每周分子 | Molecule of the Week

Original ACS美国化学会 ACS美国化学会 2022-07-01

每周分子: ‍Trivertal

Molecule of the Week: Trivertal

Trivertal (2,4-二甲基-3-环己烯醛)是一种具有两个手性中心的有机分子，如其二维图像所示。该产品是一种常见的香料成分，含有95%的顺式对映体和5%的反式对映体。在香水行业，trivertal被称为“2,4-ivy carbaldehyde”。

商业上的trivertal可能被在环上不同位置具有甲基的异构体干扰。因此，熔点降低，并且混合物是液体。较纯的形式是熔点为85至90℃的固体。

在圣地亚哥举行的ACS美国化学年会上，加利福尼亚大学河滨分校的Guy Bertrand谈到了他的研究小组对稳定的环（烷基）（氨基）碳烯的研究，其中一种是由trivertal制备的。trivertal及相关化合物的二甲基环己烯结构可稳定卡宾，该卡宾可用作过渡金属催化剂的配体。

作为概念的证明，作者在gold（I）催化剂中使用了羧甲基将内部炔烃与仲二烷基胺进行加氢胺化反应，以高产率合成了复杂的喹啉衍生物。在他的演讲中，贝特朗讨论了他早些时候在一篇期刊文章中报道的反应机理。

Trivertal 信息速览

CAS 登记号	68039-49-6
分子式	C₉H₁₄O
摩尔质量	138.21 g/mol
外观	无色液体
沸点	196 ºC
水溶性	≈300 mg/L

Trivertal 危害信息

GHS 分类*: f易燃液体，分类4
H227—可燃液体
GHS 分类: 皮肤腐蚀/刺激，分类2
H315—引起皮肤刺激**
GHS 分类: 皮肤过敏，分类1
H317—可能引起皮肤过敏反应**
GHS 分类: 严重眼损伤/眼刺激，分类2A
H319—引起严重的眼睛刺激**

【关于每周分子】

自2001年以来，“每周分子”已成为广受欢迎的栏目。多数分子由读者推荐。每个结构都经由科学家审查，并以3-D和平面图像的形式显示，同时附有该分子简介。可以通过美国化学文摘社（CAS）提供的SciFinder中的CAS REGISTRY获取“每周分子”的更多信息。CAS REGISTRY中的每条物质信息都展示了物质的CAS登记号、索引名、通用名、商品名、书目信息等其他更多信息。发送邮件至motw@acs.org推荐您感兴趣的分子吧。

Sodium formaldehydesulfoxylate (SFS) is a long name for a rather small

Trivertal (2,4-dimethyl-3-cyclohexenecarboxaldehyde) is an organic molecule with two chiral centers, as shown in the 2-D image. The manufactured product, a common fragrance ingredient, contains 95% of the two cis enantiomers and 5% of the trans isomers. In the fragrance industry, trivertal is called “2,4-ivy carbaldehyde”.

Commercial trivertal is likely contaminated with isomers that have the methyl groups in different positions on the ring. Thus, the melting point is depressed, and the mixture is a liquid. Purer forms are solids with a melting range of 85 to 90 ºC.

At the recent ACS National Meeting in San Diego, Guy Bertrand of the University of California, Riverside, spoke about his research group’s studies of stable cyclic (alkyl)(amino)carbenes, one of which was prepared from trivertal. The dimethylcyclohexene structure of trivertal and related compounds stabilizes the carbene, which can be used as a ligand for transition-metal catalysts.

As a proof of concept, the authors used the carbenes in gold(I) catalysts for the hydroamination of internal alkynes with secondary dialkylamines to synthesize complex quinoline derivatives in high yields. In his presentation, Bertrand discussed the mechanisms of the reactions that he reported earlier in a journal article.

Trivertal fast facts

CAS Reg. No.	68039-49-6
Empirical formula	C₉H₁₄O
Molar mass	138.21 g/mol
Appearance	Colorless liquid
Boiling point	196 ºC
Water solubility	≈300 mg/L

Trivertal hazard information

GHS classification*: flammable liquids, category 4
H227—Combustible liquid
GHS classification: skin corrosion/irritation, category 2
H315—Causes skin irritation**
GHS classification: skin sensitization, category 1
H317—May cause an allergic skin reaction**
GHS classification: serious eye damage/eye irritation, category 2A
H319—Causes serious eye irritation**

*Globally Harmonized System of Classification and Labeling of Chemicals. Explanation of pictograms.

**Not all material safety data sheets contain these warnings.

About Molecule of the Week

MOTW has been a popular feature on ACS website since 2001. Many molecules are suggested by our website visitors. Every structure is reviewed by a scientist and displayed in 3-D and flat images with a brief description. Each week's molecule also links to a sample record from the CAS REGISTRY, which is searched using SciFinder. Each record displays the registry number, index name and synonyms, bibliographic information, and more. Send us a molecule suggestion at motw@acs.org.

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