(E)-2,6-dimethyloct-2-ene-1,8-diol | 26489-18-9

• 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: (E)-2,6-dimethyloct-2-ene-1,8-diol
• 英文别名: (±)-(E)-8-hydroxycitronellol；(+/-)-trans-8-hydroxy-citronellol；2,6-dimethyl-oct-2-ene-1,8-diol；2,6-Dimethyl-oct-2-en-1,8-diol；(e)-2,6-Dimethyl-2-octen-1,8-diol
• CAS: 26489-18-9
• 化学式: C₁₀H₂₀O₂
• 分子量: 172.268
• InChiKey: FZBXHGXRUNRMTQ-BJMVGYQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-2,6-dimethyloct-2-ene-1,8-diol 在 platinum(IV) oxide 、 氢气 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以56%的产率得到2,6-二甲基辛烷-1,8-二醇
  参考文献：
  名称：

  Chiral synthetic intermediates via asymmetric hydrogenation of .alpha.-methyl-.alpha.,.beta.-unsaturated aldehydes by bakers' yeast

  摘要：

  DOI：

  10.1021/jo00223a038
• 作为产物：
  描述：

  乙酸香茅酯 在 叔丁基过氧化氢 、 lithium aluminium tetrahydride 、 selenium(IV) oxide 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 121.0h， 生成 (E)-2,6-dimethyloct-2-ene-1,8-diol
  参考文献：
  名称：

  The aphid sex pheromone cyclopentanoids: Synthesis in the elucidation of structure and biosynthetic pathways

  摘要：

  Identification of a range of aphid sex pheromones as comprising the cyclopentanoids (4aS,7S,7aR)-nepetalactune, (1R,4aS,7S,7aR)-nepetalactol and the (1S)- and (1R,4aR,7S,7aS)-nepetalactols required samples authenticated by H-1 and C-13 NMR. These and related compounds were provided by small scale synthesis and extraction from plants in the genus Nepeta (Lamiaceae). The subsequent discovery that the synthetic sex pheromones could attract males, and also parasitic wasps that attack aphids, has created a need for large scale syntheses of the cyclopentanoids. This is afforded by cyclisation of the 8-oxo-1-enamine of citronellal as originally developed by Schreiber and co-workers (1986). Investigation into the biosynthesis of the cyclopentanoids by plants for exploiting aphid sex pheromones in crop protection by means of molecular biology required synthesis of putative biosynthetic intermediates, some with radioactive isotopic labelling, particularly 8-oxidised monoterpene alcohols and aldehydes. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00012-0

文献信息

• [EN] PROCESS FOR MAKING A CONJUGATED DIENE FROM AN ALLYL ALCOHOL<br/>[FR] PROCÉDÉ DE FABRICATION D'UN DIÈNE CONJUGUÉ À PARTIR D'UN ALCOOL D'ALLYLE
  申请人：GIVAUDAN SA

  公开号：WO2021255052A1

  公开（公告）日：2021-12-23

  An in-situ method for making a conjugated diene from an allyl alcohol comprising the conversion of the allyl alcohol to an allyl carbonate, allyl ester or allyl formate with concomitant or subsequent conversion of the allyl carbonate, allyl ester or allyl formate to the conjugated diene; the products obtained by said method, and the uses of said products.

  一种从烯丙醇制备共轭二烯的原位方法，包括将烯丙醇转化为烯丙碳酸酯、烯丙酯或烯丙甲酸酯，同时或随后将烯丙碳酸酯、烯丙酯或烯丙甲酸酯转化为共轭二烯；所述方法获得的产物以及所述产物的用途。
• Biosynthesis of nepetalactone in Nepeta cataria
  作者：Franco Bellesia、Romano Grandi、Ugo M. Pagnoni、Adriano Pinetti、Roberto Trave

  DOI：10.1016/0031-9422(84)83082-4

  日期：1984.1

  Abstract Iridodial is a key intermediate in the biosynthesis of nepetalactone. One of the steps on the pathway prior to the lactonization is a hydride shift from C-1 to C-10. 10-Hydroxycitronellol is a far more efficient precursor than the C-2/C-3 unsaturated analogue.

  摘要 Iridodial 是荆芥内酯生物合成的关键中间体。内酯化之前途径的步骤之一是从 C-1 到 C-10 的氢化物转变。10-羟基香茅醇是比 C-2/C-3 不饱和类似物更有效的前体。
• Regiospecific hydroxylation of acyclic monoterpene alcohols by aspergillus niger
  作者：K.Madhava Madyastha、N.S.R.Krishna Murthy

  DOI：10.1016/s0040-4039(00)80155-0

  日期：——

  Aspergillus niger was shown to carry out the regiospecific hydroxylation of acyclic monoterpene alcohols.

  显示黑曲霉进行无环单萜醇的区域特异性羟基化。
• Biotransformation of geraniol, nerol and (+)- and (−)-carvone by suspension cultured cells of Catharanthus roseus
  作者：Hiroki Hamada、Hideaki Yasumune、Yoshihiro Fuchikami、Toshifumi Hirata、Isabel Sattler、Howard J. Williams、A. Ian Scott

  DOI：10.1016/s0031-9422(96)00566-3

  日期：1997.2

  Abstract Suspension cultured cells of Catharanthus roseus hydroxylate the allylic positions of geraniol, nerol and (+)- and (−)-carvone and reduce double bonds and ketone groups. After incubation for 7 days, the main products of (−)- and (+)-carvone were 5β-hydroxyneodihydrocarveol and 5α-hydroxycarvone, respectively.

  摘要 长春花悬浮培养细胞使香叶醇、橙花醇和(+)-和(-)-香芹酮的烯丙基位置羟基化并减少双键和酮基。培养7天后，(-)-和(+)-香芹酮的主要产物分别为5β-羟基新二氢香芹酮和5α-羟基香芹酮。
• Biosynthesis of loganin and the indole alkaloids from hydroxygeraniol–hydroxynerol
  作者：A. R. Battersby、S. H. Brown、T. G. Payne

  DOI：10.1039/c29700000827

  日期：——

  Tracer experiments on Vinca rosea indicate that the conversion of geraniol and nerol into loganin and the indole alkaloids involves 10-hydroxylation as the primary step.

  在长春花上的示踪剂实验表明，香叶醇和神经醇转化为loganin和吲哚生物碱涉及的主要步骤是10-羟基化。