(4R,5S)-trans-p-mentha-1,8-dien-5-ol | 890711-66-7

• 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: (4R,5S)-trans-p-mentha-1,8-dien-5-ol
• 英文别名: trans-Δ^1,6,Δ^8,9-p-Menthadien-3-ol；Rel-(1S,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-3-en-1-ol；(1S,6R)-3-methyl-6-prop-1-en-2-ylcyclohex-3-en-1-ol
• CAS: 890711-66-7
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: ZTDBSRAQWPKHIO-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• 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

反应信息

• 作为反应物：
  描述：

  (4R,5S)-trans-p-mentha-1,8-dien-5-ol 在 正丁基锂 、 potassium tert-butylate 、 氟-二甲氧基硼烷 、 双氧水 作用下， 以 正己烷 为溶剂， 以41%的产率得到(1S,6R)-6-[1-(hydroxymethyl)vinyl]-3-methylcyclohex-3-en-1-ol
  参考文献：
  名称：

  New Stereoselective Synthesis of Paeonilactone B

  摘要：

  从对映体富集的萜醇 2 开始，经过 10 个步骤实现了芍药内酯 B 的新立体选择性合成，总产率为 11.5%。关键合成步骤基于区域选择性金属化以及区域和非对映选择性环氧化。

  DOI：

  10.1055/s-0028-1088039
• 作为产物：
  描述：

  (1RS,6RS)-6-acetyl-3-methylcyclohex-3-en-1-yl acetate 在 正丁基锂 、 Burkholderia cepacia PS lipase 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 336005.5h， 生成 (4R,5S)-trans-p-mentha-1,8-dien-5-ol
  参考文献：
  名称：

  Enzyme-mediated preparation of enantioenriched forms of trans- and cis-p-menthan-1,8-dien-5-ol

  摘要：

  The synthesis of the trans-p-menthan-5-ol (+/-)-1 was carried out by Diels-Alder cycloaddition of 3-keto-1-butenyl-acetate 3 with isoprene followed by Wittig methylenation. PS lipase resolution of the alcohol afforded acetate (-)-5 with 98% ec, which was hydrolysed to give (-)1. Alternatively, enzymatic hydrolysis of a keto ester followed by Wittig methylenation and hydrolysis afforded the same alcohol with an ee of 86%. The cis-p-menthan-5-ol (-)-2 was obtained by Swern oxidation of (-)-1. followed by diastereoselective reduction with L-Selectride without lost of enantiomeric excess. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2006.02.012

文献信息

• Composition for plant disease control comprising limonene derivatives as active ingredients
  申请人：KOREA ATOMIC ENERGY RESEARCH INSTITUTE

  公开号：US11213029B2

  公开（公告）日：2022-01-04

  The present invention relates to a composition for controlling plant diseases containing a limonene derivative as an active ingredient. In the present invention, the limonene derivatives have an effect of inhibiting the growth of Xanthomonas oryzae pv. Oryzae (Xoo), which is a pathogen mediating bacterial leaf blight, and Magnaporthe oryzae, which is a pathogen mediating rice blast, and it was confirmed in an experiment with respect to inhibition using volatility (i.e., in a state not being in direct contact with Xoo or M. oryzae) that the limonene derivatives have a growth inhibitory effect. Accordingly, the limonene derivatives have an inhibitory effect against the growth of Xoo and thus they can be effectively used as a composition for controlling plant diseases.

  本发明涉及一种含有柠檬烯衍生物作为活性成分的用于防治植物病害的组合物。在本发明中，柠檬烯衍生物具有抑制黄单胞菌(Xanthomonas oryzae pv. Oryzae，Xoo)和木格氏菌(Magnaporthe oryzae，Magnaporthe oryzae)生长的效果，前者是介导细菌性叶枯病的病原体，后者是介导稻瘟病的病原体，在使用挥发性（即在不与 Xoo 或 M. oryzae 直接接触的状态下）进行的抑制实验中证实，柠檬烯衍生物具有生长抑制效果。因此，柠檬烯衍生物对 Xoo 的生长具有抑制作用，可以有效地用作控制植物病害的成分。
• Enzyme-mediated preparation of enantioenriched forms of trans- and cis-p-menthan-1,8-dien-5-ol
  作者：Elisabetta Brenna、Claudio Fuganti、Francesco G. Gatti、Marco Perego、Stefano Serra

  DOI：10.1016/j.tetasy.2006.02.012

  日期：2006.3

  The synthesis of the trans-p-menthan-5-ol (+/-)-1 was carried out by Diels-Alder cycloaddition of 3-keto-1-butenyl-acetate 3 with isoprene followed by Wittig methylenation. PS lipase resolution of the alcohol afforded acetate (-)-5 with 98% ec, which was hydrolysed to give (-)1. Alternatively, enzymatic hydrolysis of a keto ester followed by Wittig methylenation and hydrolysis afforded the same alcohol with an ee of 86%. The cis-p-menthan-5-ol (-)-2 was obtained by Swern oxidation of (-)-1. followed by diastereoselective reduction with L-Selectride without lost of enantiomeric excess. (c) 2006 Published by Elsevier Ltd.
• New Stereoselective Synthesis of Paeonilactone B
  作者：Francesco Gatti、Stefano Serra

  DOI：10.1055/s-0028-1088039

  日期：2009.4

  A new stereoselective synthesis of paeonilactone B has been achieved in ten steps and in 11.5% overall yield starting from the enantiomerically enriched terpenol 2. Key synthetic steps are based on a regioselective metalation and on a regio- and diastereoselective epoxidation.

  从对映体富集的萜醇 2 开始，经过 10 个步骤实现了芍药内酯 B 的新立体选择性合成，总产率为 11.5%。关键合成步骤基于区域选择性金属化以及区域和非对映选择性环氧化。