(2E,6Z)-3,7-dimethyl-2,6-nonadien-1-ol | 55546-66-2

• 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: (2E,6Z)-3,7-dimethyl-2,6-nonadien-1-ol
• 英文别名: 2(E),6(Z)-3,7-dimethylnona-2,6-dien-1-ol；Z-homogeraniol；3,7-dimethylnona-2E,6Z-dien-1-ol；(Z)-6-homogeraniol；Zeuwczmrckeceg-yanfreposa-；(2E,6Z)-3,7-dimethylnona-2,6-dien-1-ol
• CAS: 55546-66-2
• 化学式: C₁₁H₂₀O
• 分子量: 168.279
• InChiKey: ZEUWCZMRCKECEG-YANFREPOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 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：

  (2E,6Z)-3,7-dimethyl-2,6-nonadien-1-ol 在 三溴化磷 作用下， 以 乙醚 为溶剂， 生成 3(S),4(S)-faranal
  参考文献：
  名称：

  合成（+）-呋喃醛的便捷途径；法老的蚂蚁的踪迹信息素

  摘要：

  （+）-Faranal是法老王蚂蚁的尾信息素，从易于获得的手性构件开始，并采用非对映选择性碳-碳键形成，以10％的总产率合成。

  DOI：

  10.1016/s0040-4039(00)85322-8
• 作为产物：
  描述：

  (E)-6-((tert-butyldiphenylsilyl)oxy-4methylhex-4-enal) 在 Wilkinson's catalyst manganese(IV) oxide 、 18-冠醚-6 、 四丁基氟化铵 、 氢气 、 双(三甲基硅烷基)氨基钾 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 、 苯 为溶剂， -78.0~25.0 ℃ 、101.33 kPa 条件下， 反应 4.0h， 生成 (2E,6Z)-3,7-dimethyl-2,6-nonadien-1-ol
  参考文献：
  名称：

  Natural and Unnatural Terpenoid Precursors of Insect Juvenile Hormone

  摘要：

  The biosynthesis of insect juvenile hormone (JH) is due, in part, to the precise head-to-tail coupling of allylic and homoallylic diphosphate substrates, as catalyzed by one or more prenyltransferases. To better understand this enzyme's role in JH production, homodimethylallyl diphosphate and both the natural and unnatural homologs of geranyl diphosphate have been prepared as potential substrates for insect prenyltransferase. These latter materials were constructed in a convergent manner by olefination of the corresponding trisnoraldehydes obtained from either terminal oxidative cleavage of geraniol or higher-order cuprate conjugate addition to acrolein. To aid in characterizing the nature of the terpenoid skeletons formed from our in vitro studies, homologous derivatives of farnesol were also prepared by anion coupling of the geranyl derivatives to either C-5 or C-6 allylic bromides. The preparation of these materials and the results of incubations with larval corpora allata homogenates of the lepidopteran Manduca sexta are described.

  DOI：

  10.1021/jo962008q

文献信息

• THE STEREOSPECIFIC PREPARATION OF METHYL FARNESOATE AND SYNTHETIC PRECURSORS OF C₁₈- AND C₁₇JUVENILE HORMONES
  作者：Susumu Kobayashi、Teruaki Mukaiyama

  DOI：10.1246/cl.1974.1425

  日期：1974.12.5

  The new method for the stereospecific preparation of 1,5-diene units was successfully applied to the syntheses of methyl farnesoate and the synthetic precursors of C18- and C17 juvenile hormones, 15 and 20.

  这种新方法成功地用于立体特异性制备1,5-二烯单元，应用于合成甲基法尼酸酯以及C18和C17幼虫激素的合成前体15和20。
• Convenient synthetic route to (+)-faranal and (+)-13-norfaranal
  作者：László Poppe、Lajos Novák、Pál Kolonits、Árpád Bata、Csaba Szántay

  DOI：10.1016/s0040-4020(01)85927-5

  日期：1988.1

  (+)-Faranal 1a, the trail pheromone of Pharaoh's ant, and its congener, (+)-13-norfaranal 1b were synthetized from chiral building block 4 employing diastereoselective carbon-carbon bond formation. The application of crude pig liver esterase enzyme for the preparation of 4 is also discussed.

  （+）-Faranal 1a，法老王蚁的尾部信息素及其同类物（+）-13-norfaranal 1b是由非对映选择性碳-碳键形成的手性结构单元4合成的。还讨论了粗猪肝酯酶在制备4中的应用。
• Regio- and Stereoselective Allylic Substitutions of Chiral Secondary Alkylcopper Reagents: Total Synthesis of (+)-Lasiol, (+)-13-Norfaranal, and (+)-Faranal
  作者：Juri Skotnitzki、Lukas Spessert、Paul Knochel

  DOI：10.1002/anie.201811330

  日期：2019.1.28

  reagents were prepared from chiral secondary alkyl iodides by a retentive I/Li exchange followed by a retentive transmetalation with CuBr⋅P(OEt)3. Switching the solvent to THF significantly increased their configurational stability and made these copper reagents suitable for regioselective allylic substitutions. The optically enriched copper species underwent SN2 substitutions with allylic bromides (up to

  由手性仲烷基碘化物通过保留性I / Li交换，然后用CuBr⋅P（OEt）3进行保留性重金属化，制备了手性仲烷基铜试剂。将溶剂转换为THF可显着提高其构型稳定性，并使这些铜试剂适合于区域选择性的烯丙基取代。光学富集的铜物质经过烯丙基溴的S N 2取代（最高> 99％S N 2区域选择性）。ZnCl 2的添加和手性烯丙基磷酸酯的使用允许将区域选择性转向S N 2'取代（高达> 99％S N 2'区域选择性）并执行高度选择性的抗-S N 2'替换，具有对两个相邻立体中心的绝对控制。该方法用于三种蚂蚁信息素（+）-紫杉醇，（+）-13-正法烷醛和（+）-法烷醛的合成（最高98：2 dr，99％ee）。
• [EN] (S,Z)-3,7-DIMETHYLNON-6-EN-1-OL AND ITS USE AS FRAGRANCE<br/>[FR] (S,Z)-3,7-DIMÉTHYLNON-6-ÉN-1-OL ET SON UTILISATION COMME PARFUM
  申请人：GIVAUDAN SA

  公开号：WO2021198525A1

  公开（公告）日：2021-10-07

  A compound according to formula (IIa), which is (S,Z)-3,7-dimethylnon-6-en-1-ol Formula (IIa), and its use as fragrance.

  一种化合物，其化学式为（IIa），即（S,Z）-3,7-二甲基壬-6-烯-1-醇（式子如下），并且其用途为香料。
• Stereospecific trans-C5-homologization of the isoprenoid chain
  作者：E. V. Polunin、A. M. Moiseenkov

  DOI：10.1007/bf00954349

  日期：1983.7