(R)-tert-butyl vinyl sulfoxide | 126494-93-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 亚砜
• 英文名称: (R)-tert-butyl vinyl sulfoxide
• 英文别名: 2-[(R)-ethenylsulfinyl]-2-methylpropane
• CAS: 126494-93-7
• 化学式: C₆H₁₂OS
• 分子量: 132.227
• InChiKey: RKIAVFMRPCYSHY-MRVPVSSYSA-N

物化性质

• 沸点：
  226.5±13.0 °C(Predicted)
• 密度：
  0.999±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(叔丁基二甲基硅氧基)-1-甲氧基乙烯 、 (R)-tert-butyl vinyl sulfoxide 在 zinc(II) chloride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 10.0h， 生成 、 methyl (4R)-4-[tert-butyl(dimethyl)silyl]oxy-4-tert-butylsulfanylbutanoate
  参考文献：
  名称：

  Enantioselective Additive Pummerer-Type Reaction in Chiral, Non-racemic Vinyl Sulfoxides Induced by O-Silylated Ketene Acetal.

  摘要：

  在四氢呋喃中催化量的氯化锌存在下，用 O-甲硅烷基化烯酮乙缩醛处理手性非外消旋乙烯基亚砜，产生对映选择性 Pummerer 型反应，得到相当大的产率的相应对映体富集的甲基 4-甲硅烷氧基- 78-82% ee 的 4-硫基丁酸酯。

  DOI：

  10.1248/cpb.44.892
• 作为产物：
  描述：

  2-(乙烯基硫代)-2-甲基-丙烷 在 双氧水 作用下， 生成 (R)-tert-butyl vinyl sulfoxide
  参考文献：
  名称：

  A new enzymatic enantioselective synthesis of dialkyl sulfoxides catalysed by monooxygenases

  摘要：

  氯过氧化物酶或环己酮单加氧酶催化下，许多二烷基硫醚被对映选择性氧化为光学活性亚砜。

  DOI：

  10.1039/a608352h

文献信息

• An efficient route to chiral t-butyl sulfoxides
  作者：F. Rebiere、H.B. Kagan

  DOI：10.1016/s0040-4039(01)80475-5

  日期：1989.1

  cyclic sulfite 2 of (S)-1,1-diphenyl-propane-1,2-diol 1 gave chiral sulfinates 3 or 4 with high regio- and stereoselectivities, by reaction with various organometallics. The chiral sulfinates were then transformed in almost quantitative yields into enantiomerically pure sulfoxides by addition of a second organometallic reagent.

  通过与各种有机金属反应，（S）-1,1-二苯基丙烷-1,2-二醇1的环状亚硫酸盐2得到具有高区域选择性和立体选择性的手性亚磺酸盐3或4。然后通过加入第二种有机金属试剂，以几乎定量的产率将手性亚磺酸盐转化为对映体纯的亚砜。
• A general route to enantiomerically pure sulfoxides from a chiral sulfite
  作者：F. Rebiere、O. Samuel、L. Ricard、H. B. Kagan

  DOI：10.1021/jo00021a008

  日期：1991.10

  Enantiomerically pure cyclic chiral sulfite (S)-7 (trans stereochemistry) has been easily obtained in two steps from (S)-ethyl lactate. This compound was found to react cleanly with many organometallics to give crystalline sulfinates with high regioselectivity (> 90:10). Addition of a second organometallic transforms the purified sulfinate in excellent yield into a chiral sulfoxide (100% ee) of predictable absolute configuration. The mechanism and scope of this approach are discussed. This method completes the various other methods of preparation of chiral sulfoxides and is especially convenient for the preparation of tert-butyl sulfoxides. Examples for the synthesis of many chiral tert-butyl sulfoxides are given. The case of chiral sulfites derived from a C2 diol or of a chiral monoalcohol is also proposed as a route to chiral sulfinates, and some promising preliminary results have been obtained. The general main routes to obtain chiral sulfoxides from sulfites are also discussed.
• REBIERE, F.;KAGAN, H. B., TETRAHEDRON LETT., 30,(1989) N8, C. 3659-3662
  作者：REBIERE, F.、KAGAN, H. B.

  DOI：——

  日期：——
• A new enzymatic enantioselective synthesis of dialkyl sulfoxides catalysed by monooxygenases
  作者：Stefano Colonna、Nicoletta Gaggero、Giacomo Carrea、Piero Pasta

  DOI：10.1039/a608352h

  日期：——

  Numerous dialkyl sulfides were enantioselectively oxidized to optically active sulfoxides catalysed by chloroperoxidase or cyclohexanone monooxygenase.

  氯过氧化物酶或环己酮单加氧酶催化下，许多二烷基硫醚被对映选择性氧化为光学活性亚砜。
• Enantioselective Additive Pummerer-Type Reaction in Chiral, Non-racemic Vinyl Sulfoxides Induced by O-Silylated Ketene Acetal.
  作者：Norio SHIBATA、Chino FUJIMORI、Shigekazu FUJITA、Yasuyuki KITA

  DOI：10.1248/cpb.44.892

  日期：——

  Treatment of chiral, non-racemic vinyl sulfoxides with O-silylated ketene acetal in the presence of a catalytic amount of zinc chloride in tetrahydrofuran resulted in an enantioselective Pummerer-type reaction, affording a considerable yield of the corresponding enantiomerically enriched methyl 4-siloxy-4-sulfenylbutyrate in 78-82% ee.

  在四氢呋喃中催化量的氯化锌存在下，用 O-甲硅烷基化烯酮乙缩醛处理手性非外消旋乙烯基亚砜，产生对映选择性 Pummerer 型反应，得到相当大的产率的相应对映体富集的甲基 4-甲硅烷氧基- 78-82% ee 的 4-硫基丁酸酯。