5-甲基-5-己烯-2-醇 | 50551-88-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 5-甲基-5-己烯-2-醇
• 英文名称: 5-methylhex-5-en-2-ol
• 英文别名: 5-methyl-5-hexen-2-ol；2-Methyl-hexen-(1)-ol-(5)
• CAS: 50551-88-7
• 化学式: C₇H₁₄O
• 分子量: 114.188
• InChiKey: RIEDLCPIEKXTTL-UHFFFAOYSA-N

物化性质

• 沸点：
  73-74 °C(Press: 26.5-28.5 Torr)
• 密度：
  0.834±0.06 g/cm3(Predicted)
• LogP：
  1.548 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2905290000

反应信息

• 作为反应物：
  描述：

  5-甲基-5-己烯-2-醇 在 吡啶 、 2-萘硫醇 作用下， 以 氘代苯 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.08h， 生成 2,2,5-Trimethyl-tetrahydro-furan
  参考文献：
  名称：

  Ring Closure Reactions of Substituted 4-Pentenyl-1-oxy Radicals. The Stereoselective Synthesis of Functionalized Disubstituted Tetrahydrofurans

  摘要：

  N-(Alkyloxy)pyridine-2( VT)-thiones 3 and benzenesulfenic acid O-esters 5 have been synthesized from substituted 4-pentenols 1 or the derived tosylates. Compounds 3 and 5 are efficient sources of free alkoxy radicals 6 which undergo synthetically useful fast ring closure reactions 6 --> 8 [k(exo) = (2 +/- 1) x 10(8) s(-1) to (6 +/- 2) x 10(9) s(-1) (T = 30 +/- 0.2 degrees C)]. Tetrahydrofurfuryl radicals 8 can be trapped with, e.g., hydrogen or chlorine atom donors to afford either trans- or cis-disubstituted tetrahydrofurans 10 or 12 depending on the substitution pattern of the 4-pentenyloxy radical. Substituted tetrahydropyrans 11 or 13 are formed in the minor 6-endo-trig cyclization. According to the data of competition kinetics, the observed stereoselectivities in free alkoxy radical cyclizations arise from steric interactions between the substituents in the transition state of the ring closure reactions. Alkyl substituents cause small differences in the measured relative rate constants of B-exo cyclizations which are reminiscent of the data obtained from the rearrangements of alkyl-substituted 5-hexenyl radicals. Likewise, a stereochemical model for oxygen radical cyclization is proposed where the pentenyloxy chain adopts a six-membered, chairlike transition state with the alkyl substituents preferentially situated in the pseudoequatorial positions leading to 2,5-trans-, 2,4-cis-, and 2,3-trans-substituted tetrahydrofurfuryl radicals 8 as the major intermediates.

  DOI：

  10.1021/jo00126a021
• 作为产物：
  描述：

  2,5-己二醇 在 吡啶 、 水 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 生成 5-甲基-5-己烯-2-醇
  参考文献：
  名称：

  VIII族金属催化剂在非共轭烯酮加氢中的化学选择性

  摘要：

  VIII族金属催化剂的化学选择性已在常温氢气压力下非共轭烯酮的氢化中得到检验。钴催化剂从三烷基化烯烃酮中得到高收率的不饱和醇。在铂金属催化剂中，锇在三烷基化烯烃酮的加氢反应中对羰基键的还原显示出最高的选择性。无论催化剂如何，单烷基化和二烷基化烯烃酮的氢化通常以烯烃官能团的优先饱和进行。4-亚甲基-和4-亚乙基环己酮的氢化伴随着在乙醇溶剂中在钌、铑和钯黑催化剂上形成二乙缩醛。在其他烯酮的氢化和其他催化剂上未检测到缩醛。此外，还研究了镍和钴催化剂对无环烯酮加氢的化学选择性。

  DOI：

  10.1246/bcsj.60.1721

文献信息

• Cooperative Mn(<scp>i</scp>)-complex catalyzed transfer hydrogenation of ketones and imines
  作者：Kasturi Ganguli、Sujan Shee、Dibyajyoti Panja、Sabuj Kundu

