2,2,6-三甲基-6-乙烯基四氢-2H-呋喃-3-醇 | 14049-11-7

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 中文名称: 2,2,6-三甲基-6-乙烯基四氢-2H-呋喃-3-醇
• 中文别名: 2,2,6-三甲基-6-乙烯基四氢吡喃-3-醇；2,2,6-三甲基-6-乙烯基四氢-2H-吡喃-3-醇；2,2,6-三甲基-6-乙烯基四氢吡喃-3-醇(异构体的混和物)；3-羟基-2,2,6-三甲基-6-乙烯基四氢吡喃
• 英文名称: 3-hydroxy-2,2,6-trimethyl-6-vinyltetrahydropyran
• 英文别名: 2,2,6-trimethyl-6-vinyltetrahydropyran-3-ol；6-ethenyltetrahydro-2,2,6-trimethyl-2H-pyran-3-ol；2,2,6-trimethyl-6-vinyltetrahydro-2H-pyran-3-ol；pyranoid；Pyranoid-linalool oxide；2H-Pyran-3-ol, 6-ethenyltetrahydro-2,2,6-trimethyl-；6-ethenyl-2,2,6-trimethyloxan-3-ol
• CAS: 14049-11-7
• 化学式: C₁₀H₁₈O₂
• mdl: MFCD06200770
• 分子量: 170.252
• InChiKey: BCTBAGTXFYWYMW-UHFFFAOYSA-N

物化性质

• 沸点：
  98°C/10mmHg(lit.)
• 密度：
  0.988±0.06 g/cm3(Predicted)
• 闪点：
  100°C(lit.)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）
• LogP：
  1.87
• 物理描述：
  Colourless to pale yellow liquid; floral aroma
• 折光率：
  1.472-1.482
• 保留指数：
  1131;1136;1198;1176;1168;1149;1164;1164;1168;1147;1160;1169;1165;1150;1174;1145

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xn
• 危险类别码：
  R22
• 海关编码：
  2932999099
• 储存条件：
  室温

SDS

---

Section I.Chemical Product and Company Identification
Chemical Name 2,2,6-Trimethyl-6-vinyltetrahydropyran-3-ol
(mixture of isomers)
Portland OR
2H-Pyran-3-ol, 6-ethenyltetrahydro-2,2,6-trimethyl-
Synonym
(CA INDEX NAME); Linalool Oxide Pyranoid;
3-Hydroxy-2,2,6-trimethyl-6-vinyltetrahydropyran
Chemical Formula C10H18O2
CAS Number 14049-11-7

---

Section II. Composition and Information on Ingredients
CAS Number Percent (%) TLV/PEL Toxicology Data
Chemical Name
2,2,6-Trimethyl-6-vinyltetrahydropyran-3-ol 14049-11-7 Min. 98.0 (GC) Not available. Not available.
(mixture of isomers)

---

Section III. Hazards Identification
Acute Health Effects Irritating to eyes and skin on contact. Inhalation causes irritation of the lungs and respiratory system. Inflammation of the
eye is characterized by redness, watering, and itching. Skin inflammation is characterized by itching, scaling, reddening, or,
occasionally, blistering.
Follow safe industrial hygiene practices and always wear proper protective equipment when handling this compound.
Chronic Health Effects CARCINOGENIC EFFECTS : Not available.
MUTAGENIC EFFECTS : Not available.
TERATOGENIC EFFECTS : Not available.
DEVELOPMENTAL TOXICITY: Not available.
Repeated or prolonged exposure to this compound is not known to aggravate existing medical conditions.

---

Section IV. First Aid Measures
Eye Contact Check for and remove any contact lenses. In case of contact, immediately flush eyes with plenty of water for at least 15
minutes. Get medical attention.
Skin Contact In case of contact, immediately flush skin with plenty of water. Remove contaminated clothing and shoes. Wash clothing
before reuse. Thoroughly clean shoes before reuse. Get medical attention.
If the victim is not breathing, perform mouth-to-mouth resuscitation. Loosen tight clothing such as a collar, tie, belt or
Inhalation
waistband. If breathing is difficult, oxygen can be administered. Seek medical attention if respiration problems do not
improve.
INDUCE VOMITING by sticking finger in throat. Lower the head so that the vomit will not reenter the mouth and throat.
Ingestion
Loosen tight clothing such as a collar, tie, belt or waistband. If the victim is not breathing, perform mouth-to-mouth
resuscitation. Examine the lips and mouth to ascertain whether the tissues are damaged, a possible indication that the toxic
material was ingested; the absence of such signs, however, is not conclusive.

