ethyl 2-chloro-2-(phenylthio)ethanoate | 60178-25-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: ethyl 2-chloro-2-(phenylthio)ethanoate
• 英文别名: ethyl α-chloro-α-(phenylthio)acetate；chloro-phenylsulfanyl-acetic acid ethyl ester；Chlor-phenylmercapto-essigsaeure-aethylester；Acetic acid, chloro(phenylthio)-, ethyl ester；ethyl 2-chloro-2-phenylsulfanylacetate
• CAS: 60178-25-8
• 化学式: C₁₀H₁₁ClO₂S
• 分子量: 230.715
• InChiKey: FUYWNANDTINOCO-UHFFFAOYSA-N

物化性质

• 沸点：
  120 °C(Press: 1 Torr)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2-chloro-2-(phenylthio)ethanoate 以 乙腈 为溶剂， 以66%的产率得到Ethyl α-chloro-α-fluoro-α-(phenylthio)acetate
  参考文献：
  名称：

  Electrolytic Partial Fluorination of Organic Compounds. 17. Regiospecific Anodic Fluorination of Sulfides Bearing Electron-Withdrawing Substituents at the Position .alpha. to the Sulfur Atom

  摘要：

  Regiospecific monofluorination of various sulfides bearing electron-withdrawing substituents, cyano, ester, acyl, amino, and phosphonate groups,at their alpha-positions was successfully carried out by the anodic oxidation of the sulfides in Et(3)N . 3HF/MeCN using an undivided cell. Fluorine was introduced at the position alpha to the sulfur atom selectively. Fluorination of alpha-(phenylthio)-substituted cyclic carbonyl compounds was also successful. Furthermore, anodic alpha,alpha-difluorination of ethyl alpha-(phenylthio)acetate was also successfully carried out although a large amount of electricity was required.

  DOI：

  10.1021/jo00116a037
• 作为产物：
  描述：

  苯硫基乙酸 在 二硫化碳 、 水 、 溴 、 silver(l) oxide 作用下， 生成 ethyl 2-chloro-2-(phenylthio)ethanoate
  参考文献：
  名称：

  Pummerer, Chemische Berichte, 1909, vol. 42, p. 2279

  摘要：

  DOI：

文献信息

• Facile stereoselective synthesis of cis- and trans-3-alkoxyazetidin-2-ones
  作者：Aman Bhalla、Paloth Venugopalan、Shamsher S. Bari

  DOI：10.1016/j.tet.2006.06.062

  日期：2006.8

  A highly stereoselective synthesis of cis- and trans-3-alkoxy-3-phenyl/benzylthioazetidin-2-ones is described. The reaction of α-chlorosulfide-β-lactams with various alcohols catalyzed by a Lewis acid such as ZnCl2 in the presence of molecular sieves (3–4 Å) leads to cis-3-alkoxy-3-phenyl/benzylthio-β-lactams whereas treatment of potassium 2-alkoxy-2-phenylthioethanoate with appropriate Schiff's base

  描述了顺式和反式-3-烷氧基-3-苯基/苄基硫代氮杂环丁烷-2-酮的高度立体选择性的合成。在分子筛（3-4Å）存在下，路易斯酸（如ZnCl 2）催化α-氯硫化物-β-内酰胺与各种醇的反应，导致顺式-3-烷氧基-3-苯基/苄硫基-β-内酰胺，而在三乙胺存在下使用POCl 3用适当的席夫氏碱处理2-烷氧基-2-苯基硫代乙酸钾盐会导致反式-3-烷氧基-3-苯基硫氮杂环丁烷-2-酮的形成。
• Chemoenzymatic Approaches to the Montanine Alkaloids:  A Total Synthesis of (+)-Brunsvigine
  作者：Martin G. Banwell、Okanya J. Kokas、Anthony C. Willis

  DOI：10.1021/ol071344y

  日期：2007.8.1

  available and enzymatically derived cis-1,2-dihydrocatechols 3a and 3b have been elaborated over 17 steps, including a novel radical addition/elimination sequence, into the enantiomer, (+)-1, of the montanine alkaloid brunsvigine [(-)-1].

  易得且酶促衍生的顺式1,2-二氢邻苯二酚3a和3b历经17个步骤，包括向褐煤碱生物碱[（- ）-1]。
• Synthesis of oxacyclic carboxylic esters through ring closure of α-alkoxy ester free radicals
  作者：Lucie D.M. Lolkema、Henk Hiemstra、Al Ayachi Al Ghouch、W. Nico Speckamp

  DOI：10.1016/0040-4039(91)80366-e

  日期：1991.3

  Cyclizations of 1-methyoxycarbonyl-2-oxa-5-hexenyl (and related) radical intermediates, generated from phenylthio precursors, proceed in good yields and mainly lead to substituted 2-tetrahydrofurancarboxylic esters.

  由苯硫基前体生成的1-甲氧基羰基-2-氧杂-5-己烯基（及相关）自由基中间体的环化反应，收率很高，主要产生取代的2-四氢呋喃羧酸酯。
• Cationic polar cycloaddition with chloromethyl phenyl sulfides
  作者：Y. Tamura、K. Ishiyama、Y. Mizuki、H. Maeda、H. Ishibashi

  DOI：10.1016/s0040-4039(01)82017-7

  日期：1981.1

  Chloromethyl phenyl sulfides 3 underwent [4+ +2] type polar cyclo-additions with styrene, trans-stilbene, and phenylacetylene in the presence of stannic chloride to afford the thiochroman 4, 5 and thiochromen derivatives 6. Under the same reaction conditions, N-allyl-α-chloro-α-(phenylthio)acetamide (7) gave the intramolecular cycloaddition product 8.

  在氯化锡的存在下，与苯乙烯，反式苯乙烯和苯乙炔进行氯甲基苯基硫化物3的[4 + +2]型极性环加成反应，得到硫代铬烷4、5和硫代色素衍生物6。在相同的反应条件下，N -烯丙基-α-氯-α-（苯硫基）乙酰胺（7）得到分子内环加成产物8。
• A novel and convenient synthesis of bis[arylthio]methanes
  作者：Malcolm M. Campbell、Veerappa B. Jigajinni、Keith A. MacLean、Richard H. Wightman

  DOI：10.1016/s0040-4039(00)78674-6

  日期：1980.1

  Bis[arylthio]methanes are produced in high yield on treatment of aryl chloromethyl sulphides with neutral alumina.

  用中性氧化铝处理芳基氯甲基硫化物可以高产率生产双[芳硫基]甲烷。