1-ethoxy-1-(trimethylsilyloxy)-2,2-(ethylenedithio)ethene | 182417-47-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二硫杂环戊烷
• 英文名称: 1-ethoxy-1-(trimethylsilyloxy)-2,2-(ethylenedithio)ethene
• 英文别名: ([1,3]dithiolan-2-ylidene-ethoxymethoxy)trimethylsilane；1-ethoxy-2,2-(ethylenedithio)-1-trimethylsiloxyethane；1-ethoxy-2,2-(ethylenedithio)-1-trimethylsiloxyethene；2-[ethoxy(trimethylsiloxy)methylene]-1,3-dithiolane；[1,3-Dithiolan-2-ylidene(ethoxy)methoxy]-trimethylsilane
• CAS: 182417-47-6
• 化学式: C₉H₁₈O₂S₂Si
• 分子量: 250.458
• InChiKey: WGHZYIZJPQIGPS-UHFFFAOYSA-N

物化性质

• 沸点：
  262.1±40.0 °C(Predicted)
• 密度：
  1.100±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.48
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  69.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-ethoxy-1-(trimethylsilyloxy)-2,2-(ethylenedithio)ethene 在 三氟化硼乙醚 、 potassium carbonate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 (2S,3S)-3-Amino-2-(2-ethoxycarbonyl-[1,3]dithiolan-2-yl)-pyrrolidine-1-carboxylic acid benzyl ester
  参考文献：
  名称：

  Design and synthesis of spiro-cyclopentenyl and spiro--dithiolanyl substituted pyrrolidine-5,5-trans-lactams as inhibitors of hepatitis C virus NS3/4A protease

  摘要：

  Using the pyrrolidine-5,5-trans-lactam template, we have designed small, neutral, mechanism-based inhibitors of hepatitis C NS3/4A protease. Compound 2b, with a spiro-cyclobutyl P1 substituent and an isopropyl carbonyl substituent at the lactam. nitrogen, has an IC50 value in the replicon cell-based assay of 3 muM. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00274-9
• 作为产物：
  描述：

  1,3-二硫烷-2-甲酸乙酯 、 三甲基氯硅烷 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以72%的产率得到1-ethoxy-1-(trimethylsilyloxy)-2,2-(ethylenedithio)ethene
  参考文献：
  名称：

  基于手性 1,3,2-Oxazaborolidin-5-one 促进的不对称醛醇反应和非对映选择性自由基还原的本质上对映纯素和反丙酸酯醛醇加合物的不同合成

  摘要：

  本质上，对映纯的合成和反丙醇醛加合物是使用一种新的策略不同地合成的，该策略利用高度对映选择性的 1,3,2-oxazaborolidin-5-one-促进的醛醇反应与衍生自乙基 2-溴的乙烯酮甲硅烷基缩醛丙酸盐和高度非对映选择性的自由基脱溴反应。这些程序提供的产率增加到可用于实际合成的水平。

  DOI：

  10.1246/bcsj.74.1485

文献信息

• A chiral oxazaborolidinone-promoted aldol reaction with a silyl ketene acetal from ethyl 1,3-dithiolane-2-carboxylate. Synthesis of acetate aldols in high enantiomeric purity
  作者：Syun-ichi Kiyooka、Mostofa Abu Hena

  DOI：10.1016/0957-4166(96)00265-0

  日期：1996.8

  Asymmetric synthesis of dithiolane aldols 3 was achieved in good yields by using silyl ketene acetal 1, derived from ethyl 1,3-dithiolane-2-carboxylate, in the chiral oxazaborolidinone (L-1 and D-2)-promoted aldol reaction and desulfurization of 3 resulted in production of acetate aldols 4 in high enantiomerc purity.

