3-hydroxy-2-phenylsulphinylprop-1-ene | 63067-91-4

• 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: 3-hydroxy-2-phenylsulphinylprop-1-ene
• 英文别名: 2-(Phenylsulfinyl)-2-propenyl Alcohol；2-(benzenesulfinyl)prop-2-en-1-ol
• CAS: 63067-91-4
• 化学式: C₉H₁₀O₂S
• 分子量: 182.243
• InChiKey: NNJDUWFCNIBURD-UHFFFAOYSA-N

物化性质

• 沸点：
  411.3±28.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  3-hydroxy-2-phenylsulphinylprop-1-ene 在 氢氧化钾 、 lithium bromide 作用下， 以 乙醚 、 丙酮 为溶剂， 反应 1.5h， 生成 3-bromo-2-phenylsulfinyl-1-propene
  参考文献：
  名称：

  Khan, M. Akram; Al-Saleh, Balkis, Journal of Chemical Research, Miniprint, 1989, # 2, p. 320 - 333

  摘要：

  DOI：
• 作为产物：
  描述：

  3-(苯基亚磺酰)丙腈 在 水 作用下， 以 丙酮 为溶剂， 反应 60.0h， 生成 3-hydroxy-2-phenylsulphinylprop-1-ene
  参考文献：
  名称：

  通过亚硫酸分子内和分子间加成到炔烃中合成烯基亚砜

  摘要：

  通过在140℃下热解ω-（叔丁基亚磺酰基）炔烃形成的炔基-ω-亚磺酸，在区域特异性地环化成2-亚甲基硫代环烷烃1-氧化物；以此方式未形成2-亚甲基噻吨-1-氧化物。通过加热二叔丁基亚砜而获得的2-甲基丙烷-2-磺酸，被区域选择性地加入到辛基-1-炔中，主要生成2-叔丁基亚磺酰基辛基-1-烯，后者本身会热分解为二辛烯基亚砜的混合物。通过链烷磺酸-二烷基硫的相互转化。通过1-氰基-2-烷基（或芳基）亚磺酰基乙烷的热分解可方便地生成苯甲磺酸，甲磺酸和乙氧基羰基甲磺酸，将它们在分子间加成至选择性地生成未活化和活化的炔烃中，从而以良好的产率得到链烯基亚砜。

  DOI：

  10.1039/p19810002106

文献信息

• Reagents for rapid peptide synthesis
  申请人：Research Corporation Technologies, Inc.

  公开号：US05221754A1

  公开（公告）日：1993-06-22

  This invention relates to compounds of the formula: ##STR1## wherein R is an electron withdrawing group; R.sub.1 is H or COZ; X.sub.1 and X.sub.2 are independently H, lower alkyl, aryl, aryl lower-alkyl or polystyrene or R and X.sub.1 taken together with the carbon atoms to which they are attached form a ring containing from 4 to 15 ring carbon atoms and may contain up to 2 heteroatoms, wherein the heteroatoms are O, S, or N; and Z is an amino acid residue, a peptide residue or a leaving group. The compounds of the present invention are adaptable as blocking or protecting groups for an amine composition useful in peptide synthesis. The present invention is also directed to a method of protecting an amino group of an organic molecule during a reaction which modifies a portion of the molecule other than the protected amino group.

  本发明涉及以下结构的化合物：##STR1## 其中R是一个电子吸引基团；R.sub.1是H或COZ；X.sub.1和X.sub.2独立地是H、较低的烷基、芳基、芳基较低烷基或聚苯乙烯，或者R和X.sub.1与它们附着的碳原子一起形成一个含有4到15个环碳原子并且可能含有最多2个杂原子的环，其中杂原子是O、S或N；Z是氨基酸残基、肽残基或离去基团。本发明的化合物可用作肽合成中有用的胺组成部分的阻断或保护基团。本发明还涉及在修改分子的除受保护的氨基团之外的部分时保护有机分子的氨基团的方法。
• 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。
• First synthesis of (±)-pseudohygrophorone A12, an anti-fungal cyclohexenone derivative isolated from Hygrophorus abieticola
  作者：Yuzuki Yamamoto、Naoki Mori、Hidenori Watanabe、Hirosato Takikawa

  DOI：10.1016/j.tetlet.2018.08.027

  日期：2018.9

  Pseudohygrophorones A12 and B12 are cyclohexenone derivatives isolated from Hygrophorus abieticola (Basidiomycete) as anti-phytopathogenic compounds. In this study, the first synthesis of (±)-pseudohygrophorones A12 is reported, utilizing Michael–aldol cascade reaction for constructing the 3,3-dimethyl-2,4-dioxabicyclo[3.1.1]nonan-9-one skeleton and the diastereoselective addition of alkyllithium to

  假hygrophorones A 12和B 12是从松果Hygrophorus abieticola（Basidiomycete）分离得到的环己烯酮衍生物，作为抗植物病原性化合物。在这项研究中，报道了第一个合成（±）-假hygrophorones A 12的方法，利用迈克尔-奥尔多级联反应构建了3,3-二甲基-2,4-二氧杂双环[3.1.1] nonan-9-骨架和关键步骤是将烷基锂非对映选择性加成到一侧封端的酮中。
• The stereospecific synthesis ofcis andtrans 1-oxabicyclo[4,4,0]decanes and 9-methoxycarbonyl-1-oxabicyclo[4,3,0]nonanes
  作者：D. Neville Jones、M. Akram Khan、Sohail M. Mirza

  DOI：10.1016/s0040-4020(99)00532-3

  日期：1999.8

  The allylic sulphoxides1b and1e reacted with 1-pyrrolidinylcyclohexene and 2-ethoxycarbonyl cyclopentanone to yield the 2-substituted keto-sulphoxides10 and14 respectively, which on reduction followed by oxidation yielded in each case a mixture ofcis andtrans sulphones that were separated by column chromatography. Base induced cyclisation followed by reductive desulphurisation of the cyclised sulphones

  烯丙基亚砜1b和1e与1-吡咯烷基环己烯和2-乙氧羰基环戊酮反应，分别生成2-取代的酮亚砜10和14，在还原后进行氧化分别得到顺式和反式砜的混合物，将其分离通过柱色谱法。碱诱导的环化，然后对环化的砜进行还原性脱硫，得到了相应的双环化合物6、7、8和9，收率很高。
• 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.