S-2,4,6-triisopropylphenyl α-bromothiopropionate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: S-2,4,6-triisopropylphenyl α-bromothiopropionate
• 英文别名: S-2,4,6-triisopropylphenyl 2-bromopropanethioate；S-[2,4,6-tri(propan-2-yl)phenyl] 2-bromopropanethioate
• 化学式: C₁₈H₂₇BrOS
• 分子量: 371.382
• InChiKey: WUWZTTIBDXGOMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  S-2,4,6-triisopropylphenyl α-bromothiopropionate 在 sodium iodide 作用下， 以 丙酮 为溶剂， 以55%的产率得到S-2,4,6-triisopropylphenyl α-iodothiopropionate
  参考文献：
  名称：

  Direct Carbon−Carbon Bond Formation via Reductive Soft Enolization: A Kinetically Controlled syn-Aldol Addition of α-Halo Thioesters and Enolizable Aldehydes

  摘要：

  The direct addition of enolizable aldehydes and alpha-halo thioesters to produce beta-hydroxy thioesters enabled by reductive soft enolization is reported. The transformation is operationally simple and efficient and has the unusual feature of giving high syn-selectivity, which is the opposite of that produced for (thio)esters under conventional conditions. Moreover, excellent diastereoselectivity results when a chiral nonracemic alpha-hydroxy aldehyde derivative is used.

  DOI：

  10.1021/ja1057407
• 作为产物：
  描述：

  2,4,6-Triisopropylthiophenol 、 2-溴丙酰溴 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 以51%的产率得到S-2,4,6-triisopropylphenyl α-bromothiopropionate
  参考文献：
  名称：

  Direct Carbon−Carbon Bond Formation via Reductive Soft Enolization: A Kinetically Controlled syn-Aldol Addition of α-Halo Thioesters and Enolizable Aldehydes

  摘要：

  The direct addition of enolizable aldehydes and alpha-halo thioesters to produce beta-hydroxy thioesters enabled by reductive soft enolization is reported. The transformation is operationally simple and efficient and has the unusual feature of giving high syn-selectivity, which is the opposite of that produced for (thio)esters under conventional conditions. Moreover, excellent diastereoselectivity results when a chiral nonracemic alpha-hydroxy aldehyde derivative is used.

  DOI：

  10.1021/ja1057407

文献信息

• Reductive Mannich-type reaction using the composite reagents of phosphine and Lewis acid
  作者：Satoshi Kikuchi、Takayuki Kobayashi、Yukihiko Hashimoto

  DOI：10.1016/j.tetlet.2006.01.106

  日期：2006.3

  We found that the combination of Ph3P and TiCl4 was the excellent promoter for reductive Mannich-type reaction of S-2,4,6-triisopropylphenyl 2-bromopropanethioate with several imines and that the corresponding products were obtained in good yields with high anti-selectivity.

  我们发现，Ph 3 P和TiCl 4的组合是S -2,4,6-三异丙基苯基2-溴丙烷硫酸酯与几种亚胺的还原曼尼希型反应的极好促进剂，并以高收率和高收率获得了相应的产物。反选择性。
• Reductive Claisen-Type Condensation Promoted by the Combination of Phosphine and Lewis Acid
  作者：Yukihiko Hashimoto、Hiroyuki Konishi、Satoshi Kikuchi

  DOI：10.1055/s-2004-825580

  日期：——

  The Ph 3 P/TiCl 4 combination was found to be an effective promoter for the Claisen-type condensation of α-bromothioesters. Both in the case of self-condensation and crossed-type reactions, corresponding β-ketothioesters were obtained in good yields.

  发现Ph 3 P/TiCl 4 组合是α-溴硫酯的克莱森型缩合的有效促进剂。在自缩合和交叉型反应的情况下，相应的 β-酮硫酯都以良好的产率获得。
• Phosphine/Lewis Acid Mediated Reformatsky-type Reaction of α-Bromoketone or -Thioester Derivatives
  作者：Yukihiko Hashimoto、Satoshi Kikuchi

  DOI：10.1246/cl.2002.126

  日期：2002.2

  The combination of (o-tolyl)3P/TiCl4 effectively promoted the Reformatsky-type reaction of α–bromoketone or -thioester derivatives with various aldehydes, and the corresponding β–hydroxy carbonyl compounds were obtained in good yield with high diastereoselectivity.

  (邻甲苯基)3P/TiCl4 的组合有效地促进了 α-溴酮或硫代酯衍生物与各种醛的 Reformatsky 型反应，并以良好的收率和高非对映选择性获得了相应的 β-羟基羰基化合物。
• Direct Carbon−Carbon Bond Formation via Reductive Soft Enolization: A Kinetically Controlled <i>syn</i>-Aldol Addition of α-Halo Thioesters and Enolizable Aldehydes
  作者：Scott J. Sauer、Michelle R. Garnsey、Don M. Coltart

  DOI：10.1021/ja1057407

  日期：2010.10.13

  The direct addition of enolizable aldehydes and alpha-halo thioesters to produce beta-hydroxy thioesters enabled by reductive soft enolization is reported. The transformation is operationally simple and efficient and has the unusual feature of giving high syn-selectivity, which is the opposite of that produced for (thio)esters under conventional conditions. Moreover, excellent diastereoselectivity results when a chiral nonracemic alpha-hydroxy aldehyde derivative is used.