(E)-4-Methyl-6-(2',6',6'-trimethyl-1'-cyclohexenyl)hex-3-en-1-ol | 110202-07-8

• 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: (E)-4-Methyl-6-(2',6',6'-trimethyl-1'-cyclohexenyl)hex-3-en-1-ol
• 英文别名: (E)-4-methyl-6-(2',6',6'-trimethylcyclohex-1'-enyl)-3-hexen-1-ol；(E)-4-methyl-6-(2,6,6-trimethylcyclohex-1-enyl)-hex-3-en-1-ol；4-methyl-6-(2,6,6-trimethyl-1-cyclohexenyl)-hex-3-en-1-ol；3-Hexen-1-ol, 6-(2,6,6-trimethyl-1-cyclohexenyl)-4-methyl-, (E)-；(E)-4-methyl-6-(2,6,6-trimethylcyclohexen-1-yl)hex-3-en-1-ol
• CAS: 110202-07-8
• 化学式: C₁₆H₂₈O
• 分子量: 236.398
• InChiKey: KPAPKRAHTYQTRQ-NTUHNPAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  (E)-4-Methyl-6-(2',6',6'-trimethyl-1'-cyclohexenyl)hex-3-en-1-ol 在 N,N-二甲基丙烯基脲 、 三氟化硼乙醚 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 生成 5-Hydroxy-4-{6-hydroxy-5-[(E)-4-methyl-6-(2,6,6-trimethyl-cyclohex-1-enyl)-hex-3-enyl]-3,6-dihydro-2H-pyran-2-yl}-5H-furan-2-one
  参考文献：
  名称：

  Total synthesis of manoalide

  摘要：

  DOI：

  10.1016/s0040-4039(00)84996-5
• 作为产物：
  描述：

  Diethyl 4-(2,6,6-trimethylcyclohexen-1-yl)but-1-en-2-yl phosphate 在 正丁基锂 、 zirconocene dichloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 24.0h， 生成 (E)-4-Methyl-6-(2',6',6'-trimethyl-1'-cyclohexenyl)hex-3-en-1-ol
  参考文献：
  名称：

  Two syntheses of manoalide via heteroatom-assisted alkyne carbometallation

  摘要：

  Two approaches to the sesterterpenoid phospholipase A(2) inhibitors seco-manoalide (3) and manoalide (1) are described based on carbometallation of propargylic alcohols to generate the functionalised C6-C7 trisubstituted alkene. Both syntheses also deploy the photooxidation of a furan in order to generate a 4-substituted-5-hydroxy-2(5H)-furanone moiety.

  DOI：

  10.1016/s0040-4020(01)85353-9

文献信息

• Synthesis of (+)-Manoalide via a Copper(I)-Mediated 1,2-Metalate Rearrangement
  作者：Agnès Pommier、Viatcheslav Stepanenko、Krzysztof Jarowicki、Philip J. Kocienski

  DOI：10.1021/jo0268097

  日期：2003.5.1

  (+)-(4R)-manoalide is reported in which all 25 carbons of the sesterterpenoid skeleton are constructed from 3-furaldehyde, trimethylalane, oxirane, CO, beta-ionone, and propargyl bromide. The overall yield for the longest linear sequence (12 steps) is 12%. Key steps include (a) a zirconium-catalyzed carboalumination reaction to construct the C10-C11 trisubstituted alkene, (b) a Cu(I)-mediated 1,2-metalate rearrangement

  对映体合成的磷脂酶A（2）抑制剂（+）-（4R）-马来酰内酯，其中酯类萜骨架的所有25个碳原子均由3-呋喃醛，三甲基铝烷，环氧乙烷，CO，β-紫罗兰酮和炔丙基构成溴化物。最长的线性序列（12个步骤）的总产率为12％。关键步骤包括（a）锆催化的碳铝化反应以构建C10-C11三取代的烯烃，（b）Cu（I）介导的1,2-金属盐重排以构建C6-C7三取代的烯烃，（c）a锐利的动力学拆分，可确保（4R）-立体化学，（d）通过Mo催化的高炔丙醇的环异构化反应生成5-stannyl-2,3-dihydrofuran，以及（e）通过光氧化α-羟基呋喃酮环来构建羟基呋喃酮环甲硅烷基呋喃。
• [EN] HYDROGENATION OF CARBONYLS WITH TETRADENTATE PNNP LIGAND RUTHENIUM COMPLEXES<br/>[FR] HYDROGÉNATION DE CARBONYLES AVEC DES COMPLEXES DE RUTHÉNIUM - LIGAND TÉTRADENTATE PNNP
  申请人：FIRMENICH & CIE

  公开号：WO2019175158A1

  公开（公告）日：2019-09-19

  The present invention relates to catalytic hydrogenation processes, using Ru complexes with tetradentate ligands of formula L in hydrogenation processes for the reduction of ketone, aldehyde, ester or lactone into the corresponding alcohol or diol respectively. The described processes use a ruthenium complex of the formula (1) as defined below, and where the ligand (L) is defined by the Markush formula shown above.

