(S_S)-(+)-2-(p-Tolylsulfinyl)prop-2-en-1-ol | 234436-57-8

• 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_S)-(+)-2-(p-Tolylsulfinyl)prop-2-en-1-ol
• 英文别名: (S_S)-2-(p-tolylsulfinyl)prop-2-en-1-ol；(S)-(p-tolylsulfinyl)-1-propene-1-ol；2-[(S)-(4-methylphenyl)sulfinyl]prop-2-en-1-ol
• CAS: 234436-57-8
• 化学式: C₁₀H₁₂O₂S
• 分子量: 196.27
• InChiKey: NSDWNHLBKVSXHU-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  56.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S_S)-(+)-2-(p-Tolylsulfinyl)prop-2-en-1-ol 在 二(氰基苯)二氯化钯 tin(ll) chloride 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 12.0h， 生成 (1R)-4-(methylamino)-3-[(R)-(4-methylphenyl)sulfinyl]-1-pyridin-3-ylbutan-1-ol
  参考文献：
  名称：

  Studies on the diastereoselective allylation of aldehydes with enantiopure 2-sulfinylallyl building blocks

  摘要：

  A comparative study on the allylation of aldehydes with enantiopure (S-S)-2-(p-tolylsulfonyl)-prop-2-en-1-ol (S-S)-1a and the corresponding chloride (S-S)-1b under two different reaction systems is reported. In general, better yields were obtained from chloride (S-S)-1b, whereas higher diastereoinduction was observed from alcohol (S-S)-1a. The sense of diastereoinduction is the same in both systems and the stereochemistry of the major diastereomer has been determined. Moreover, the configurational stability of the sulfoxide group on the resulting sulfinyl homoallylic alcohols 3 has been proven in each reaction system. which demonstrates the efficiency of the sulfoxide group as chiral auxiliary in these allylation processes. Finally. as an example of the synthetic potential of the resulting adducts, a total synthesis of natural enantioenriched (S)-nicotine from sulfinylalcohol 3h is reported, (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00266-x
• 作为产物：
  描述：

  2-溴-2-丙烯-1-醇 、 (1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate 在 叔丁基锂 作用下， 生成 (S_S)-(+)-2-(p-Tolylsulfinyl)prop-2-en-1-ol
  参考文献：
  名称：

  Syntheses of Both Enantiomers of 1,7-Dioxaspiro[5.5]undecane: Pheromone Components of the Olive Fruit-Fly Dacus oleae from a New Chiral Intermediate, the (SS)-2-(p-Tolylsulfinyl)prop-2-en-1-ol

  摘要：

  1,7-二氧螺[5.5]十烷的两个对映体，橄榄果蝇 Dacus oleae 的信息素成分，已通过一个新的手性亚砜 (S S)-2-(对甲基苯基亚砜基)丙-2-烯-1-醇合成，主要步骤包括异构 Diels-Alder 反应、在硅胶柱上对消旋体进行色谱分离以及在雷尼镍上进行脱硫。

  DOI：

  10.1055/s-1999-3467

文献信息

• First synthesis of both enantiomers of pseudohygrophorone A12, an anti-fungal cyclohexenone derivative isolated from Hygrophorus abieticola
  作者：Yuzuki Yamamoto、Yusuke Ogura、Hidenori Watanabe、Hirosato Takikawa

  DOI：10.1016/j.tet.2019.130528

  日期：2019.9

  Pseudohygrophorone A12, a highly oxygenated cyclohexenone derivative isolated from Hygrophorus abieticola, exhibits anti-fungal activity against several phytopathogenic fungi and oomycete. The first synthesis of both enantiomers of pseudohygrophorones A12 was accomplished starting from an optically active sulfoxide. In our approach, the diastereoselective Michael−aldol cascade reaction was featured as the key step

  假hygrophorone A 12，一种从松果Hygrophorus abieticola分离的高度氧化的环己烯酮衍生物，对几种植物病原真菌和卵菌菌素均表现出抗真菌活性。从光学活性的亚砜开始，完成了首次合成的假高潮酮A 12对映异构体的合成。在我们的方法中，非对映选择性Michael-aldol级联反应是关键步骤。
• Diastereoselective Allylation of Aldehydes with an Enantiopure 2-Sulfinylallyl Halide under Environmentally Friendly Barbier-Type Conditions
  作者：Francesc Márquez、Amadeu Llebaria、Antonio Delgado

  DOI：10.1021/ol991412j

  日期：2000.2.1

  [reaction: see text] A simple, efficient, and diastereoselective zinc-promoted allylation of aldehydes with enantiopure (Ss)-3-chloro-2-(p-tolylsulfinyl)-1-propene [(Ss)-1] under aqueous Barbier conditions is described. The observed diastereoselectivity can be explained via an acyclic antiperiplanar transition state model.