---

Section V. Fire and Explosion Data
Not available.
May be combustible at high temperature. Auto-Ignition
Flammability
Flash Points Flammable Limits Not available.
Not available.
Combustion Products These products are toxic carbon oxides (CO, CO2).
Fire Hazards
Not available.
Risks of explosion of the product in presence of mechanical impact: Not available.
Explosion Hazards
Risks of explosion of the product in presence of static discharge: Not available.
Fire Fighting Media SMALL FIRE: Use DRY chemical powder.
and Instructions LARGE FIRE: Use water spray, fog or foam. DO NOT use water jet.
Consult with local fire authorities before attempting large scale fire-fighting operations.
Continued on Next Page
2,2,6-Trimethyl-6-vinyltetrahydropyran-3-ol
(mixture of isomers)

---

Section VI. Accidental Release Measures
Spill Cleanup Irritating material.
Absorb with an inert material and put the spilled material in an appropriate waste disposal. Finish cleaning the spill by rinsing
Instructions
any contaminated surfaces with copious amounts of water. Consult federal, state, and/or local authorities for assistance on
disposal.

---

Section VII. Handling and Storage
Handling and Storage IRRITANT. Keep away from heat. Mechanical exhaust required. When not in use, tightly seal the container and store in a
dry, cool place. Avoid excessive heat and light. Do not breathe gas/fumes/ vapor/spray.
Information
Always store away from incompatible compounds such as oxidizing agents.

---

Section VIII. Exposure Controls/Personal Protection
Provide exhaust ventilation or other engineering controls to keep the airborne concentrations of vapors below their respective
Engineering Controls
threshold limit value. Ensure that eyewash station and safety shower is proximal to the work-station location.
Splash goggles. Lab coat. Vapor respirator. Boots. Gloves. Suggested protective clothing might not be sufficient; consult a
Personal Protection
specialist BEFORE handling this product. Be sure to use a MSHA/NIOSH approved respirator or equivalent.
Exposure Limits Not available.

---

Section IX. Physical and Chemical Properties
Liquid. (Clear, colorless ~ light yellow.) Solubility
Physical state @ 20°C Not available.
Not available.
Specific Gravity
170.25
Molecular Weight Partition Coefficient Not available.
Boiling Point 98°C (208.4°F) @ 10 mmHg Vapor Pressure Not available.
Not available. Not available.
Melting Point Vapor Density
Not available. Volatility Not available.
Refractive Index
Not available.
Critical Temperature Not available. Odor
Viscosity Not available. Taste Not available.

---

Section X. Stability and Reactivity Data
Stability

---

This material is stable if stored under proper conditions. (See Section VII for instructions)
Conditions of Instability Avoid excessive heat and light.
Incompatibilities
Reactive with oxidizing agents.

---

Section XI. Toxicological Information
Not available.
RTECS Number
Routes of Exposure Eye Contact. Ingestion. Inhalation.
Not available.
Toxicity Data
Chronic Toxic Effects CARCINOGENIC EFFECTS : Not available.
MUTAGENIC EFFECTS : Not available.
TERATOGENIC EFFECTS : Not available.
DEVELOPMENTAL TOXICITY: Not available.
Repeated or prolonged exposure to this compound is not known to aggravate existing medical conditions.
Acute Toxic Effects Irritating to eyes and skin on contact. Inhalation causes irritation of the lungs and respiratory system. Inflammation of the eye
is characterized by redness, watering, and itching. Skin inflammation is characterized by itching, scaling, reddening, or,
occasionally, blistering.
Follow safe industrial hygiene practices and always wear proper protective equipment when handling this compound.

---

Section XII. Ecological Information
Not available.
Ecotoxicity
Environmental Fate Not available.
Continued on Next Page
2,2,6-Trimethyl-6-vinyltetrahydropyran-3-ol
(mixture of isomers)

---

Section XIII. Disposal Considerations
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material with a
Waste Disposal
combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system. Observe all
federal, state and local regulations when disposing of the substance.

