(2-methyl[1,3]dithian-2-yl)acetic acid methyl ester | 73510-65-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2-methyl[1,3]dithian-2-yl)acetic acid methyl ester
• 英文别名: 2-Methyl-1,3-dithian-2-essigsaeure-methylester；2-methyl-[1,3]dithian-2-yl-acetic acid；Methyl 2-(2-methyl-1,3-dithian-2-yl)acetate
• CAS: 73510-65-3
• 化学式: C₈H₁₄O₂S₂
• 分子量: 206.33
• InChiKey: OFERBUQBWCVLQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  76.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2-methyl[1,3]dithian-2-yl)acetic acid methyl ester 在 sodium hydroxide 、 硫酸 作用下， 以 四氯化碳 为溶剂， 反应 10.5h， 生成 2-Methyl-1,3-dithian-2-essigsaeure-isopropylester
  参考文献：
  名称：

  Stahl, Ingfried; Manske, Rainer; Gosselck, Juergen, Chemische Berichte, 1980, vol. 113, # 2, p. 800 - 805

  摘要：

  DOI：
• 作为产物：
  描述：

  1,3-丙二硫醇 、 乙酰乙酸甲酯 在 三氟化硼乙醚 作用下， 以 氯仿 为溶剂， 生成 (2-methyl[1,3]dithian-2-yl)acetic acid methyl ester
  参考文献：
  名称：

  双功能环丙基试剂：7-E，9-Z三亚甲基苯甲酸B的全合成

  摘要：

  2-羟基甲基环丙基苯硫醚与亚磺酰基化-脱氢亚磺酰基化结合可以实现立体选择性和化学选择性的三孢子酸方法。

  DOI：

  10.1016/s0040-4039(00)88036-3

文献信息

• Chemoselective (Trans)thioacetalization of Carbonyl Compounds with a Reusable Lewis Acid-Surfactant-Combined Copper Bis(dodecyl sulfate) Catalyst in Water
  作者：Shiue-Shien Weng、Shen-Chun Chang、Tsuan-Hao Chang、Jong-Pyng Chyn、Shu-Wei Lee、Chao-An Lin、Fong-kuang Chen

  DOI：10.1055/s-0029-1218693

  日期：2010.5

  A Lewis acid-surfactant-combined copper bis(dodecyl sulfate) [Cu(DS)2] catalyst served as an efficient and reusable catalyst for the thioacetalization and transthioacetalization of carbonyl compounds and O,O-acetals in water at room temperature. Some of the major advantages of this procedure are high chemoselectivity, ease of operation and purification without any organic solvent, and high yields.

  路易斯酸表面活性剂复合物铜双(十二烷基硫酸) [Cu(DS)2] 催化剂是一种高效且可重复使用的催化剂，在室温下水中催化羰基化合物和O,O-缩醛的硫缩醛化和硫缩醛转移反应。该方法的主要优点包括高化学选择性、操作和纯化简便且无需任何有机溶剂、高产率。
• Assembly intermediates in polyketide biosynthesis: enantioselective syntheses of β-hydroxycarbonyl compounds
  作者：Christine Le Sann、Dulce M. Muñoz、Natalie Saunders、Thomas J. Simpson、David I. Smith、Florilène Soulas、Paul Watts、Christine L. Willis

  DOI：10.1039/b419492f

  日期：——

  versatile approach for the enantioselective synthesis of functionalised beta-hydroxy N-acetylcysteamine thiol esters has been developed which allows the facile incorporation of isotopic labels. It has been shown that a remarkable reversal of selectivity occurs in the titanium mediated aldol reaction of acyloxazolidinone using either (S)- or (R)-tert-butyldimethylsilyloxybutanal. The aldol products are valuable

  已经开发了用于对映选择性合成官能化的β-羟基N-乙酰半胱胺硫醇酯的通用方法，该方法允许容易地掺入同位素标记。已经显示出在使用（S）-或（R）-叔丁基二甲基甲硅烷基氧基丁醛的钛介导的恶唑烷酮的羟醛缩醛反应中，选择性的显着逆转发生。醛醇缩合产物是合成4-羟基-6-取代的δ-内酯的有价值的中间体。
• Catalytic carbon–sulfur bond formation by amphoteric vanadyl triflate: exploring with thia-Michael addition, thioacetalization, and transthioacetalization reactions
  作者：Chien-Tien Chen、Yow-Dzer Lin、Cheng-Yuan Liu

  DOI：10.1016/j.tet.2009.10.012

  日期：2009.12

  A series of thiols have been examined as protic nucleophiles for Michael-type additions to alpha,beta-unsaturated carbonyls as well as double nucleophilic condensations with aldehydes, ketones, and acetals catalyzed by amphoteric, water-tolerant vanadyl triflate under mild and neutral conditions. The newly developed C-S bond formation protocols were carried out smoothly in good to high yields in a highly chemoselective manner. (C) 2009 Elsevier Ltd. All rights reserved.
• The Determination of the Absolute Configurations of Diastereomers of (S)-Camphanoyl 3-Hydroxy-5-oxohexanoic Acid Derivatives by X-ray Crystallography
  作者：Kwai-Ming Cheung、Simon J. Coles、Michael B. Hursthouse、Neil I. Johnson、Peter M. Shoolingin - Jordan

  DOI：10.1002/1521-3773(20020402)41:7<1198::aid-anie1198>3.0.co;2-3

  日期：2002.4.2
• A general synthesis of homochiral β-hydroxy N-acetylcysteamine thioesters
  作者：Christine Le Sann、Thomas J. Simpson、David I. Smith、Paul Watts、Christine L. Willis

  DOI：10.1016/s0040-4039(99)00657-7

  日期：1999.5

  A convenient and efficient route for the enantioselective synthesis of functionalised B-hydroxy N-acetyicysteamine thioesters is described. The route allows the facile incorporation of vicinal C-13 labelling to produce intermediates required for biosynthetic studies on a wide range of polyketide metabolites, e.g. 6-MSA, monocerin, colletodiol and strobilurins. (C) 1999 Elsevier Science Ltd. All rights reserved.