  在手性草并硼杂硼烷酮（L-1和D-2）促进的醛醇缩合反应和脱硫反应中，通过使用由1,3-二硫杂环戊酸-2-羧酸乙酯衍生的甲硅烷基乙烯酮缩醛1，可以高收率获得二硫杂环戊烷醛3的不对称合成。的3导致生产乙酸醛醇的4在高纯度enantiomerc。
• A short and efficient synthesis of N-Cbz-galantinic acid under promoter control on enantioselective acyclic stereoselection based on chiral oxazaborolidinone-promoted aldol reactions
  作者：Syun-ichi Kiyooka、Kazuki Goh、Yuri Nakamura、Hironori Takesue、Mostofa A Hena

  DOI：10.1016/s0040-4039(00)01124-2

  日期：2000.8

  An effective ‘promoter control’ on enantioselective acyclic stereoselection based on chiral oxazaborolidinone-promoted asymmetric aldol reactions has been found in the case of chiral N-protected α-amino aldehydes. An enantioselective synthesis of the title compound has been efficiently accomplished by using a sequence of the aldol reaction.

  在手性N-保护的α-氨基醛的情况下，已经发现基于手性氧杂氮杂硼烷酮促进的不对称醛醇缩合反应的对映选择性无环立体选择的有效“促进剂控制” 。通过使用醛醇缩合反应的序列，已经有效地完成了标题化合物的对映选择性合成。
• Enantioselective acyclic stereoselection under catalyst control. 2.1 Asymmetric synthesis of syn- and anti-1,3-diols incorporating an acetate equivalent by the chiral oxazaborolidinone-catalyzed aldol reaction
  作者：Syun-ichi Kiyooka、Takafumi Yamaguchi、Hirofumi Maeda、Haruhide Kira、Mostofa Abu Hena、Michio Horiike

  DOI：10.1016/s0040-4039(97)00701-6

  日期：1997.5

  The chiral oxazaborolidinone-catalysed aldol reaction of a silyl ketene acetal involving a dithiolane moiety with β-silyloxy aldehyde resulted in the production of syn- and anti-1,3-diols with complete stereoselection by the choice of the stereochemistry of the catalyst. This reaction is an elegant example of enantioselective acyclic stereoselection under catalyst control.

  含二硫杂环戊烷部分的甲硅烷基乙烯酮缩醛与β-甲硅烷氧基醛的手性草并氮杂硼烷二酮催化的羟醛缩醛反应，通过选择催化剂的立体化学，可以完全立体选择合成顺式和反式-1,3-二醇。该反应是在催化剂控制下对映选择性无环立体选择的一个很好的例子。
• Enantioselective synthesis of a key intermediate aldehyde toward the polyene macrolide filipin III, based on a chiral oxazaborolidinone-promoted asymmetric aldol reaction
  作者：Syun-ichi Kiyooka、Mostofa A. Hena、Fumitaka Goto

  DOI：10.1016/s0957-4166(99)00278-5

  日期：1999.7

  A versatile preparation of an enantiopure aldehyde useful for the asymmetric total synthesis of filipin III was developed using a chiral oxazaborolidinone-promoted asymmetric aldol reaction with a dithiolane silyl nucleophile. The sign and magnitude of the specific rotation of the aldehyde, (4R,5R)-2,2-dimethyl-5-formyl-4-pentyl-1,3-dioxane, were reconfirmed.

  使用与二硫杂环戊烷甲硅烷基亲核试剂的手性草并氮杂硼烷二酮促进的不对称醛醇缩合反应，开发了可用于菲林酯III的不对称全合成的对映体纯醛的通用制备方法。再次确认了醛（4 R，5 R）-2,2-二甲基-5-甲酰基-4-戊基-1,3-二恶烷的比旋度和大小。
• A Study Directed to the Asymmetric Synthesis of the Antineoplastic Macrolide Acutiphycin under Enantioselective Acyclic Stereoselection Based on Chiral Oxazaborolidinone-Promoted Asymmetic Aldol Reactions
  作者：Syun-ichi Kiyooka、Mostofa A. Hena

  DOI：10.1021/jo990342r

  日期：1999.7.1

  A shortening of the reaction path can be realized by using a series of the chiral oxazaborolidinone-promoted aldol reaction with respect to the practical synthesis of the (+)-acutiphycin seco acid derivative 5. The linear strategy is based on the utilization of five aldol reactions with a sequence of silyl nucleophiles, 7, 8, 35, 10, and 11, in the presence of stoichiometric amounts of the promoter, 1 or 2. The construction of the relative configuration between the stereogenic centers is diastereoselectively controlled by the stereochemistry of the promoter used in the enantioselective aldol reaction, which is nearly independent of that of the substrate (promoter control).