1-十四烯 | 1120-36-1

• 物质功能分类: 有机原料 - 烃类化合物及其衍生物 - 无环烃
• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 中文名称: 1-十四烯
• 中文别名: 1-十四碳烯；正十四烯
• 英文名称: 1-tetradecene
• 英文别名: tetradecene；tetradec-1-ene；n-tetradec-1-ene
• CAS: 1120-36-1
• 化学式: C₁₄H₂₈
• mdl: MFCD00008981
• 分子量: 196.376
• InChiKey: HFDVRLIODXPAHB-UHFFFAOYSA-N

物化性质

• 熔点：
  -13--11 °C (lit.)
• 沸点：
  251 °C (lit.)
• 密度：
  0.775 g/mL at 25 °C (lit.)
• 蒸气密度：
  6.8 (vs air)
• 闪点：
  240 °F
• LogP：
  7.08 at 20℃
• 物理描述：
  Watery liquid; colorless; mild pleasant odor. Floats on water. (USCG, 1999)
• 颜色/状态：
  COLORLESS LIQUID
• 气味：
  Mild, pleasant
• 溶解度：
  Water solubility= 4.0X10-4 mg/l at 25 °C (est)
• 蒸汽密度：
  6.78 (Air=1)
• 蒸汽压力：
  1.5X10-2 mm Hg at 25 °C
• 亨利常数：
  Henry's Law constant= 8.48 atm-cu m/mole at 25 °C (est)
• 自燃温度：
  455 °F (235 °C)
• 粘度：
  2.61 cu mm/s (Kinematic)
• 燃烧热：
  -17,600 Btu/lb = -9,779 Cal/g
• 汽化热：
  103 Btu/lb = 57.1 Cal/g
• 表面张力：
  25.0 dynes/cm @ 20 °C
• 折光率：
  INDEX OF REFRACTION: 1.4351 @ 20 °C/D
• 保留指数：
  1385 ;1388 ;1390 ;1390 ;1389.08 ;1389.35 ;1389.46 ;1389 ;1388 ;1388 ;1390 ;1390 ;1388 ;1387.9 ;1390 ;1390 ;1390 ;1389 ;1392 ;1392 ;1394 ;1391 ;1390 ;1383 ;1388 ;1394 ;1395 ;1389 ;1396 ;1400 ;1389 ;1389 ;1388 ;1394 ;1395 ;1389 ;1389 ;1392 ;1395 ;1412
• 稳定性/保质期：
  1. 在常温常压下保持稳定，应避免与氧化物接触。 2. 它存在于烟气中。

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  14
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.857
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

ADMET

代谢

在以1-十四烯为底物的矿物质-盐类碳水化合物培养基中培养的念珠菌。确定了1,2-二醇和Omega-不饱和脂肪酸。

CANDIDA GROWN IN MINERAL-SALTS HYDROCARBON MEDIUM USING 1-TETRADECENE AS SUBSTRATE. 1,2-DIOLS & OMEGA-UNSATURATED FATTY ACIDS DETERMINED.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 皮肤症状

干燥的皮肤。

Dry skin.

来源:ILO-WHO International Chemical Safety Cards (ICSCs)

毒理性

• 毒性数据

LC50 (大鼠) > 2,475 毫克/立方米/4小时

LC50 (rat) > 2,475 mg/m3/4h

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

毒理性

• 非人类毒性摘录

N-烯烃对热带假丝酵母的毒性与其在水介质中的溶解度有关。C12以上的长链N-烯烃通常不会抑制酵母的生长和呼吸。

THE TOXICITY OF N-ALKENES TOWARD CANDIDA TROPICALIS WAS RELATED TO THEIR SOLUBILITIES IN AN AQ MEDIUM. N-ALKENES LONGER THAN C12 GENERALLY DID NOT INHIBIT YEAST GROWTH AND RESPIRATION.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