---

Section XIV. Transport Information
DOT Classification Not a DOT controlled material (United States).
PIN Number Not applicable.
Proper Shipping Name Not applicable.
Packing Group (PG) Not applicable.
DOT Pictograms

---

Section XV. Other Regulatory Information and Pictograms
TSCA Chemical Inventory This compound is ON the EPA Toxic Substances Control Act (TSCA) inventory list.
(EPA)
WHMIS Classification On DSL.
(Canada)
EINECS Number (EEC) 237-889-1
EEC Risk Statements R36/37/38- Irritating to eyes, respiratory system and skin.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2,2,6-三甲基-6-乙烯基四氢-2H-呋喃-3-醇 在 C₄₄H₆₆O₈P₄Pd₂ 、 丁烯酮 作用下， 以 水 、 甲苯 为溶剂， 反应 16.0h， 以83%的产率得到6-ethenyl-5,6-dihydro-2,2,6-trimethyl-2H-pyran-3(4H)-one
  参考文献：
  名称：

  次膦氧化物作为多配位的配体在醇的化学选择性钯催化氧化中进行。

  摘要：

  通过吸氢方法，仲膦氧化物O = PHR 2（SPOs）被鉴定为化学选择的Pd催化醇氧化的多态预配体。发现SPO通过产生推定的活性H-Pd物种来促进氢的吸收步骤以及氢向迈克尔受体的转移。该催化体系在中性条件下运行，并被证明与底物中的各种亲电子和亲核官能团以及对水和空气敏感的官能团兼容。

  DOI：

  10.1002/cctc.201601261
• 作为产物：
  描述：

  在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以100%的产率得到2,2,6-三甲基-6-乙烯基四氢-2H-呋喃-3-醇
  参考文献：
  名称：

  Divergent Total Syntheses of Yaequinolone-Related Natural Products by Late-Stage C–H Olefination

  摘要：

  DOI：

  10.1021/acs.joc.1c00042

文献信息

• Selective epoxidation of monoterpenes with methyltrioxorhenium and H2O2
  作者：Aída L.P. de Villa、Dirk E. De Vos、Consuelo C. de Montes、Pierre A. Jacobs

  DOI：10.1016/s0040-4039(98)01853-x

  日期：1998.11

  terpenes such as α-pinene with H2O2 with minimal rearrangement of the epoxide. Pyridine is also critical to suppress isomerisation of the olefin substrate (in case of nerol, geraniol). The reaction can be directed towards selective single or double epoxidation, or in one step towards the rearranged product (e.g. from linalool to the ring-closure product linalool oxide).

  在吡啶作为助催化剂的存在下，CH 3 ReO 3以最小的环氧基重排催化H 2 O 2对萜烯（如α-pine烯）的环氧化。吡啶对于抑制烯烃底物的异构化也是至关重要的（如果是神经醇，香叶醇）。该反应可以针对选择性的单或双环氧化，或在一步中针对重排的产物（例如从芳樟醇到闭环产物芳樟醇氧化物）。
• Large pore bifunctional titanium–aluminosilicates: the inorganic non-enzymatic version of the epoxidase conversion of linalool to cyclic ethers
  作者：A. Corma、M. Iglesias、F. Sánchez

  DOI：10.1039/c39950001635

  日期：——

  Bifunctional aluminosilicate catalysts containing framework Ti are prepared, with two different topologies and pore sizes; these samples contain both acid and oxidizing catalytic sites and are highly selective for carrying out multistep reactions with selectivities close to those obtained with epoxidases, this is shown to occur for the oxidation of linalool to cyclic hydroxy ethers.

  含框架钛的双功能铝硅酸盐催化剂被制备，具有两种不同的拓扑结构和孔径；这些样品同时包含酸性和氧化催化位点，并且在进行多步反应时具有很高的选择性，其选择性接近于用环氧化酶获得的选择性，这在芳樟醇氧化为环状羟基醚的过程中得到了验证。
• Oxidation of α-hydroxy containing monoterpenes using titanium silicate catalysts: comments on regioselectivity and the role of acidity
  作者：Lee J. Schofield、Owain J. Kerton、Paul McMorn、Donald Bethell、Simon Ellwood、Graham J. Hutchings

  DOI：10.1039/b201724p

  日期：——

  The regioselective epoxidation of monoterpenes in the liquid phase has been studied using the titanosilicates TS-1 and TiAlβ. A range of oxidants (hydrogen peroxide, tert-butyl hydroperoxide and urea–hydrogen peroxide complex) have been studied in detail. The allylic alcohols linalool and geraniol have been studied alongside the non-allylic alcohol citronellol and the diene dihydromyrcene to help determine

