3-甲基-2-己醇 | 2313-65-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-甲基-2-己醇
• 中文别名: 3-甲基己烷-2-醇
• 英文名称: threo-3-Methyl-2-hexanol
• 英文别名: 3-Methyl-2-hexanol；3-methylhexan-2-ol
• CAS: 2313-65-7
• 化学式: C₇H₁₆O
• mdl: MFCD00021889
• 分子量: 116.203
• InChiKey: IRLSKJITMWPWNY-UHFFFAOYSA-N

物化性质

• 熔点：
  -30.45°C (estimate)
• 沸点：
  151.5°C
• 密度：
  0.8220
• LogP：
  2.055 (est)
• 保留指数：
  906;909;914.3

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2905199090

反应信息

• 作为反应物：
  描述：

  3-甲基-2-己醇 在 sodium dichromate 、 硫酸 作用下， 以 乙醚 为溶剂， 生成 3-甲基-2-己酮
  参考文献：
  名称：

  Charge-Reversal mass spectra of enolate ions of some open-chain and cyclic ketones for structure identification

  摘要：

  AbstractThe charge‐reversal (CR) mass spectra of the enolate ions of heptanal and ten isomeric heptanones, of cyclohexanone, of cycloheptanone, of isomeric methylcyclohexanones, of isomeric ethylcyclohexanones and of the iso meric monoterpene ketones camphor, fenchone, pulegone and thujone were obtained by deprotonation using OH− under chemical ionization conditions followed by collision of the [M − H] − ions with helium in the second field‐free region of a VG ZAB 2F mass spectrometer. The CR mass spectra were evaluated by similarity index (SI) values. Characteristic of the CR mass spectra of the open‐chain enolates are fragment ions formed by α‐cleavage. However, the CR mass spectra are dominated by peaks of small hydrocarbon ions, particularly in the case of cyclic and bicyclic enolates. The CR mass spectra of enolates of linear heptanones differing in the position of the carbonyl group can be easily correlated with the structure of the parent ketone. The CR mass spectra of enolates of isomeric heptan‐2‐ones differing only in the degree of branching of the alkyl group are similar, but can be distinguished by the SI values. The CR mass spectra of the enolates of the isomeric cyclic and bicyclic ketones studied are more or less identical and cannot be used for structural assignment.

  DOI：

  10.1002/oms.1210250903
• 作为产物：
  描述：

  3-甲基己-3-烯-2-醇 在 乙醚 、 氢气 、 铂 作用下， 生成 3-甲基-2-己醇
  参考文献：
  名称：

  Bjelouss, Chemische Berichte, 1912, vol. 45, p. 627

  摘要：

  DOI：

文献信息

• Oxidations catalyzed by osmium compounds. Part 1: Efficient alkane oxidation with peroxides catalyzed by an olefin carbonyl osmium(0) complex
  作者：Georgiy B. Shul’pin、Aleksandr R. Kudinov、Lidia S. Shul’pina、Elena A. Petrovskaya

  DOI：10.1016/j.jorganchem.2005.10.028

  日期：2006.2

  4-diphenylbut-2-en-1,4-dione)undecacarbonyl triangulotriosmium (1), efficiently catalyzes oxygenation of alkanes (cyclohexane, cyclooctane, n-heptane, isooctane, etc.) with hydrogen peroxide, as well as with tert-butyl hydroperoxide and meta-chloroperoxybenzoic acid in acetonitrile solution. Alkanes are oxidized to corresponding alcohols, ketones (aldehydes) and alkyl hydroperoxides. Thus, heating cyclooctane with the

  与π配位烯烃（2,3-η-1,4-diphenylbut-2-en-1,4-dione）十一碳羰基三氟ang（1）形成的羰基os（0）有效催化链烷烃（环己烷，环辛烷，正庚烷，异辛烷等），过氧化氢以及叔丁基氢过氧化物和间氯过氧苯甲酸的乙腈溶液。烷烃被氧化为相应的醇，酮（醛）和烷基氢过氧化物。因此，用1 –H 2 O 2加热环辛烷在70°C下混合后，经过6小时后，产品的营业额高达2400。以环己烷计，所有产物的最大产率均等于20％，以H 2 O 2计，则为30％。直链和支链烷烃的氧化表现出非常低的区域选择性和键选择性参数，这证明该反应是通过羟基自由基攻击烷烃的CH键进行的。当在氩气氛下进行反应时，没有形成氧合产物，因此可以得出结论，氧合是通过烷基与大气氧之间的反应而发生的。总而言之，Os（0）络合物比任何可溶的铁衍生物（在周期系统中是analogue的类似物）都更强大地产生羟基自由基。
• Aliphatic Radical Relay Heck Reaction at Unactivated C(sp ³ )−H Sites of Alcohols
  作者：Padon Chuentragool、Dongari Yadagiri、Taiki Morita、Sumon Sarkar、Marvin Parasram、Yang Wang、Vladimir Gevorgyan

  DOI：10.1002/anie.201812398

  日期：2019.2.4

  aliphatic alcohols at unactivated β-, γ-, and δ-C(sp3 )-H sites. The use of an easily installed/removed Si-based auxiliary enables selective I-atom/radical translocation events at remote C-H sites followed by the Heck reaction. Notably, the reaction proceeds smoothly under mild visible-light-mediated conditions at room temperature, producing highly modifiable and valuable alkenol products from readily available

