syn-phenylthio 3-hydroxy-2-methyl-3-phenylpropanoate | 52411-61-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯硫酚酯
• 英文名称: syn-phenylthio 3-hydroxy-2-methyl-3-phenylpropanoate
• 英文别名: syn-S-phenyl 3-hydroxy-2-methyl-3-phenylpropanethioate；S-phenyl (2R,3R)-3-hydroxy-2-methyl-3-phenylpropanethioate
• CAS: 52411-61-7；91660-85-4；91660-87-6；121843-67-2；127471-69-6；138052-35-4；149402-99-3
• 化学式: C₁₆H₁₆O₂S
• 分子量: 272.368
• InChiKey: SYHUSISPSSCAFY-IUODEOHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  syn-phenylthio 3-hydroxy-2-methyl-3-phenylpropanoate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 syn-2-methyl-1-phenyl-1,3-propanediol
  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：

  苯甲醛 、 硫基丙酸苯酯 在 (S,S)-diazaborolidine 1 、 N,N-二异丙基乙胺 作用下， 生成 syn-phenylthio 3-hydroxy-2-methyl-3-phenylpropanoate
  参考文献：
  名称：

  烯醇盐组分的E / Z几何形状决定了手性二氮杂硼烷定向对映选择性醛醇缩合偶联醛组分的面选择

  摘要：

  烯醇盐几何形状对过渡态能量的影响的分析解释了使用手性二氮杂硼烷1作为试剂的乙酸酯和丙酸酯与醛的醛醇缩合反应的立体化学。

  DOI：

  10.1016/s0040-4039(00)60765-7

文献信息

• Ti-direct, powerful, stereoselective aldol-type additions of esters and thioesters to carbonyl compounds: application to the synthesis and evaluation of lactone analogs of jasmone perfumes
  作者：Ryohei Nagase、Noriaki Matsumoto、Kohei Hosomi、Takahiro Higashi、Syunsuke Funakoshi、Tomonori Misaki、Yoo Tanabe

  DOI：10.1039/b613544g

  日期：——

  thiophenyl esters or thioaryl esters with aldehydes and ketones was performed (total 46 examples). The present method is advantageous from atom-economical and cost-effective viewpoints; good to excellent yields, moderate to good syn-selectivity, substrate variations, reagent availability, and simple procedures. Utilizing the present reaction as the key step, an efficient short synthesis of three lactone

  进行了有效的TiCl（4）-Et（3）N或Bu（3）N促进的醛和酮与苯和硫代苯基酯或硫代芳基酯的醛醇型加成反应（共46例）。从原子经济和成本有效的观点来看，本发明的方法是有利的。从良好到优异的产率，中等到良好的同选选择性，底物变化，试剂的可获得性和简单的程序。利用本反应作为关键步骤，进行了茉莉花香精的三种内酯[2（5H）-呋喃酮]类似物的有效短合成。其中，顺式茉莉酮的内酯类似物具有独特的香料特性（tabac）。
• Powerful Stereoselective Aldol-type Additions of Phenyl and Phenylthio Esters with Aldehydes or Ketones Mediated by TiCl4/Amine Reagent
  作者：Yoo Tanabe、Noriaki Matsumoto、Syunsuke Funakoshi、Naoki Manta

  DOI：10.1055/s-2001-18780

  日期：——

  An efficient TiCl4/amine-promoted aldol-type addition of phenyl and phenylthio esters with aldehydes or ketones has been performed. The present method includes a practical merit from the green chemical viewpoint with regard to yields, variations of substrates, availability of reagents, and simple operations.

  进行了高效的TiCl4/胺促进的醛和酮与苯基及苯基硫酯的类似醇缩合的加成反应。该方法在绿色化学的视角下具有实际优势，包括产率、底物的多样性、试剂的可获得性以及操作的简单性。
• Organocatalytic Enantioselective Decarboxylative Aldol Reaction of Malonic Acid Half Thioesters with Aldehydes
  作者：Han Yong Bae、Jae Hun Sim、Ji-Woong Lee、Benjamin List、Choong Eui Song

  DOI：10.1002/anie.201306297

  日期：2013.11.11

  Copycat: A highly enantioselective biomimetic aldol reaction of malonic acid half thioesters with a variety of aldehydes affords optically active β‐hydroxy thioesters by employing the cinchona‐derived sulfonamide organocatalyst 1. The synthetic utility of this protocol was demonstrated by performing formal syntheses of the antidepressants (R)‐fluoxetine, (R)‐tomoxetine, (−)‐paroxetine, and (R)‐duloxetine

  模仿：丙二酸半硫酯与多种醛类的高度对映选择性仿生羟醛缩合反应，通过使用金鸡纳衍生的磺酰胺有机催化剂1，提供了光学活性的β-羟基硫代酯。通过执行抗抑郁药（R）-氟西汀，（R）-托莫西汀，（-）-帕罗西汀和（R）-度洛西汀的正式合成，证明了该方案的合成效用。
• Highly enantioselective and diastereoselective synthesis of β-amino acid esters and β-lactams from achiral esters and imines
  作者：E.J. Corey、Carl P. Decicco、Ronald C. Newbold

  DOI：10.1016/s0040-4039(00)92366-9

  日期：1991.9

  The reaction of S-tert-butyl thiopropionate with a number of N-benzyl or N-allyl aldimines (4) as promoted by the chiral diazaborolidine 1 and triethylamine afforded the β-amino acid esters 5 with high diastereoselectivity and enantioselectivity, providing a simple route to chiral β-lactams 6.

  S-叔丁基硫代丙酸酯与手性二氮杂硼烷1和三乙胺促进的许多N-苄基或N-烯丙基醛亚胺（4）的反应提供了具有高非对映选择性和对映选择性的β-氨基酸酯5合成手性β-内酰胺类的途径6。
• Stereoselective aldol condensations via alkenyloxy dialkoxyboranes: synthetic applications using thioesters
  作者：Cesare Gennari、Anna Bernardi、Silvia Cardani、Carlo Scolastico

  DOI：10.1016/0040-4020(84)85086-3

  日期：1984.1

  dialkoxyboranes derived from thioesters were found to be stereoconvergent: both Z and E enolates give syn aldol condensation products. The thioester additions to chiral aldehydes were studied. Internal selectivity (syn) was usually very high, while the relative stereoselectivity ranged from poor to good, depending on the specific aldehyde used. The aldol products were transformed to known compounds for correlation

  进行了详细的研究，将硫代丙酸苯基酯与亚乙基氯硼酸酯（ECB）和二异丙基乙胺（DPEA）进行烯醇化，随后对这些烯醇化物进行醇醛缩合反应。已发现衍生自硫酯的烯氧基二烷氧基硼烷是立体收敛的：Z和E的烯醇盐均生成顺式醇醛缩合产物。研究了手性醛中硫代酯的添加。内部选择性（syn）通常很高，而相对的立体选择性则根据所使用的特定醛的不同，从差到好。将醛醇缩合产物转化为已知化合物以进行相关。