(1S,4S)-4-methanesulfonyloxy-1-ethylhexyl methanesulfonate | 137151-99-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: (1S,4S)-4-methanesulfonyloxy-1-ethylhexyl methanesulfonate
• 英文别名: (S,S)-octane-3,6-diyl dimethanesulfonate；[(3S,6S)-6-methylsulfonyloxyoctan-3-yl] methanesulfonate
• CAS: 137151-99-6
• 化学式: C₁₀H₂₂O₆S₂
• 分子量: 302.413
• InChiKey: STDVEIAZYMGLSP-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1S,4S)-4-methanesulfonyloxy-1-ethylhexyl methanesulfonate 在 sodiumsulfide nonahydrate 作用下， 以 乙醇 为溶剂， 反应 22.0h， 以0.28 g的产率得到(2S,5S)-2,5-diethyltetrahydrothiophene
  参考文献：
  名称：

  Explorations into the Potential of Chiral Sulfonium Reagents to Effect Asymmetric Halonium Additions to Isolated Alkenes

  摘要：

  While methods for the racemic dihalogenation and halohydroxylation of alkenes have been known for decades, enantioselective variants of these processes remain elusive. Initial attempts were made to overcome this long-standing challenge by exploring the potential of chiral, crystalline, sulfur-derived halonium reagents to accomplish the asymmetric dichlorination and iodohydroxylation of 1,2-dihydronaphthalene. Asymmetric dichlorination of this substrate was achieved in 57% yield and 14% enantiomeric excess (ee), but asymmetric iodohydroxylation was much more successful, giving 67% yield and 63% ee. Thorough studies were made of these processes, including investigation of various chiral sulfide derivatives, their substrate scopes, and the reaction conditions.

  DOI：

  10.1055/s-0033-1338865
• 作为产物：
  描述：

  3-氧代戊酸甲酯 在 氢氧化钾 、 cat 、 氢气 、 sodium methylate 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 25.0 ℃ 、10.34 MPa 条件下， 反应 97.0h， 生成 (1S,4S)-4-methanesulfonyloxy-1-ethylhexyl methanesulfonate
  参考文献：
  名称：

  新的手性膦酸酯；合成，表征及其在不对称氢化反应中的用途

  摘要：

  我们描述了对映体纯的反式-2,5-二取代-1-苯基膦酸酯的实际合成，然后将其用于制备一系列新的C 2对称双-和C 3对称三（膦）配体。概述了用于膦合成的重要手性1,4-二醇中间体的通用三步路线。制备了带有新的膦配体的铑配合物，并显示出它们可作为对各种不饱和底物进行对映选择性氢化的有效催化剂前体。

  DOI：

  10.1016/s0957-4166(00)86109-1

文献信息

• Enantioselective Redox-Neutral Rh-Catalyzed Coupling of Terminal Alkynes with Carboxylic Acids Toward Branched Allylic Esters
  作者：Philipp Koschker、Matthias Kähny、Bernhard Breit

  DOI：10.1021/jacs.5b01131

  日期：2015.3.4

  We report on the first enantioselective variant of the atom-economic and redox-neutral coupling of carboxylic acids with terminal alkynes under rhodium catalysis utilizing the chiral, bidentate (R,R)-Cp-DIOP ligand. This represents the first example of this convenient asymmetric access to valuable branched allylic esters. The utility of this methodology is demonstrated by both a reaction performed on large scale and a short three-step synthesis of two naturally occurring gamma-butyrolactones. A stereochemical model explaining the observed absolute configuration of the products based on DFT calculations is given.
• A Catalytic Cycle for the Asymmetric Synthesis of Epoxides Using Sulfur Ylides
  作者：Jacques Zanardi、Catherine Leriverend、Dimitri Aubert、Karine Julienne、Patrick Metzner

  DOI：10.1021/jo015588m

  日期：2001.8.1