cis-isogeraniol | 5944-20-7

• 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: cis-isogeraniol
• 英文别名: isogeraniol；(Z)-3,7-dimethyl-octa-3,6-dien-1-ol；cis-isogeraniol；seq-cis-1,7-Dimethylocta-3,6-dienol；cis-β-isogeraniol；(3Z)-3,7-dimethylocta-3,6-dien-1-ol
• CAS: 5944-20-7
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: DTHIOPUFUOMHAY-POHAHGRESA-N

物化性质

• 沸点：
  102-103 °C(Press: 9 Torr)
• 密度：
  0.8787 g/cm3
• 溶解度：
  Insoluble in water, soluble in alcohol and oils.
• 保留指数：
  1237
• 稳定性/保质期：
  存在于主流烟气中。

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

制备方法与用途

合成制备方法

1. 由3-亚甲基-1-丁醇制备。

反应信息

• 作为产物：
  描述：

  香叶醇 、 三氧化铬 生成 cis-isogeraniol
  参考文献：
  名称：

  SHOSEYOV, O.;BRAVDO, B. A.;SIEGEL, D.;GOLDMAN, A.;COHEN, S.;IKAN, R., VITIS, 29,(1990) N, C. 159-163

  摘要：

  DOI：

文献信息

• Process for preparing 3-substituted 2-alkenals, in particular prenal
  申请人：BASF SE

  公开号：EP2597081A1

  公开（公告）日：2013-05-29

  The present invention to a process for preparing 2-alkenals of the formula I in which R1 is selected from hydrogen and C1-C4-alkyl; and R2 is selected from hydrogen, C1-C12-alkyl, C2-C12-alkenyl, C4-C8-cycloalkyl and C6-C10-aryl, wherein C1-C12-alkyl and C1-C12-alkenyl may be substituted with C5-C7-cycloalkyl or C5-C7-cylcoalkenyl ; comprising dehydrogenating an alkenol of the formula II, an alkenol of the formula III or a mixture thereof, wherein R1 and R2 are each as defined above, wherein the alkenol II, the alkenol II or a mixture thereof is brought into contact with a catalytic system comprising at least one ligand and a metal compound selected from ruthenium(II) compounds and iridium(I) compounds, and wherein the hydrogen formed during the dehydrogenation is removed from the reaction mixture by: i) reaction with a reoxidant selected from C3-C12-alkanones, C4-C9-cycoalkanones, benzaldehyde and mixtures thereof; and/or ii) purely physical means.

  本发明涉及一种制备式I的2-烯醛的方法，其中R1从氢和C1-C4-烷基中选择；R2从氢、C1-C12-烷基、C2-C12-烯基、C4-C8-环烷基和C6-C10-芳基中选择，其中C1-C12-烷基和C1-C12-烯基可以被C5-C7-环烷基或C5-C7-环烯基取代；包括脱氢式II的烯醇、式III的烯醇或二者的混合物，其中R1和R2如上所定义，其中烯醇II、烯醇II或二者的混合物与至少一种配体和选择自钌(II)化合物和铱(I)化合物的金属化合物组成的催化系统接触，并且在脱氢过程中生成的氢通过以下方法从反应混合物中去除：i) 与选择自C3-C12-酮、C4-C9-环酮、苯甲醛和其混合物的氧化剂反应；和/或ii) 纯物理手段。
• [EN] PROCESS FOR PREPARING 3-SUBSTITUTED 2-ALKENALS, IN PARTICULAR PRENAL<br/>[FR] PROCÉDÉ POUR LA PRÉPARATION DE 2-ALCÉNALS 3-SUBSTITUÉS, EN PARTICULIER DE PRÉNAL
  申请人：BASF SE

  公开号：WO2013076226A1

  公开（公告）日：2013-05-30

  The present invention to a process for preparing 2-alkenals of the formula (I) in which R1 is selected from hydrogen and C1-C4-alkyl; and R2 is selected from hydrogen, C1-C12-alkyl, C2-C12-alkenyl, C4-C8-cycloalkyl and C6-C-10 aryl, wherein C1-C12-alkyl and C1-C12-alkenyl may be substituted with C5-C7-cycloalkyl or C5-C7-cylcoalkenyl; comprising dehydrogenating an alkenol of the formula (II), an alkenol of the formula (III) or a mixture thereof, wherein R1 and R2 are each as defined above, wherein the alkenol II, the alkenol III or a mixture thereof is brought into contact with a catalytic system comprising at least one ligand and a metal compound selected from ruthenium(II) compounds and iridium(I) compounds, and wherein the hydrogen formed during the dehydrogenation is removed from the reaction mixture by: i) reaction with a reoxidant selected from C3-C12-alkanones, C4-C9-cycoalkanones, benzaldehyde and mixtures thereof; and/or ii) purely physical means.

  本发明涉及一种制备式(I)的2-烯醛的方法，其中R1从氢和C1-C4-烷基中选择；R2从氢、C1-C12-烷基、C2-C12-烯基、C4-C8-环烷基和C6-C-10芳基中选择，其中C1-C12-烷基和C1-C12-烯基可以被C5-C7-环烷基或C5-C7-环烯基取代；包括脱氢式(II)的烯醇、式(III)的烯醇或二者的混合物，其中R1和R2如上所定义，其中烯醇II、烯醇III或二者的混合物与至少一种配体和选择自钌(II)化合物和铱(I)化合物的金属化合物组成的催化系统接触，脱氢过程中生成的氢通过以下方法从反应混合物中除去：i) 与选择自C3-C12-酮、C4-C9-环酮、苯甲醛和它们的混合物的氧化剂反应；和/或ii) 纯物理手段。
• On the regioselectivity of elimination reactions in terpene derivatives
  作者：B. Badet、M. Julia、J.M. Mallet、C. Schmitz

  DOI：10.1016/s0040-4020(88)90028-2

  日期：1988.1
• Toward higher polyprenols under ‘prebiotic’ conditions
  作者：Laurent Désaubry、Yoichi Nakatani、Guy Ourisson

  DOI：10.1016/s0040-4039(03)01624-1

  日期：2003.9

  Geraniol and isomers (C-10) can be obtained by the condensation of C-5 monoprenols at room temperature in the presence of montmorillonite K-10. It is also possible to obtain farnesol (C-15) and isomers by condensation of geraniol with isopentenol. Despite the low yields achieved, these findings support the hypothesis that polyprenyl phosphates may have been formed in prebiotic conditions, and served as constituents of primitive membranes. (C) 2003 Elsevier Ltd. All rights reserved.
• MOISEENKOV, A. M.;POLUNIN, E. V., DOKL. AN CCCP, 1982, 263, N 2, 369-371
  作者：MOISEENKOV, A. M.、POLUNIN, E. V.

  DOI：——

  日期：——

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