(E)-3-methyl-3-penten-1-ol | 1594-24-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-3-methyl-3-penten-1-ol
• 英文别名: (E)-3-methylpent-3-en-1-ol；(E)-4-methyl-isoprenol；trans-3-Methyl-pent-3-en-1-ol；3-Methyl-3-penten-1-ol
• CAS: 1594-24-7
• 化学式: C₆H₁₂O
• 分子量: 100.161
• InChiKey: SZPKMIRLEAFMBV-ZZXKWVIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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)-3-methyl-3-penten-1-ol 在 吡啶 、 对甲苯磺酰氯 作用下， 生成 5-iodo-3-methyl-pent-2t-ene
  参考文献：
  名称：

  685.还原的环状化合物。第五部分。5：6-二氢-3-甲基-4 H-吡喃的制备及其转化为4-甲基-己基-反式-4-烯-1-醇

  摘要：

  DOI：

  10.1039/jr9580003388
• 作为产物：
  描述：

  dimethylisopropoxy((E)-3-methyl-3-butenyl)silane 在 双氧水 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以34%的产率得到(E)-3-methyl-3-penten-1-ol
  参考文献：
  名称：

  Chemistry of dioxenium cations. Synthetic and mechanistic studies on the stereocontrolled formation of tetrahydropyrans from homoallylic alcohols and ortho esters

  摘要：

  Despite their long history, dioxenium cations are underutilized reactive synthetic intermediates. It was found that ortho esters and homoallylic alcohols in the presence of Lewis acids provide 4-heterosubstituted pyranosides in a stereoselective manner. The mechanistic course of events was supported by control experiments and synthesis of a putative mixed ortho ester intermediate which exhibited identical reactivity. A transition state for termination of the dioxenium cation-olefin cyclization is proposed, involving intramolecular delivery of chloride by a coordinated tin species. Structure-reactivity relationships indicate that a cation-stabilizing substituent (alkyl or alkoxy) at the internal position of the olefin is required for cyclization. A variety of 3-alkyl-substituted homoallylic alcohols cyclize cleanly to substituted 2-alkoxytetrahydropyrans in good yield. beta-silyloxy silyl enol ethers were found to smoothly provide 4-oxotetrahydropyranosides when subjected to the same reaction conditions. For these substrates, the course of the cyclization proceeds in a different manner involving a rapid intermolecular Mukaiyama aldol condensation followed by transacetalization.

  DOI：

  10.1021/jo00021a043

文献信息

• METHOD FOR PRODUCING OLEFINICALLY UNSATURATED CARBONYL COMPOUNDS BY OXIDATIVE DEHYDROGENATION OF ALCOHOLS
  申请人：Limbach Michael

  公开号：US20110004025A1

  公开（公告）日：2011-01-06

  A process for preparing olefinically unsaturated carbonyl compounds by oxidative dehydrogenation in an oxygenous atmosphere over a supported catalyst which comprises gold and optionally further noble metals at temperatures in the range from 50 to 240° C.

  在氧气气氛中，通过在温度范围为50到240°C之间使用含金和可选的其他贵金属的支持催化剂进行氧化脱氢，制备烯烃不饱和羰基化合物的方法。
• [DE] VERFAHREN ZUR HERSTELLUNG VON 3-PHENYL(THIO)URACILEN UND - DITHIOURACILEN<br/>[EN] METHOD FOR THE PRODUCTION OF 3-PHENYL(THIO)URACILS AND DITHIOURACILS<br/>[FR] PROCEDE DE PRODUCTION DE 3-PHENYL(THIO)URACILES ET DE 3-PHENYL-DITHIO-URACILES
  申请人：BASF AG

  公开号：WO2006010474A1

  公开（公告）日：2006-02-02

  Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung von 3-Phenyl(thio)uracilen und -dithiouracilen der Formel I, worin die Variablen die in der Beschreibung genannten Bedeutungen haben, dadurch gekennzeichnet, dass Carbamate der Formel II, wobei die Variablen X1, X3, Ar und A die zuvor genannten Bedeutungen haben und L1für eine nucleophil verdrängbare Abgangsgruppe steht, mit Enaminen der Formel III, wobei die Variablen X2, R1, R2 und R3 die zuvor genannten Bedeutungen haben und L2 für eine nucleophil verdrängbare Abgangsgruppe steht, umgesetzt werden, sowie Zwischenprodukte zu ihrer Herstellung.