  本发明涉及催化加氢过程，使用具有四齿配体L的Ru配合物在加氢过程中将酮、醛、酯或内酯还原为相应的醇或二醇。所述过程使用下文所定义的化学式（1）的钌配合物，并且配体（L）由上述Markush式定义。
• Simple metal salts supported on montmorillonite as recyclable catalysts for intramolecular hydroalkoxylation of double bonds in conventional and VOC-exempt solvents
  作者：Irene Notar Francesco、Bastien Cacciuttolo、Mathieu Pucheault、Sylvain Antoniotti

  DOI：10.1039/c4gc01990c

  日期：——

  hydroalkoxylation of double bonds. A heterogeneous catalyst based on the impregnation of benign metals such as iron and bismuth on montmorillonite was used for a highly atom-economic transformation in DMC, a non-VOC solvent. The transformation allowed the formation of a large range of cyclic ethers from the corresponding unsaturated alcohols and the catalyst could be recycled several times.

  我们在本文中描述了用于双键的分子内氢烷氧基化的有效且特别可持续的催化体系。基于在蒙脱石上浸渍铁和铋等良性金属的非均相催化剂用于非VOC溶剂DMC中的高度原子经济转化。该转化允许由相应的不饱和醇形成大范围的环醚，并且催化剂可以循环几次。
• Synthesis of (S)-manoalide diol and the absolute configuration of natural manoalide
  作者：Victor Ekow Amoo、Silvano De Bernardo、Manfred Weigele

  DOI：10.1016/s0040-4039(00)87892-2

  日期：1988.1

  A synthesis of (S)-manoalide diol (2a) has been achieved using 2-deoxy-D-ribose as starting material to unequivocally supply the stereochemistry. Reduction of natural manoalide afforded enantiomeric manoalide diol 2b. Thus, the absolute configuration of manoalide is R (as depicted in 1).

  使用2-脱氧-D-核糖作为起始材料明确地提供立体化学，已经实现了（S）-甘露糖醇二醇（2a）的合成。还原天然的山梨糖醇得到对映体的山梨糖醇二醇2b。因此，山梨醇内酯的绝对构型为R（如1所示）。
• METHOD FOR SYNTHESISING AMBROXIDE FROM AGERATINA JOCOTEPECANA
  申请人：UNIVERSIDAD MICHOACANA DE SAN NICOLÁS DE HIDALGOú

  公开号：US20190023679A1

  公开（公告）日：2019-01-24

  The present invention is related to a process for obtaining the (−)-13,14,15,16-tetranor-8a,12-labdanediol compound from the Ageratina jocotepecana plant, the process comprises the steps of a) obtaining an organic concentrated extract from the Ageratina jocotepecana shoot system; b) subjecting the organic concentrated extract to column chromatography in order to elute a fraction with the (−)-13,14,15,16-tetranor-8a,12-labdanediol compound; c) separating the eluted fractions comprising the (−)-13,14,15,16-tetranor-8a,12-labdanediol compound; and d) evaporating the organic solvent to yield the (−)-13,14,15,16-tetranor-8a,12-labdanediol compound in a solid form.

  本发明涉及一种从Ageratina jocotepecana植物中获取(−)-13,14,15,16-四去甲基-8a,12-拉丹二醇化合物的方法，包括以下步骤：a)从Ageratina jocotepecana茎系统中提取有机浓缩物；b)将有机浓缩物经过柱层析以洗脱出含有(−)-13,14,15,16-四去甲基-8a,12-拉丹二醇化合物的分离物；c)分离含有(−)-13,14,15,16-四去甲基-8a,12-拉丹二醇化合物的洗脱分离物；d)蒸发有机溶剂以得到以固体形式存在的(−)-13,14,15,16-四去甲基-8a,12-拉丹二醇化合物。