  [反应：参见正文]在Barbier水溶液中，一种简单，有效且非对映选择性的锌促进醛与对映纯（Ss）-3-氯-2-（对甲苯基亚磺酰基）-1-丙烯[（Ss）-1]进行的烯丙基化烯丙基化反应条件描述。观察到的非对映选择性可以通过非环状反平面过渡态模型来解释。
• A Practical Route to Enantiopure, Highly Functionalized Seven-Membered Carbocycles and Tetrahydrofurans: Concise Synthesis of (+)-Nemorensic Acid
  作者：Fernando López、Luis Castedo、José L. Mascareñas

  DOI：10.1002/1521-3765(20020215)8:4<884::aid-chem884>3.0.co;2-q

  日期：2002.2.15

  those obtained from the sulfinyl precursors. Cleavage of the oxa-bridge on the desulfurated adducts yields highly functionalized seven-membered carbocyclic derivatives in enantiopure form. Alternative cleavage of the seven-membered carbocycle provides enantiomerically enriched tetrahydrofurans. We have exploited this reaction pathway for the synthesis of the naturally occurring enantiomer of nemorensic

  高度非对映选择性的热[5C + 2C]分子内吡喃-烯烃环加成反应可通过在烯烃的合适位置引入同手性对甲苯磺酰基进行。所得的加合物可以容易地脱硫，以得到光学活性的8-氧杂双环[3.2.1]辛烷衍生物。有趣的是，从亚磺酰基转变为磺酰亚胺基可允许逆转非对映选择性的方向，从而产生与由亚磺酰基前体获得的对映体的氧杂桥碳环系统。在脱硫的加合物上裂解氧杂桥，得到对映纯形式的高度官能化的七元碳环衍生物。七元碳环的替代裂解提供了对映体富集的四氢呋喃。
• Studies on the diastereoselective allylation of aldehydes with enantiopure 2-sulfinylallyl building blocks
  作者：Francesc Márquez、Amadeu Llebaria、Antonio Delgado

  DOI：10.1016/s0957-4166(01)00266-x

  日期：2001.7

  A comparative study on the allylation of aldehydes with enantiopure (S-S)-2-(p-tolylsulfonyl)-prop-2-en-1-ol (S-S)-1a and the corresponding chloride (S-S)-1b under two different reaction systems is reported. In general, better yields were obtained from chloride (S-S)-1b, whereas higher diastereoinduction was observed from alcohol (S-S)-1a. The sense of diastereoinduction is the same in both systems and the stereochemistry of the major diastereomer has been determined. Moreover, the configurational stability of the sulfoxide group on the resulting sulfinyl homoallylic alcohols 3 has been proven in each reaction system. which demonstrates the efficiency of the sulfoxide group as chiral auxiliary in these allylation processes. Finally. as an example of the synthetic potential of the resulting adducts, a total synthesis of natural enantioenriched (S)-nicotine from sulfinylalcohol 3h is reported, (C) 2001 Elsevier Science Ltd. All rights reserved.
• Syntheses of Both Enantiomers of 1,7-Dioxaspiro[5.5]undecane: Pheromone Components of the Olive Fruit-Fly Dacus oleae from a New Chiral Intermediate, the (SS)-2-(p-Tolylsulfinyl)prop-2-en-1-ol
  作者：Patricia Hayes、Christian Maignan

  DOI：10.1055/s-1999-3467

  日期：1999.5

  Both enantiomers of 1,7-dioxaspiro[5.5]undecane, the pheromone components of the olive fruit-fly Dacus oleae have been synthesized from a new chiral sulfoxide, (S S)-2-(p-tolylsulfinyl)prop-2-en-1-ol via hetero Diels-Alder reaction, chromatographic separation of the diastereomers on a silica gel column and desulfurization over Raney nickel as key steps.

  1,7-二氧螺[5.5]十烷的两个对映体，橄榄果蝇 Dacus oleae 的信息素成分，已通过一个新的手性亚砜 (S S)-2-(对甲基苯基亚砜基)丙-2-烯-1-醇合成，主要步骤包括异构 Diels-Alder 反应、在硅胶柱上对消旋体进行色谱分离以及在雷尼镍上进行脱硫。