S-phenyl α-chlorothioacetate | 24197-65-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯硫酚酯
• 英文名称: S-phenyl α-chlorothioacetate
• 英文别名: phenyl α-chlorothioacetate；S-phenyl-2-chlorothioacetate；S-phenyl chlorothioacetate；chloro-thioacetic acid S-phenyl ester；Chlor-thioessigsaeure-S-phenylester；Chloracetylmercapto-benzol；S-phenyl 2-chloroethanethioate
• CAS: 24197-65-7
• 化学式: C₈H₇ClOS
• 分子量: 186.662
• InChiKey: JOPPJXPSNQPPOK-UHFFFAOYSA-N

物化性质

• 熔点：
  45 °C
• 沸点：
  145 °C(Press: 0.7 Torr)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 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-phenyl α-chlorothioacetate 在 过氧乙酸 作用下， 以 氯仿 为溶剂， 反应 2.0h， 生成 Diethyl-1(phenylsulfinyl)vinyl-phosphat
  参考文献：
  名称：

  1-Thiovinyl phosphates and related materials

  摘要：

  DOI：

  10.1021/jo01276a037
• 作为产物：
  描述：

  苯硫酚 、 氯乙酰氯 在 silica gel 作用下， 反应 3.0h， 以87%的产率得到S-phenyl α-chlorothioacetate
  参考文献：
  名称：

  Silica-promoted facile synthesis of thioesters and thioethers: a highly efficient, reusable and environmentally safe solid support

  摘要：

  本文介绍了一种高效、温和且快速的室温下在硅胶表面介导的芳香族和脂肪族硫醇的酰化和烷基化方法。该方案允许在中性异相条件下保护硫醇，无需任何碱或路易斯酸，且作为促进剂的硅胶可循环使用多次而不会损失活性。

  DOI：

  10.1039/b925620b

文献信息

• Highly enantio- and diastereoselective boron aldol reactions of α-heterosubstituted thioacetates with aldehydes and silyl imines
  作者：Cesare Gennari、Anna Vulpetti、Gilles Pain

  DOI：10.1016/s0040-4020(97)00251-2

  日期：1997.4

  Boron enolates derived from α-heterosubstituted thioacetates and bearing menthone-derived chiral ligands react with aldehydes to give anti aldols with excellent diastero- and enantiocontrol. Boron enolates derived from tert-butyl α-halothioacetate and bearing menthone-derived chiral ligands react with imines with excellent diastero- and enantiocontrol to give syn α-halo-β-aminothioesters, which can

  衍生自α-杂取代硫代乙酸酯的硼烯酸酯和带有薄荷酮的手性配体与醛反应生成具有出色的非对映异构和对映异构控制的抗羟醛。衍生自α-卤代硫代乙酸叔丁酯并带有薄荷酮的手性配体的硼烯醇盐与亚胺反应，具有优异的非对映和对映体控制能力，可生成合成α-卤代-β-氨基硫酯，可通过在闭环过程中进行简单的闭环反应将其转化为相应的氮丙啶减少LAH。合成了抗菌素（+）-噻吩酚和（-）-氟苯尼考的​​关键前体。
• Direct carbon–carbon bond formation via soft enolization: aldol addition of α-halogenated thioesters
  作者：Julianne M. Yost、Rachel J. Alfie、Emily M. Tarsis、Insun Chong、Don M. Coltart

  DOI：10.1039/c0cc02345k

  日期：——

  α-Halo thioesters undergo soft enolization and syn-selective direct aldol addition to aldehydes in the presence of MgBr2·OEt2 and i-Pr2NEt to produce α-halo-β-hydroxy thioesters.

  α-卤代硫酯在MgBr2·OEt2和i-Pr2NEt存在下经历软烯醇化，并选择性地与醛进行顺式直接醇醛缩合，生成α-卤代-β-羟基硫酯。
• A kinetically controlled direct aldol addition of α-chloro thioesters via soft enolization
  作者：Rachel J. Alfie、Ngoc Truong、Julianne M. Yost、Don M. Coltart

  DOI：10.1016/j.tetlet.2016.11.010

  日期：2017.1

  direct aldol addition to aldehydes in the presence of MgBr2·OEt2 and i-Pr2NEt. At −78 °C the reaction proceeds in a kinetically controlled manner giving good diastereoselectivity. Significantly, the transformation is applicable to both enolizable and nonenolizable aldehydes. Moreover, excellent stereoselectivity results when a chiral nonracemic α-hydroxy aldehyde derivative is used. To our knowledge, this

  本文中我们报道了简单的α-氯代硫代酯在MgBr 2 ·OEt 2和i -Pr 2 NEt的存在下经历了软烯醇化反应，并直接向醛类中直接添加了羟醛。在-78°C，反应以动力学控制的方式进行，从而提供了良好的非对映选择性。明显地，该转化适用于可烯化和不可烯化的醛。此外，当使用手性非外消旋α-羟基醛衍生物时，可获得优异的立体选择性。据我们所知，这是基于动力学控制的基于软烯醇化的羟醛添加的首次报道。
• A simple synthesis of thiol esters from copper-I-mercaptides and acyl chlorides
  作者：Hans-Ulrich Reißig、Bernadette Scherer

  DOI：10.1016/s0040-4039(00)92877-6

  日期：1980.1

  Thiol esters are obtained from acyl chlorides and copper-I-mercaptides in excellent yields.

  从酰氯和铜-I-硫醇盐以优异的产率获得硫醇酯。
• Syntheses of pyrrolizidines and indolizidines from α,β-unsaturated sugar δ-lactones via Dieckmann condensation
  作者：Joanna Rabiczko、Zofia Urbańczyk-Lipkowska、Marek Chmielewski

  DOI：10.1016/s0040-4020(02)00005-4

  日期：2002.2

  Both N-methoxycarbonylmethyl- and N-methoxycarbonylethyl-derivatives of dihydroxy-(d)-homoproline were subjected to the intramolecular ester condensation to yield ketoesters of pyrrolizidine and indolizidine series, respectively. The former ketoester was transformed into derivative related to australine, while the latter were transformed into the natural lentiginosine as well as its 2-epi-, and 7-

  既Ñ -methoxycarbonylmethyl-和Ñ二羟基- （d）的-methoxycarbonylethyl衍生物-homoproline进行分子内酯缩合，得到分别为吡咯烷类和吲哚里系列酮酯。前者的酮酸酯被转化为与奥沙林有关的衍生物，而后者则被转化为天然的lentiginosine以及其2- epi-和7-hydroxy-2- epi-衍生物。