  这项发明涉及一种制备式I的3-苯基(硫)尿嘧啶和-二硫尿嘧啶的方法，其中变量具有描述中提到的含义，其特征在于，将式II的氨基甲酸酯与式III的烯胺反应，其中变量X1、X3、Ar和A具有前述含义，L1代表一个亲核可替代的离去基团，X2、R1、R2和R3具有前述含义，L2代表一个亲核可替代的离去基团，以及用于制备它们的中间体。
• Method for producing anellated tetrahydro-{1h}-triazoles
  申请人：——

  公开号：US20040097728A1

  公开（公告）日：2004-05-20

  The present invention relates to a process for preparing fused tetrahydro-[ 1 H]-triazoles of the formula I 1 where the variables R a , Z, Z 1 , X, W, n and Q are as defined in claim 1, by cyclization of compounds of the formula II 2 where R is C(X)OR 2 or C(X)SR 2 , where X is oxygen or sulfur, and R 2 is as defined in claim 1, in the presence of a base. The invention also relates to compounds of the formula I where W is sulfur if Z is a methylene group optionally substituted by R a , and furthermore to compounds of the formula I where Q is a benzoxazole or benzothiazole radical, and to the use of these compounds as herbicides.

  本发明涉及一种制备公式I的熔融四氢咪唑的方法，其中变量Ra、Z、Z1、X、W、n和Q如权利要求1中定义，通过在碱存在下，将公式II的化合物环化得到，其中R为C(X)OR2或C(X)SR2，其中X为氧或硫，R2如权利要求1中定义。该发明还涉及公式I的化合物，其中如果Z是可选地由Ra取代的亚甲基基团，则W为硫，此外还涉及公式I的化合物，其中Q为苯并噁唑或苯并噻唑基团，并将这些化合物用作除草剂。
• Enzymatic Synthesis of Methylated Terpene Analogues Using the Plasticity of Bacterial Terpene Synthases
  作者：Anwei Hou、Lukas Lauterbach、Jeroen S. Dickschat

  DOI：10.1002/chem.201905827

  日期：2020.2.17

  Methylated analogues of isopentenyl diphosphate were synthesised and enzymatically incorporated into methylated terpenes. A detailed stereochemical analysis of the obtained products is presented. The methylated terpene precursors were also used in conjunction with various isotopic labellings to gain insights into the mechanisms of their enzymatic formation.

  合成了异戊烯基二磷酸的甲基化类似物，并通过酶法将其掺入甲基化萜烯中。给出了所得产物的详细立体化学分析。甲基化萜烯前体还与各种同位素标记结合使用，以深入了解其酶促形成的机制。
• Solvent-controlled additions of organotitanium reagents to olefinic double bonds
  作者：Etienne Moret、Manfred Schlosser

  DOI：10.1016/s0040-4039(00)88920-0

  日期：1985.1

  Under carefully chosen working conditions (solvent, temperature), methyltitanium reagents smoothly convert homoallyl alcohols having a terminal double-bond into (E)-3-penten-l-ols whereas non-terminal 3-alken-l-ols afford 4-methyl-branched derivatives with configurational inversion of the chain (Z → E; E → Z), stereoselectivities being better than 99%.

  在精心选择的工作条件（溶剂，温度）下，甲基钛试剂可将具有末端双键的均烯丙基醇平稳地转化为（E）-3-戊烯-1-醇，而非末端的3-烯丙基-1-醇可提供4-甲基-链支链的衍生物，具有链的构型反转（Z→E； E→Z），立体选择性优于99％。