  区域选择性 环氧化 的 单萜已使用钛硅酸盐TS-1和TiAlβ研究了液相中的。一系列氧化剂（过氧化氢， 叔丁基过氧化氢 和 尿素–过氧化氢复合体）已进行了详细研究。烯丙醇芳樟醇和香叶醇 已与非烯丙醇香茅醇和二烯二氢月桂烯一起研究，以帮助确定 羟基 在这些反应中。 二氢月桂烯 在较富电子的双键处被选择性地环氧化，无论 催化剂–氧化剂–溶剂系统。 香叶醇 可以接受盟友的协助 环氧化 与TS-1 –丙酮–过氧化氢 和TiAlβ–乙腈–尿素–过氧化氢。与TiAlβ–过氧化氢–甲醇，反应表明在转化过程中有一个诱导期 香叶醇 这被认为是自催化去除钛中钛的特征。 催化剂框架。的反应香茅醇 表明去除钛完全是由于存在烯丙基 酒精部分。最后，环氧化 的 芳樟醇以及随后的原位转换环氧化物研究了呋喃氧化物和吡喃氧化物。认为呋喃氧化物和吡喃氧化物的比例部分归因于其孔的几何形状和布朗斯台德酸度。催化剂。
• Catalytic homogeneous oxidation of monoterpenes and cyclooctene with hydrogen peroxide in the presence of sandwich-type tungstophosphates [M4(H2O)2(PW9O34)2]n−, M = CoII, MnII and FeIII
  作者：Isabel C.M.S. Santos、José A.F. Gamelas、Tiago A.G. Duarte、Mário M.Q. Simões、M. Graça P.M.S. Neves、José A.S. Cavaleiro、Ana M.V. Cavaleiro

  DOI：10.1016/j.molcata.2016.10.021

  日期：2017.1

  7-double bond for Mn4(PW9)2, affording 6,7-epoxide at 82% selectivity. Linalyl acetate 1,2-epoxide was the major product with 51% and 77% selectivity for Co4(PW9)2 and Fe4(PW9)2, respectively. Oxidation of carveol occurred with very good conversions in the presence of Mn4(PW9)2, Co4(PW9)2 and Fe4(PW9)2, yielding carvone and carveol 1,2-epoxide in similar amounts. Oxidation of cis-cyclooctene gave only the

  研究了夹心钨磷酸盐B-α-[M 4（H 2 O）2（PW 9 O 34）2 ] n-（M = Co II，Mn II，Fe III）的四丁基铵盐在（- ）的氧化中的催化效率R）-（+）-柠檬烯，香叶醇，芳樟醇，乙酸芳樟酯，香芹酚和顺式-环辛烯与过氧化氢的乙腈溶液。（R的氧化）-（+）-柠檬烯得到柠檬烯-1,2-二醇作为主要产物。芳樟醇的环氧化反应优先发生在取代度更高的6,7-双键上，相应的6,7-环氧化物进一步反应，通过分子内环化反应生成呋喃-和吡喃氧化物。乙酸芳樟酯的氧化优先发生在Mn 4（PW 9）2的更取代的6,7-双键处，以82％的选择性提供6,7-环氧。乙酸芳基酯1,2-环氧化物是主要产物，对Co 4（PW 9）2和Fe 4（PW 9）2的选择性分别为51％和77％。在锰的存在下，香芹酚的氧化转化率很高4（PW 9）2，Co 4（PW 9）2和Fe 4（PW 9）2产生类似量的香芹酮和香芹酚1
• Actinidia arguta: volatile compounds in fruit and flowers
  作者：Adam J Matich、Harry Young、John M Allen、Mindy Y Wang、Simon Fielder、Mark A McNeilage、Elspeth A MacRae

  DOI：10.1016/s0031-9422(03)00142-0

  日期：2003.6

  More than 240 compounds were detected when the volatile components of the flowers and the fruit from several Actinidia arguta genotypes were investigated. Around 60-70 different compounds were extracted from individual tissues of each genotype. Two different methods of volatile sampling (headspace and solvent) favoured different classes of compounds, dependent upon their volatilities and solubilities

  在对几种猕猴桃基因型的花和果实的挥发性成分进行研究时，检测到 240 多种化合物。从每个基因型的个体组织中提取了大约 60-70 种不同的化合物。两种不同的挥发性取样方法（顶空和溶剂）有利于不同类别的化合物，这取决于它们在花或果实基质中的挥发性和溶解度。从花中提取的化合物主要包括芳樟醇衍生物，包括丁香醛 (12a-d) 和醇 (13a-d)、2,6-二甲基-6-羟基辛基-2,7-二烯醛 (8)、8-羟基芳樟醇 (9 )、倍半萜烯和苯化合物，它们被认为是苯丙氨酸和酪氨酸的代谢物。水果样品的提取物中含有一些单萜，但以丁酸乙酯、己酸乙酯、2-甲基丁酸酯和2-甲基丙酸酯，由醛类己醛和己-E2-烯醛组成。还检测到了许多未鉴定的化合物，其中 8 种来自花的密切相关，它们要么是一种化合物的异构体，要么是两种或两种以上密切相关的化合物。这是关于猕猴桃中存在一系列芳樟醇衍生物的首次报告。

表征谱图