(S)-(E)-4-methyl-1-(phenylsulfonyl)-1-penten-3-ol | 132016-59-2

• 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)-(E)-4-methyl-1-(phenylsulfonyl)-1-penten-3-ol
• 英文别名: (S,E)-4-methyl-1-(phenylsulfonyl)pent-1-en-3-ol；(E,3S)-1-(benzenesulfonyl)-4-methylpent-1-en-3-ol
• CAS: 132016-59-2
• 化学式: C₁₂H₁₆O₃S
• 分子量: 240.323
• InChiKey: PEXSLQWTOBMNTD-IDVQTMNDSA-N

物化性质

• 沸点：
  428.6±37.0 °C(predicted)
• 密度：
  1.168±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  62.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-(E)-4-methyl-1-(phenylsulfonyl)-1-penten-3-ol 在 potassium fluoride 、 disodium hydrogenphosphate 、 sodium amalgam 、 正丁基锂 、 phosphorus pentoxide 作用下， 以 甲醇 、 乙醇 、 氯仿 为溶剂， 反应 6.5h， 生成 ethyl (3S,4S)-4-(methoxymethoxy)-3,5-dimethylhexanoate
  参考文献：
  名称：

  A new method for the iterative construction of enantiomerically pure polypropionate chains

  摘要：

  DOI：

  10.1021/jo00058a053
• 作为产物：
  描述：

  苯砜基甲基膦酸二乙酯 、 异戊醛 在 亚硝基苯 、 D-脯氨酸 、 三乙胺 、 lithium bromide 作用下， 以 乙腈 为溶剂， 反应 26.0h， 以49%的产率得到(S)-(E)-4-methyl-1-(phenylsulfonyl)-1-penten-3-ol
  参考文献：
  名称：

  氨基氧化Horner-Wadsworth-Emmons序列用于合成对映体富集的γ-官能化乙烯基砜

  摘要：

  已经开发了一种操作简单的方法，用于合成γ-羟基乙烯基砜，该方法使用基于脯氨酸的醛氨氧基化反应，然后再通过乙烯基砜形成霍纳-沃兹沃思-埃蒙斯烯化反应。高对映体纯度形成的加合物随后被转化为γ-叠氮基乙烯基砜，叠氮化物-炔烃点击化学使合成基于乙烯基砜的三唑成为潜在的非肽半胱氨酸蛋白酶抑制剂。

  DOI：

  10.1021/acs.joc.5b02556

文献信息

• An efficient preparation of optically active (E)-γ-hydroxy-α,β-unsaturated phenyl sulfones using lipase-mediated acylations
  作者：Esteban Domínguez、Juan Carlos Carretero、Alfonso Fernández-Mayoralas、Santiago Conde

  DOI：10.1016/s0040-4039(00)93455-5

  日期：1991.9

  (E)-gamma-Hydroxy-alpha,beta-unsaturated phenyl sulfones have been efficiently resolved via irreversible enzymatic acylation with lipase PS (pseudomonas cepacia) and vinyl acetate. This process has been applied to the synthesis of the aggregation pheromone (-)-(3S,4S)-4-methyl-3-heptanol.

  (E)-γ-羟基α,β-不饱和苯砜在双歧杆菌PS（双歧杆菌Cepacia）酶催作用以及乙酰醋酸二注射液的配合下，通过不可逆的酶促甲基化过程得到脱炔酮双键。此方法已被用于合成的聚合外ustedache，（-）-（3S,4S）—4-甲基-3-Heptanol。
• Flexible and stereoselective construction of polypropionate chains from enantiomerically pure γ-hydroxy-α,β-unsaturated sulfones
  作者：Esteban Domínguez、Juan C. Carretero

  DOI：10.1016/s0040-4020(01)90483-1

  日期：——

  the readily available enantiomerically pure γ-hydroxy vinyl sulfone 2 has been transformed, with complete control of the stereochemistry, into γ-hydroxy vinyl sulfones of polypropionate structure. The four stereotriads have been prepared by stereoselective additions of organometallics to the vinyl sulfone moiety and by stereoselective reduction of β-hydroxyketones. In a similar way, these triads are the

  按照同源序列，在完全控制立体化学的情况下，容易获得的对映体纯的γ-羟基乙烯基砜2已转化为聚丙烯酸酯结构的γ-羟基乙烯基砜。通过将有机金属化合物立体选择性地添加到乙烯基砜部分并通过立体选择性地还原β-羟基酮来制备了四种立体三单元组。以类似的方式，这些三重轴是用于立体选择性地引入第四连续的不对称中心的底物。
• Stereoselective approach to optically pure syn 2-amino alcohol derivatives
  作者：Jesús de Blas、Juan C. Carretero、Esteban Domínguez

  DOI：10.1016/s0040-4039(00)60741-4

  日期：1994.6

  A highly stereoselective procedure for the preparation of a variety of syn 2-amino alcohol derivatives from enantiopure E-γ-hydroxy-α,β-unsaturated phenyl sulfones is described. The method is based on an intramolecular carbamate cyclization, followed by functionalization at α-position by reaction of the sulfonyl carbanion with electrophiles, and subsequent elimination of the sulfonyl group.

  描述了从对映体纯的E-γ-羟基-α，β-不饱和苯基砜制备各种合成的2-氨基醇衍生物的高度立体选择性的方法。该方法基于分子内氨基甲酸酯环化，然后通过磺酰基碳负离子与亲电试剂的反应在α-位官能化，然后消除磺酰基。
• Lipase-catalyzed kinetic resolution of .gamma.-hydroxy phenyl sulfones
  作者：Juan C. Carretero、Esteban Dominguez

  DOI：10.1021/jo00040a028

  日期：1992.7

  Lipase PS (from Pseudomonas cepacia) catalyzed the enantioselective transesterification of racemic gamma-hydroxy-alpha,beta-unsaturated phenyl sulfones 1 and their alpha,beta-saturated derivatives 3 with vinyl acetate in an organic solvent (usually (i)Pr2O). Remarkably, in substrates 1 with (E)-stereochemistry, the enantioselectivity of the process was little influenced by the nature of the R chain. Hence, very high enantiomeric ratios (E greater-than-or-equal-to 45) were observed in substrates 1 bearing short (R = Me or Et), long (R = n-Cr6H13 or n-C10H21), bulky (R = (i)Pr), or functionalized R chains. The (R)-enantiomer was the fast-reacting enantiomer in all cases. Concerning the reactivity, the rate of the reaction decreased significantly with an increase in size or length of the R chain (reaction time for 50% conversion from 3.5 to 162 h). Less satisfactory enantioselectivities (E = 5-48) were obtained when the saturated substrates 3 were used instead of the corresponding alpha,beta-unsaturated alcohols 1.
• Control of diastereofacial selectivity in the nucleophilic epoxidation of γ-oxygenated-α,β-unsaturated sulphones
  作者：Richard F.W. Jackson、Stephen P. Standen、William Clegg

  DOI：10.1016/s0040-4039(00)92395-5

  日期：1991.9

  Epoxidation of gamma-oxygenated-alpha,beta-unsaturated sulphones 4-8 with lithium t-butyl hydroperoxide proceeds with moderate to high diastereoselectivity to give 2-phenylsulphonyl oxiranes 9-13. The sense of diastereoselectivity is dependent on the steric bulk of the alkyl substituent at the gamma-centre.