(S)-(E)-4-(phenylsulfonyl)-3-buten-2-ol | 132016-57-0

• 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-(phenylsulfonyl)-3-buten-2-ol
• 英文别名: (S,E)-4-(phenylsulfonyl)but-3-en-2-ol；(E)-(S)-[MeCH(OH)CHCHSO2Ph]；(E,2S)-4-(benzenesulfonyl)but-3-en-2-ol
• CAS: 132016-57-0
• 化学式: C₁₀H₁₂O₃S
• 分子量: 212.269
• InChiKey: JABFJGMKUVJZPC-FLOXNTQESA-N

物化性质

• 沸点：
  420.3±37.0 °C(Predicted)
• 密度：
  1.232±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 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：
  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-(phenylsulfonyl)-3-buten-2-ol 在 lithium t-butyl peroxide 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以56%的产率得到
  参考文献：
  名称：

  Control of diastereofacial selectivity in the nucleophilic epoxidation of γ-oxygenated-α,β-unsaturated sulphones

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(00)92395-5
• 作为产物：
  描述：

  (E)-1-benzenesulfonyl-1-buten-3-ol 在 lipase-PS (Pseudomonas cepacia) 、 molecular sives 4A 作用下， 以 异丙醚 为溶剂， 反应 5.5h， 以47%的产率得到[(E,2R)-4-(benzenesulfonyl)but-3-en-2-yl] acetate
  参考文献：
  名称：

  An efficient preparation of optically active (E)-γ-hydroxy-α,β-unsaturated phenyl sulfones using lipase-mediated acylations

  摘要：

  (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。

  DOI：

  10.1016/s0040-4039(00)93455-5

文献信息

• Aminooxylation Horner–Wadsworth–Emmons Sequence for the Synthesis of Enantioenriched γ-Functionalized Vinyl Sulfones
  作者：William Doherty、Paul Evans

  DOI：10.1021/acs.joc.5b02556

  日期：2016.2.19

  operationally simple protocol for the synthesis of γ-hydroxy vinyl sulfones has been developed using a proline-based aldehyde aminooxylation, followed by a vinyl sulfone forming Horner–Wadsworth–Emmons olefination. The adducts, formed in high enantiopurity, were subsequently converted to γ-azido vinyl sulfones, and azide–alkyne click chemistry enabled the synthesis of vinyl sulfone-based triazoles as potential

  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。
• Palladium-catalyzed asymmetric synthesis of allylic alcohols from unsymmetrical and symmetrical racemic allylic carbonates featuring C–O-bond formation and dynamic kinetic resolution
  作者：Hans-Joachim Gais、Oleg Bondarev、Ralf Hetzer

  DOI：10.1016/j.tetlet.2005.07.044

  日期：2005.9

  Described is the asymmetric synthesis of the allylic alcohols 11 (85% ee), 15 (99% ee), 17 (93% ee), 19 (61% ee), and 21 (69% ee) through a Pd-catalyzed reaction of the unsymmetrical carbonates rac-10, rac-12, rac-14, rac-16, rac-18, and rac-20, respectively, with KHCO3 and H2O in the presence of bisphosphane 6. Similarly the allylic alcohols 23 (99% ee) and 25 (97% ee) have been obtained from the symmetrical

  描述了通过Pd催化反应不对称合成烯丙醇11（85％ee），15（99％ee），17（93％ee），19（61％ee）和21（ee％）在双膦6存在下用KHCO 3和H 2 O分别分离不对称碳酸盐rac - 10，rac - 12，rac - 14，rac - 16，rac - 18和rac - 20。。类似地，分别从对称的碳酸盐rac - 22和rac - 24获得了烯丙醇23（ee为99％）和25（ee为97％）。所述的反应内消旋-biscarbonate 26用H 2 O和钯（0）/ 6醇，得到27（96％EE），将其转化到PG构建块32。不饱和bisphosphane 33在醇的合成显示36，37，和39类似的高选择性为6。醇的形成11，15和17涉及一种有效的动态动力学拆分。
• Iron-Mediated Allylic Substitution Reactions with Chirality Transfer. Stereochemistry of the Formation of Diastereo- and Enantiomerically Enriched Olefinic and Allylic Tetracarbonyl Iron Complexes
  作者：Dieter Enders、Bernd Jandeleit、Stefan von Berg、Gerhard Raabe、Jan Runsink

  DOI：10.1021/om010343l

  日期：2001.10.1

  15‘/‘ ‘ (Acc = CO2Me) (48% − quant.; de < 3−70%), each diastereomer in enantiopure form (Note: descriptors ‘ and ‘ ‘ denote major and minor diastereomer). Synthetically useful results were obtained for allylic ligands bearing a benzylic protecting group [(S)-6a and (S)-8] and using hexane or diethyl ether as solvent (14a‘/a‘ ‘:  quant., de = 70%; 15‘/‘ ‘:  75−88%, de = 10−16%). Complexes 14a‘/a‘ ‘ were

  由对映体合成（E）-构象烯丙基配体（S）-6a - f和（S）-8，在C（3）（烯丙基位置）带有离去基团和在C（1）带有电子受体取代基（S）-乳酸乙酯[（S）-1 ]。络合为Fe 2（CO）9（13），得到其（η的对映体混合物2 -烯烃）tetracarbonyliron（0）配合物14A '/一个' ' - ˚F '/ ˚F ''（受体基团，度Acc = SO2 Ph）和15 '/''（Acc = CO 2 Me）（48％-定量； de <3-70％），每个非对映异构体为对映纯形式（注： 描述符'和''表示主要和次要非对映异构体） 。对于带有苄基保护基[（S）-6a和（S）-8 ]的烯丙基配体，使用己烷或乙醚作为溶剂，可获得合成上有用的结果（14a '/ a ''：定量，de = 70％；15 '/''：75-88％，de = 10-16％）。配合物14a '/ a“”进行分级结晶，并通
• One-Step Palladium-Catalyzed Synthesis of Substituted Dihydrofurans from the Carbonate Derivatives of γ-Hydroxy-α,β-unsaturated Sulfones
  作者：José L. Garrido、Inés Alonso、Juan C. Carretero

  DOI：10.1021/jo981391r

  日期：1998.12.1

  The palladium-catalyzed nucleophilic allylic substitution of the carbonate derivatives of gamma-hydroxy-alpha,beta-unsaturated sulfones (2) with soft carbon nucleophiles such as malonates, beta-keto esters, 1,3-diketones, and alpha-sulfonyl ketones took place cleanly and with full regiocontrol (gamma-substitution). Typical optimized conditions are Pd-2(dba)(3) (5 mol %), dppe (20 mol %), molecular sieves, in toluene-THF at 100 degrees C. Unexpectedly, when beta-keto esters, 1,3-diketones, and alpha-sulfonyl ketones were used as nucleophiles a cascade process occurred, via initial gamma-regioselective allylic substitution and further intramolecular conjugate addition of the enol moiety to the alpha,beta-unsaturated sulfone, to give 2,3,4,5-tetrasubstituted dihydrofurans (13-25) in moderate to good yields. Moreover, the cyclization step is highly stereoselective giving predominantly or exclusively the 4,5-dihydrofuran of trans configuration. From readily available enantiopure (S)-2, this one-step procedure of synthesis of substituted dihydrofurans has been applied to the synthesis of enantiomerically pure tetrasubstituted tetrahydrofurans.
• 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.