饱和脂肪酸含偶数碳原子，由微生物从1-十二烯和1-十四烯合成。14-十五烯酸是由1-十四烯合成的。

SATURATED FATTY ACIDS CONTAINING EVEN NUMBERS OF CARBON ATOMS WERE SYNTHESIZED BY MICROBES FROM 1-DODECENE & 1-TETRADECDNE. 14-PENTADECENOIC ACID WAS SYNTHESIZED FROM 1-TETRADECENE.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

13-十四碳烯酸是从假单胞菌属铜绿假单胞菌菌株SOL 20的培养液中分离出来的，该菌株以1-十四碳烯作为唯一的碳源生长。当使用正十四烷作为生长底物时，没有产生这种酸。

13-TETRADECENOIC ACID WAS ISOLATED FROM CULTURE FLUID OF PSEUDOMONAS AERUGINOSA STRAIN SOL 20 GROWN ON 1-TETRADECENE AS THE SOLE CARBON SOURCE. THIS ACID WAS NOT PRODUCED WHEN N-TETRADECANE WAS THE GROWTH SUBSTRATE.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• TSCA：
  Yes
• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37
• WGK Germany：
  3
• 海关编码：
  2901299090
• 危险品运输编号：
  UN 1993 / PGIII
• 包装等级：
  III
• 危险类别：
  6.1
• 危险性防范说明：
  P501,P273,P331,P301+P310,P405
• 危险性描述：
  H304,H413
• 储存条件：
  请将容器密封保存，并存放在阴凉、干燥处。

SDS

Name:	1-Tetradecene 92% Material Safety Data Sheet
Synonym:	None Known
CAS:	1120-36-1

Section 1 - Chemical Product MSDS Name:1-Tetradecene 92% Material Safety Data Sheet
Synonym:None Known

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
1120-36-1	1-Tetradecene	92%	214-306-9

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

---

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

---

Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

---

Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas. Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

---

Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container. Avoid runoff into storm sewers and ditches which lead to waterways. Clean up spills immediately, observing precautions in the Protective Equipment section. Provide ventilation.

---

Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

---

Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 1120-36-1: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to minimize contact with skin.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Liquid
Color: clear, colorless
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 251 deg C @ 760.00mm Hg
Freezing/Melting Point: -13 deg C
Autoignition Temperature: 235 deg C ( 455.00 deg F)
Flash Point: 115 deg C ( 239.00 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: insoluble
Specific Gravity/Density: .7750g/cm3
Molecular Formula: C14H28
Molecular Weight: 196.38

---

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported.

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 1120-36-1 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1-Tetradecene - Not listed by ACGIH, IARC, or NTP.

---

Section 12 - ECOLOGICAL INFORMATION

---

Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

---

Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

---

Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 1120-36-1: No information available.
Canada
CAS# 1120-36-1 is listed on Canada's DSL List.
CAS# 1120-36-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 1120-36-1 is listed on the TSCA inventory.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

类别：易燃液体

可燃性危险特性：

• 明火、受热或遇氧化剂均可燃烧，燃烧时会排放刺激烟雾。

储运特性：

• 应存放在通风良好、低温干燥的库房内；
• 装卸时应轻拿轻放，并与氧化剂和酸类分开存放。

灭火剂：

• 可使用雾状水、泡沫、砂土、二氧化碳或1211灭火剂进行灭火。

反应信息

• 作为反应物：
  描述：

  1-十四烯 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 TBS-DHG催化剂 、 联硼酸新戊二醇酯 、 水 、 双氧水 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 52.0h， 以78%的产率得到1,2-十四烷二醇
  参考文献：
  名称：

  碳水化合物催化的对映选择性烯烃二硼化：增强 1,2-键合二硼配合物的反应活性

  摘要：

  烯烃的催化对映选择性二硼化是通过容易获得的碳水化合物衍生的催化剂来完成的。机理实验表明 1,2-键合二硼酸盐具有中间作用。

  DOI：

  10.1021/jacs.5b13174
• 作为产物：
  描述：

  反-7-十四(碳)烯 在 (^iPrDI)Co(η³-C₃H₅) 、 potassium tert-butylate 、 碘 、 potassium hydride 作用下， 以 四氢呋喃 、 甲醇 、 甲基叔丁基醚 为溶剂， 反应 44.25h， 生成 1-十四烯
  参考文献：
  名称：