  Mizoroki-Heck反应是使芳基，乙烯基和烷基卤化物进行烯基化的最有效方法之一。鉴于其固有的性质，该方案要求使用在官能化位点具有卤素原子的化合物。但是，在脂族体系中特定位置具有卤原子的有机分子的可及性受到极大限制。因此，期望允许Heck反应在特定的未官能化的C（sp3）-H位点发生的方案。此处报道的是一种自由基中继Heck反应，该反应允许脂族醇在未活化的β-，γ-和δ-C（sp3）-H位点进行选择性的远程烯基化。使用易于安装/拆卸的硅基助剂可以在遥远的CH位点进行选择性的I原子/自由基易位事件，然后发生Heck反应。尤其，
• Alkane oxygenation catalysed by gold complexes
  作者：Georgiy B. Shul'pin、Alexander E. Shilov、Georg Süss-Fink

  DOI：10.1016/s0040-4039(01)01517-9

  日期：2001.10

  involve the participation of free hydroxyl radicals. Possibly, the oxidation begins from the alkane hydrogen atom abstraction by a gold oxo species. The oxidation of cyclooctane by air at room temperature catalysed by NaAuCl4 in the presence of Zn/CH3COOH as a reducing agent and methylviologen as an electron-transfer agent gave cyclooctanol (TON=10).

  金（III）和金（I）配合物NaAuCl 4和ClAuPPh 3可以有效地催化H 2 O 2在乙腈溶液中于75°C氧化烷烃。144小时后，营业额（TON）达到520。烷基氢过氧化物是主要产物，而酮（醛）和醇的浓度较低。根据键的选择性研究建议，Au催化的烷烃加氢过氧化反应的至少一种途径不涉及游离羟基的参与。氧化可能是由含金氧种从烷烃氢原子的提取开始的。在Zn / CH存在下NaAuCl 4催化的室温空气中环辛烷的氧化用3COOH作为还原剂和甲基紫罗兰作为电子转移剂，得到环辛醇（TON ＝ 10）。
• Alkane oxygenation with H2O2 catalysed by FeCl3 and 2,2′-bipyridine
  作者：Georgiy B. Shul’pin、Camilla C. Golfeto、Georg Süss-Fink、Lidia S. Shul’pina、Dalmo Mandelli

  DOI：10.1016/j.tetlet.2005.05.007

  日期：2005.7

  acetonitrile efficiently oxidises alkanes predominantly to alkyl hydroperoxides. Turnover numbers attain 400 after 1 h at 60 °C. It has been assumed that bipy facilitates proton abstraction from a H2O2 molecule coordinated to the iron ion (these reactions are stages in the catalytic cycle generating hydroxyl radicals from the hydrogen peroxide). Hydroxyl radicals then attack alkane molecules finally yielding

  乙腈中的H 2 O 2 -FeCl 3-联吡啶系统可有效地将烷烃氧化为烷基氢过氧化物。在60°C下放置1 h后，周转次数达到400。假定联吡啶有助于从与铁离子配位的H 2 O 2分子中提取质子（这些反应是催化循环中由过氧化氢产生羟基自由基的阶段）。然后，羟基自由基攻击烷烃分子，最终产生烷基氢过氧化物。
• Revision of species of the “<i>Oligia</i>” <i>semicana</i> group (Lepidoptera: Noctuidae) with descriptions of a new genus and 12 new species
  作者：James T. Troubridge、J. Donald Lafontaine

  DOI：10.4039/ent134157-2

  日期：2002.4

  The name Neoligiagen.nov. is proposed for the “Oligia” semicana (Walker) species group in North America and 12 species, N. rubirena sp.nov., N. pagosa sp.nov., N. hardwicki sp.nov., N. inermis sp.nov., N. invenusta sp.nov., N. albirena sp.nov., N. lancea sp.nov., N. elephas sp.nov., N. lillooet sp.nov., N. surdirena sp.nov., N. canadensis sp.nov., and N. atlantica sp.nov. are described. Hadenella laevigata Smith is synonymized (synonymy restored) under Hadena tonsa Grote and Hadena hausta Grote is synonymized (synonymy restored) under Miana semicana Walker. Adults of all species are illustrated as well as male and female genitalia, where known.

  AbstractThe name Neoligiagen.nov. is proposed for the "Oligia" semicana (Walker) species group in North America and 12 species, N. rubirena sp.nov., N. pagosa sp.nov., N. hardwicki sp.nov、N. inermis sp.nov.、N. invenusta sp.nov.、N. albirena sp.nov.、N. lancea sp.nov.、N. elephas sp.nov.、N. lillooet sp.nov.、N. surdirena sp.nov.、N. canadensis sp.nov.和 N. atlantica sp.nov.等 12 个种。Hadenella laevigata Smith 与 Hadena tonsa Grote 同源（同义恢复），Hadena hausta Grote 与 Miana semicana Walker 同源（同义恢复）。所有物种的成体以及已知的雄性和雌性生殖器均附有插图。

表征谱图