1,3-ジチアン-2-カルボン酸 エチル
1,3-ジチアン-2-カルボン酸 エチル · エチル1,3-ジチアン-2-カルボキシラート · 1,3-ジチアン-2-カルボン酸エチル · 1,3-ジチアン-2-カルボン酸エチル, 98+% · エチル 1,3-ジチアン-2-カルボキシラート · Carboethoxy-1,3-dithiane · 2-Carboethoxy-1,3-dithiane · 2-Ethoxycarbonyl-1,3-dithiane
識別子と物理属性
| CAS No. | 20462-00-4 |
|---|---|
| 分子式 | C7H12O2S2 |
| 平均分子量 | 192.3 g/mol |
| 単同位体質量 | 192.02787162 g/mol |
| SMILES | CCOC(=O)C1SCCCS1 |
| InChIKey | ANEDZEVDORCLPM-UHFFFAOYSA-N |
| PubChem CID | 88552 |
| EC No. | 243-838-4 |
| DTXSID | DTXSID50174427 |
| 現地名 | 1,3-ジチアン-2-カルボン酸 エチル |
化学・物理的性質
| XLogP | 2.1 |
|---|---|
| 極性表面積 | 76.9 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 4 |
| 回転可能結合数 | 3 |
| 重原子数 | 11 |
| 形式電荷 | 0 |
| 複雑度 | 132 |
| 融点 | 19-21°C |
| 沸点 | 75-77 °C/0.2 mmHg (lit.) |
| 密度 | 1.22 g/mL at 25 °C (lit.) |
| 屈折率 | n20/D 1.539(lit.) |
| 引火点 | 130 °F |
| 貯蔵条件 | Keep in dark place,Sealed in dry,Room Temperature |
| 外観・状態 | clear liquid |
| 色 | Colorless to Light yellow to Light orange |
| 溶解度 | 水とわずかに混和する。 |
| BRN | 1424352 |
| InChI | InChI=1S/C7H12O2S2/c1-2-9-6(8)7-10-4-3-5-11-7/h7H,2-5H2,1H3 |
| InChIKey | ANEDZEVDORCLPM-UHFFFAOYSA-N |
| SMILES | S1CCCSC1C(OCC)=O |
| CAS データベース | 20462-00-4(CAS DataBase Reference) |
| NISTの化学物質情報 | Ethyl 1,3-dithiane-2-carboxylate(20462-00-4) |
化学的特性
clear yellowish liquid
安全性と法規制
| GHS 分類 | WarningH226 (100%): Flammable liquid and vapor [Warning Flammable liquids]P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 44 reports by companies from 2 notifications to the ECHA C&L Inventory. |
|---|---|
| 規制情報 | Chemical: 1,3-Dithiane-2-carboxylic acid, ethyl esterEthyl 1,3-dithiane-2-carboxylate: Does not have an individual approval but may be used under an appropriate group standard |
| Hazard Classes and Categories | Flam. Liq. 3 (100%) |
| F | 9-13 |
| 水環境危害等級（WGK） | 3 |
| 輸送番号（UN） | UN 3272 3/PG 3 |
| 税関コード | 29349990 |
| 危険文句（R） | 10 |
| 消防法 | 危-4-2-III |
| 安全措置（S） | 26-36/37/39-45 |
| 危険等級 | 3Flam. Liq. 3 |
| 包装等級 | III |
| 貯蔵分類 | 3 - Flammable liquids |
用途
使用
Ethyl 1,3-dithiane-2-carboxylate is used in syn-selective aldol reactions. It undergoes asymmetric oxidation to give trans bis-sulfoxide. It is used to generate carbanon, which finds application in the preparation of alfa- keto esters.
一般的な説明
Ethyl 1,3-dithiane-2-carboxylate is an α-keto acid equivalent and bulky equivalent of acetate. It participates in syn-selective aldol reactions. It can be prepared from the reaction of ethyl diethoxyacetate and 1,3-propanedithiol in the presence of BF3/Et2O. Asymmetric oxidation of ethyl 1,3-dithiane-2-carboxylate by Modena protocol has been reported to afford trans bis-sulfoxide in 60% yield. Carbanion from ethyl 1,3-dithiane-2-carboxylate may be employed for the preparation of α-keto esters.
製法・合成法
製造方法
To a solution of BF3. Et2O (57.5 mL, 0.454 mmol) in CHC13 (180 mL) heated at reflux was added dropwise, over a 1h period, a solution of 1,3-propanedithiol (22.7 mL, 0.227 mmol), followed by ethyl diethoxyacetate (40 g, 0.227 mmol) in CHCl3 (40 mL). The resulting mixture was heated for 30 minutes, and then cooled to rt. The cooled solution was washed 2 times with water, once with saturated aqueous NaHC03, and then re-washed with water. The combined organic phases were dried over MgS04, then evaporated to give 41 g (94%) of Ethyl 1,3-dithiane-2-carboxylate as a yellow oi. Yield: 94%
純化方法
Dissolve the ester in CHCl3, wash with aqueous K2CO3, twice with H2O, dry over MgSO4, filter, evaporate and distil the residue. [Eliel & Hartman J Org Chem 37 505 1972, Seebach Synthesis 1 17 1969, Beilstein 19/7 V 227.]