  链式硼氢化和脱硼氢化反热力学烯烃异构化

  摘要：

  我们报道了一种脱硼氢反应工艺，该工艺可以与链式硼氢化反应相结合，产生内烯烃到末端烯烃的一锅、反热力学、短程或长程异构化。该脱硼氢反应通过包含亲核试剂活化、碘化和碱促进消除的序列发生。异构化在室温下进行，不需要氟化物碱，并且这种异构化的底物范围比我们之前报道的硅烷异构化的底物范围扩大了。

  DOI：

  10.1021/acs.orglett.1c03124
• 作为试剂：
  描述：

  2-异丙基-2-(N-吡咯烷基)乙腈 在 bis(1,5-cyclooctadiene)nickel (0) 氢氧化钾 、 1-十四烯 、 (S)-BINAP monoxide 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 27.0h， 生成 1-phenyl-4-methyl-2-pentene
  参考文献：
  名称：

  主题演讲文章。镍催化的烯丙基胺和硼酸的偶联

  摘要：

  烯丙胺在镍（0）催化剂而不是钯（0）催化剂存在下作为与硼酸交叉偶联的底物。芳基，乙烯基和甲基硼酸的作用良好。使用乙烯基衍生物，E异构体比Z偶联更有效-异构体和两者完全保留几何完整性。甲基化优选使用硼酸酯，例如2-甲基-1,3,2-苯并二恶唑硼酸酯或2-甲基-1,3,2-二氧杂硼烷，而不是甲基硼酸。反应的立体化学涉及烯丙基胺的净转化。区域选择性是配体的函数。通常，空间大的供体膦在取代度较低的位置促进新的C–C键形成。双齿配体，特别是1,1'-联萘-2,2'-双（二苯基次膦基）（BINAPO），可在取代度更高的烯丙基末端促进新的C–C键形成。与烯丙醇和与硼酸形成的酯相比，胺似乎是优选的伴侣，并具有更高的立体特异性。

  DOI：

  10.1039/p19950002083

文献信息

• MnO₂ as a terminal oxidant in Wacker oxidation of homoallyl alcohols and terminal olefins
  作者：Rodney A. Fernandes、Gujjula V. Ramakrishna、Venkati Bethi

  DOI：10.1039/d0ob01344g

  日期：——

  PdCl2/CrO3/HCl produced α,β-unsaturated ketones from homoallyl alcohols, the present method provided orthogonally the β-hydroxy-methyl ketones. No overoxidation or elimination of benzylic and/or β-hydroxy groups was observed. The method could be extended to the oxidation of simple terminal olefins as well, to methyl ketones, displaying its versatility. An application to the regioselective synthesis of gingerol is

  通过使用 Pd( II ) 催化剂和 MnO 2作为助氧化剂，已经开发了用于将较少探索的高烯丙醇的末端烯烃氧化成 β-羟基甲基酮的高效温和的反应条件。该方法反应条件温和，官能团相容性好，区域选择性和化学选择性高。而我们早期的 PdCl 2 /CrO 3系统/HCl由高烯丙醇产生α，β-不饱和酮，本方法正交提供β-羟基-甲基酮。没有观察到苄基和/或β-羟基的过度氧化或消除。该方法也可以扩展到简单末端烯烃的氧化，以及甲基酮的氧化，显示出其多功能性。展示了姜酚在区域选择性合成中的应用。
• Site-Selective Mono-Oxidation of 1,2-Bis(boronates)
  作者：Lu Yan、James P. Morken

  DOI：10.1021/acs.orglett.9b01204

  日期：2019.5.17

  Site-selective oxidation of vicinal bis(boronates) is accomplished through the use of trimethylamine N-oxide in 1-butanol solvent. The reaction occurs with good efficiency and selectivity across a range of substrates, providing 2-hydro-1-boronic esters which are shown to be versatile intermediates in the synthesis of chiral building blocks.