  DOI：10.1039/c8dt05001e

  日期：——

  complex presented higher reactivity in the transfer hydrogenation (TH) of ketones in 2-propanol. Experimentally, it was established that both the benzimidazole and amine N–H proton played a vital role in the enhancement of the catalytic activity. Utilizing this system a wide range of aldehydes and ketones were reduced efficiently. Notably, the TH of several imines, as well as chemoselective reduction of

  据报道，带有双功能配体的Mn（I）配合物的合成和反应性均包含胺N-H和苯并咪唑片段。在各种配体中，含Mn（I）的N -（（1 H-苯并咪唑-2-基）甲基）苯胺配体）配合物在2-丙醇中酮的转移加氢（TH）中表现出更高的反应性。实验确定，苯并咪唑和胺NH质子均在增强催化活性中起着至关重要的作用。使用该系统可以有效地减少各种醛类和酮类。值得注意的是，在该催化剂的存在下，实现了几种亚胺的TH以及不饱和酮的化学选择性还原。进行DFT计算以了解合理的反应机理，该机理揭示了转移氢化反应遵循协调的外球机理。
• 6,6′-Dihydroxy terpyridine: a proton-responsive bifunctional ligand and its application in catalytic transfer hydrogenation of ketones
  作者：Cameron M. Moore、Nathaniel K. Szymczak

  DOI：10.1039/c2cc36927c

  日期：——

  The ligand 6,6′-dihydroxy terpyridine (dhtp) is presented as a bifunctional ligand capable of directing proton transfer events with metal-coordinated substrates. Solid-state analysis of a Ru(II)-dhtp complex reveals directed hydrogen-bonding interactions of the hydroxyl groups of dhtp with a Ru-bound chloride ligand. The utility of dhtp was demonstrated by chemoselective transfer hydrogenation of ketones.

  配体6,6'-二羟基三吡啶（dhtp）被介绍为一种双功能配体，能够指导与金属配位底物间的质子传递事件。对Ru(II)-dhtp配合物的固态分析揭示了dhtp羟基与Ru结合的氯配体之间的定向氢键相互作用。通过酮的选择性转移氢化反应，展示了dhtp的实用性。
• 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。
• Compounds capable of activating cholinergic receptors
  申请人：——

  公开号：US20030125345A1

  公开（公告）日：2003-07-03

  The present invention generally relates to nicotinic compounds, in the form of aryl substituted olefinic compounds, as well as pro-drug, N-oxide, metabolite and pharmaceutically acceptable salt forms thereof. Methods of modulating neurotransmitter release via administration of the compounds, pro-drugs, N-oxides and/or pharmaceutically acceptable salts are also disclosed.

  本发明通常涉及烟碱化合物，以芳基取代的烯烃化合物形式存在，以及它们的前药、N-氧化物、代谢物和药用可接受盐形式。还公开了通过给予这些化合物、前药、N-氧化物和/或药用可接受盐来调节神经递质释放的方法。
• 5-(Methylthio)tetrazoles as versatile synthons in the stereoselective synthesis of polycyclic pyrazolines via photoinduced intramolecular nitrile imine–alkene 1,3-dipolar cycloaddition
  作者：Daniel Pla、Derek S. Tan、David Y. Gin

  DOI：10.1039/c4sc00107a

  日期：——

  A key thioether substituent in readily accessible 2-alkyl-5-(methylthio)tetrazoles enables facile photoinduced denitrogenation and intramolecular nitrile imine 1,3-dipolar cycloaddition to afford a wide range of polycyclic pyrazoline products with excellent diastereoselectivity. The methylthio group red-shifts the UV absorbance of the tetrazole, obviating the requirement in all previous substrate systems

  易于获得的 2-烷基-5-（甲硫基）四唑中的一个关键硫醚取代基能够轻松进行光诱导脱氮和分子内腈亚胺 1,3-偶极环加成反应，从而提供多种具有优异非对映选择性的多环吡唑啉产物。甲硫基使四唑的紫外吸光度发生红移，避免了之前所有底物系统对至少一个芳基取代基的要求，并且随后可以转化为各种其他官能团。该合成平台已应用于生物碱天然产物(±)-newbouldine和withasomnine的简明全合成。

表征谱图