次要成分。从手性起始原料，要么制备的合成中间体，通过不对称合成，或通过面包酵母减少。

  DOI：

  10.1016/s0040-4020(01)92255-0

文献信息

• Asymmetric Syntheses of the Sex Pheromones of Pine Sawflies, Their Homologs and Stereoisomers
  作者：Jian-Feng Zheng、Hong-Qiao Lan、Rui-Feng Yang、Qi-Long Peng、Zhen-Hua Xiao、Shi-Chuan Tuo、Kong-Zhen Hu、Yong-Gang Xiang、Zhen Wei、Zhen Zhang、Pei-Qiang Huang

  DOI：10.1002/hlca.201200341

  日期：2012.10

  We describe efficient and flexible enantioselective syntheses of the active enantiomers of the pheromones of pine sawflies, including the species Diprion jingyuanensis, their homologs and, stereoisomers, as well as those identified from the Chinese species Diprion jingyuanensis, i.e., 126. A total of 48 compounds, including acetates 78–101 and propanoates 102–125, have been synthesized. Our general

  我们描述松叶蜂，包括物种的信息素的活性对映体的高效，灵活的对映选择性合成靖远松叶蜂，及其同系物和立体异构体，以及那些从中国物种已查明，靖远松叶蜂，即，126。共有48组的化合物，包括乙酸盐78 - 101和丙酸酯102 - 125，已被合成。我们对这些化合物的一般方法来自于市售的Chirons二乙基（S）-和（R）-苹果酸酯，以及（R）-3-羟基丁酸乙酯。该泽巴赫 在关键步骤中采用不对称甲基化来控制其他构型。
• Sex pheromone of the pine sawflyDiprion pini (Hymenoptera: Diprionidae): Chemical identification, synthesis and biological activity
  作者：G. Bergström、A. -B. Wassgren、O. Anderbrant、J. Fägerhag、H. Edlund、E. Hedenström、H. -E. Högberg、C. Geri、M. A. Auger、M. Varama、B. S. Hansson、J. Löfqvist

  DOI：10.1007/bf01928898

  日期：1995.4

  The main component of the sex pheromone secretion of female Diprion pini L. (Hymenoptera: Diprionidae) from insects collected both in Finland and in France has been identified as a threo-3,7-dimethyl-2-tridecanol (8 ng per female) stereoisomer by GC-MS and synthesis. The secretion also contains lower and higher homologues in small amounts (1-4% of the main component). Combined gas chromatographic-electroantennographic detection showed activity in both natural and esterified extracts (acetates and propionates); the esters of the main component gave the largest responses. The acetates and propionates of the eight stereoisomers of 3,7-dimethyl-2-tridecanol were synthesized from enantiomerically highly enriched (> 99% ee) building blocks. The stereochemistry of the main component was established to be (2S,3R,7R) -3,7-dimethyl-2-tridecanol by GC analysis of the natural material. It was purified by liquid chromatography prior to the GC analysis of both its pentafluorobenzoates and its isopropylcarbamates on a nonchiral polar column (ECD) and a chiral column (NPD), respectively. Field tests demonstrated that both the acetate and propionate of the main component (100 mu g of each applied on cotton roll dispensers) were active in attracting males, with or without the presence of several of the minor compounds. Experiments with smaller amounts of the acetate and the propionate (1 mu g in France and 50 mu g in Finland) demonstrated that the propionate was more active than the acetate, and that it also caught more males than a blend of the two compounds.
• Sex Pheromone of pine sawflies. Chiral syntheses of some active minor components isolated from neodiprion sertifer and of some chiral analogues of diprionyl acetate.
  作者：Erik Hedenström、Hans-Erik Högberg、Ann-Britt Wassgren、Gunnar Bergström、Jan Löfqvist、Bill Hansson、Olle Anderbrant

  DOI：10.1016/s0040-4020(01)92255-0

  日期：1992.4

  some analogues, 2 – 7, of 3,7-dimethyl-2-pentadecanol, 1 (diprionol), and of the corresponding acetates are described. The acetate of 1 is the main attractant in the sex pheromone of the Neodiprion genus (Diprionidae). Compounds 2 /2- 4 were identified as minor components isolated from females of Neodiprion sertifer. Synthetic intermediates were prepared either from chiral starting materials, via asymmetric

  一些类似物的手性合成，2 - 7，3,7-二甲基-2-十五烷醇，的1（diprionol），以及相应的乙酸酯的描述。1的乙酸盐是Neodiprion属（Diprionidae）的性信息素中的主要引诱剂。化合物2/2-4被鉴定为分离自新双孢虫雌性雌性的次要成分。从手性起始原料，要么制备的合成中间体，通过不对称合成，或通过面包酵母减少。