  通过在1-丁醇溶剂中使用三甲胺N-氧化物来完成邻位双（硼酸酯）的位点选择性氧化。该反应在一系列底物上以良好的效率和选择性进行，从而提供了2-氢-1-硼酸酯，该酯被证明是手性结构单元合成中的通用中间体。
• Comparative study of the vicinal functionalization of olefins with 2:1 bromide/bromate and iodide/iodate reagents
  作者：Manoj K. Agrawal、Subbarayappa Adimurthy、Bishwajit Ganguly、Pushpito K. Ghosh

  DOI：10.1016/j.tet.2009.01.095

  日期：2009.4

  halohydrins, halo methyl ethers, and halo acetates from olefins using 2:1 Br−/BrO3− and I−/IO3− reagents. In many cases both reagents afforded products selectively in high yields. The highest halogen atom efficiencies attained were 97% and 93% for Br−/BrO3− and I−/IO3−, respectively. Of the two reagents, I−/IO3− was established to be the preferred reagent for vicinal functionalization of linear alkenes and

  比较评价在邻位卤代醇，卤代甲基醚和卤代乙酸盐的合成由从使用2-烯烃：1溴- /的BrO 3 -和我- / IO 3 -试剂。在许多情况下，两种试剂都以高收率选择性地提供产物。得到最高卤素原子效率为97％和溴93％- /的BrO 3 -和我- / IO 3 - ，分别。这两个试剂，我- / IO 3 -已确定“丙烯酰胺”是用于直链烯烃的邻位官能化以及用于制备卤代乙酸酯的优选试剂。然而，只有溴- /的BrO 3 -是有效的邻位官能反式-二苯乙烯和查耳酮。
• Metal-Free-Catalyzed Synthesis of Allyl Nitriles via C_sp²–C_sp³ Coupling between Olefins and Azobis (Alkyl-carbonitrile)
  作者：Zhong-zhong Cao、Zhiwen Nie、Tonglin Yang、Miaodong Su、Hui Li、Wei-ping Luo、Qiang Liu、Can-Cheng Guo

  DOI：10.1021/acs.joc.9b03127

  日期：2020.3.6

  The metal-free-catalyzed synthesis of allyl nitriles from Csp2-Csp3 coupling between olefins and azobis was carried out. Key on this work was that the synthesis of allyl nitriles directly using olefin as a starting material was considered to be more efficient and economical than the alkyne, alkynyl carboxylic acid, or cinnamic acid used in previous works. Moreover, in this reaction, iodine served as

  由烯烃和偶氮二之间的Csp2-Csp3偶联进行了无金属催化的烯丙基腈的合成。这项工作的关键在于，直接使用烯烃作为起始原料合成烯丙基腈被认为比先前工作中使用的炔烃，炔基羧酸或肉桂酸更有效，更经济。此外，在该反应中，碘是唯一的促进剂，偶氮二bis是氰化试剂，N2是唯一的无毒副产物，可以避免利用金属催化剂和有毒的腈试剂并避免产生有毒废物。在最佳条件下，已经以良好至极好的收率合成了30多种所需产物，包括芳族和脂族腈。根据对照实验和文献数据，
• A Photoirradiative Phase-Vanishing Method: Efficient Generation of HBr from Alkanes and Molecular Bromine and Its Use for Subsequent Radical Addition to Terminal Alkenes
  作者：Hiroshi Matsubara、Ilhyong Ryu、Masaaki Tsukida、Daisuke Ishihara、Kenji Kuniyoshi

  DOI：10.1055/s-0030-1258482

  日期：2010.8

  phase-vanishing (PV) system comprised of an alkane, perfluorohexanes, and bromine was successfully combined by photoirradiation to efficiently generate hydrogen bromide, which underwent radical addition with 1-alkenes in the hydrocarbon layer to afford terminal bromides in high yields.

  由烷烃、全氟己烷和溴组成的三相相消失 (PV) 系统通过光照射成功结合以有效生成溴化氢，其与烃层中的 1-烯烃进行自由基加成，以高收率提供末端溴化物。

表征谱图