(S,E)-2,6-dimethyloct-2-en-1,8-diol | 82467-71-8

• 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: (S,E)-2,6-dimethyloct-2-en-1,8-diol
• 英文别名: (4S)-(-)-10-hydroxy-citronellol；(S)-(-)-10-hydroxycitronellol；(E)-8-hydroxycitronellol；(E,6S)-2,6-dimethyloct-2-ene-1,8-diol
• CAS: 82467-71-8
• 化学式: C₁₀H₂₀O₂
• 分子量: 172.268
• InChiKey: FZBXHGXRUNRMTQ-UMYFRRCYSA-N

物化性质

• 沸点：
  275.6±28.0 °C(Predicted)
• 密度：
  0.944±0.06 g/cm3(Predicted)

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：

  (S,E)-2,6-dimethyloct-2-en-1,8-diol 在 N-甲基咪唑 、 4-二甲氨基吡啶 、 2,2'-联吡啶 、 四(三苯基膦)钯 、 2,2,6,6-四甲基哌啶氧化物 、 氧气 、 氯丙烯镁 、 三乙胺 、 sodium hydroxide 、 zinc(II) chloride 、 [Cu(MeCN)₄](OTf) 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 48.5h， 生成 (R)-2-((S,E)-6-methylhepta-4,6-dien-2-yl)oxirane
  参考文献：
  名称：

  A Formal, One-Pot β-Chlorination of Primary Alcohols and Its Utilization in the Transformation of Terpene Feedstock and the Synthesis of a C₂-Symmetrical Terminal Bis-Epoxide

  摘要：

  A one-pot transformation of alkan-1-ols into 2-chloroalkan-1-ols is described. As a practical application, terpene-derived primary alcohols were converted into semiochemicals such as olfactory lactones (aerangis lactone, whisky lactone, and cognac lactone) and pheromones (cruentol and ferrugineol). Using heptane-1,7-diol as a bifunctional substrate, the corresponding bis-epoxide was synthesized by bidirectional synthesis in good yield and high enantioselectivity.

  DOI：

  10.1021/jo402422b
• 作为产物：
  描述：

  (S)-(-)-β-香茅醇 在 吡啶 、 aluminium hydride 、 ozone-containing oxygen 、 锌 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 (S,E)-2,6-dimethyloct-2-en-1,8-diol
  参考文献：
  名称：

  Studies on monoterpene glucosides and related natural products. XLV. Synthesis of 13C-labeled acyclic monoterpenes for studies on the mechanism of the iridane skeleton formation in the biosynthesis of iridoid glucosides.

  摘要：

  在研究从无环单萜生成环戊烷环的生物合成途径中，我们合成了以下13C标记的无环单萜系列前体:[9-13C]-和[4-13C]-10-羟基香茅醇(9)、[2-13C]-9, 10-二羟基香茅醇(10)、(R)-(+)-和(S)-(-)-[9-13C]-10-羟基香茅醇((R)-(+)-和(S)-(-)-8)、(R)-(+)-和(S)-(-)-[8-13C]-9, 10-二羟基香茅醇((R)-(+)-和(S)-(-)-11)。

  DOI：

  10.1248/cpb.30.927

文献信息

• Hydroxylation of benzylic and allylic sites by plant cultured suspension cells
  作者：Hiroki Hamada、Toshinori Tanaka、Tsutomu Furuya、Hiroki Takahata、Hideo Nemoto

  DOI：10.1016/s0040-4039(00)02132-8

  日期：2001.1

  A novel transformation of α-substituted benzylcyanides by hydroxylation of benzyl sites using cultured cells of cotton, Gossypium hirsutum, producing alkano- or benzophenones via presumably α-cyanohydrin is demonstrated. Also regioselective hydroxylation of 4S-(−)-perillyl alcohol and 3S-(−)-citronellol by cultured suspension cells of Catharanthus roseus is reported.

  证明了使用棉花的棉花细胞培养的细胞通过苄基位的羟基化对α-取代的苄基氰的新型转化，其推测通过α-氰醇产生链烷酮或二苯甲酮。还报道了由长春花培养的悬浮细胞对4 S -（-）-紫苏醇和3 S -（-）-香茅醇的区域选择性羟基化。
• Synthetic studies of the HIV-1 protease inhibitive didemnaketals: stereocontrolled synthesis of an ester side chain
  作者：Xue Zhi Zhao、Yong Qiang Tu、Lei Peng、Xue Qiang Li、Yan Xing Jia

  DOI：10.1016/j.tetlet.2004.03.103

  日期：2004.5

  The stereocontrolled synthesis of the C1–C8 portion, the ester side chain of the HIV-1 protease inhibitive didemnaketals from the ascidian Didemnum sp., has been carried out through 15 steps starting from (S)-carvone as the chiral template. This approach involved the diastereoselective construction of three conjoint chiral centers by intramolecular chiral inducement, and generation of allylic alcohol

  C 1 – C 8部分（来自海鞘Didemnum sp。的HIV-1蛋白酶抑制性二苯乙酮的酯侧链）的立体控制合成已从（S）-香芹酮为手性模板开始，经过15个步骤进行。该方法涉及通过分子内手性诱导的三个联合手性中心的非对映选择性构建，以及通过关键的Grob断裂反应产生烯丙醇中间体。
• The aphid sex pheromone cyclopentanoids: Synthesis in the elucidation of structure and biosynthetic pathways
  作者：Glenn W. Dawson、John A. Pickett、Diane W.M. Smiley

  DOI：10.1016/0968-0896(96)00012-0

  日期：1996.3

  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