phenyl 3-methoxypropyl sulfone | 307966-04-7

• 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: phenyl 3-methoxypropyl sulfone
• 英文别名: 3-methoxypropyl phenyl sulfone；PhSO2CH2CH2CH2OMe；3-Methoxypropylsulfonylbenzene；3-methoxypropylsulfonylbenzene
• CAS: 307966-04-7
• 化学式: C₁₀H₁₄O₃S
• 分子量: 214.285
• InChiKey: WNTWIGJBEBTZMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  phenyl 3-methoxypropyl sulfone 在 正丁基锂 作用下， 以 正己烷 、 正戊烷 为溶剂， 反应 24.0h， 以81%的产率得到Li[CH(SO2Ph)CH2CH2OMe]
  参考文献：
  名称：

  Lithiated γ-O-functionalized propyl phenyl sulfides and sulfones of the type Li[CH(SOxPh)CH2CH2OR] (x=0, 2). [Li{CH(SPh)CH2CH2Ot-Bu}(tmeda)] – A structurally characterized organolithium inner complex

  摘要：

  Lithiation of O-functionalized alkyl phenyl sulfides PhSCH2CH2CH2OR (R = Me, 1a; i-Pr, 1b; t-Bu, 1c; CPh3, 1d) with n-BuLi/tmeda in n-pentane resulted in the formation of alpha-and ortho-lithiated compounds [Li{CH(SPh)CH2CH2OR}(tmeda)] (alpha-2a-d) and [Li{o-C6H4SCH2CH2CH2OR)(tmeda)] o-2a-d), respectively, which has been proved by subsequent reaction with n-Bu3SnCl yielding the requisite stannylated gamma-OR-functionalized propyl phenyl sulfides n-Bu3SnCH(SPh)CH2CH2OR (alpha-3a-d) and n-Bu3Sn(o-C6H4SCH2CH2CH2OR) (o-3a-d). The a/ortho ratios were found to be dependent on the sterical demand of the substituent R. Stannylated alkyl phenyl sulfides alpha-3a-c were found to react with n-BuLi/tmeda and n-BuLi yielding the pure a-lithiated compounds alpha-2a-c and [Li{CH(SPh)CH2CH2OR}] (alpha-4a-b), respectively, as white to yellowish powders. Single-crystal X-ray diffraction analysis of [Li{CH(SPh) CH(2)CH(2)Ot- Bu}(tmeda)] (alpha-2c) exhibited a distorted tetrahedral coordination of lithium having a chelating tmeda ligand and a C, O coordinated organyl ligand. Thus, alpha-2c is a typical organolithium inner complex. Lithiation of O-functionalized alkyl phenyl sulfones PhSO2CH2CH2CH2OR (R = Me, 5a; i-Pr, 5b; CPh3, 5c) with n-BuLi resulted in the exclusive formation of the a-lithiated products Li[CH(SO2Ph)CH2CH2OR] (6a-c) that were found to react with n-Bu3SnCl yielding the requisite alpha-stannylated compounds n-Bu3SnCH(SO2Ph) CH2CH2OR (7a-c). The identities of all lithium and tin compounds have been unambiguously proved by NMR spectroscopy (1H, 13C, 119Sn). (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2009.05.035
• 作为产物：
  描述：

  3-(苯基硫代)-1-丙醇 在 氢氧化钾 、 双氧水 、 溶剂黄146 作用下， 以 二甲基亚砜 为溶剂， 反应 0.25h， 生成 phenyl 3-methoxypropyl sulfone
  参考文献：
  名称：

  负超共轭作为极性效应的一个组成部分的实验证据：α-磺酰基碳负离子形成的容易程度随 β-烷氧基取代基的取向而变化

  摘要：

  我们报告了强烈依赖几何的取代基效应的证据。R-氢的 HD 交换速率常数 (kexch)OR，在一组 19 ! - 已知的、固定的（或强烈优选的）H-CR-C 的烷氧基砜！- 或已测量扭转角。还测量了缺少烷氧基的相应模型化合物 (kexch) 模型的那些，从而提供比率 kN ) (kexch)OR/(kexch) 模型；如此获得的 kN 值范围超过 4 个数量级。我们表明，当考虑到空间和其他影响时，我们的观察结果与 log kN ) a + b cos 2 " (其中 a ) 1.70 ( 0.17 和 b ) 2.62 ( 0.20) 形式的方程一致。它是进一步表明，观察到的速率常数比与仅由感应效应和场效应组成的取代效应不一致，并且它们与第三种效应的额外存在完全一致，即负超共轭或广义异头效应，特别是初始碳负离子的部分负电荷向#CO/轨道的扭转角依赖性捐赠。这种效应在扭转角为 0 和 180

  DOI：

  10.1021/ja001320l

文献信息

• Halogens in γ-position enhance the acidity of alkyl aryl sulfones and alkane nitriles
  作者：M. Judka、A. Wojtasiewicz、W. Danikiewicz、M. Mąkosza

  DOI：10.1016/j.tet.2007.06.014

  日期：2007.9

  On the basis of measuring the rates of base-catalyzed deuterium exchange the pKa values of a series of 3-halopropyl aryl sulfones and 4-halobutyronitriles were estimated. It was shown that halogen substituents, although separated from the carbanionic site, exert a substantial carbanion stabilizing effect. These effects were rationalized by DFT calculations.

  在测量碱催化的氘交换速率的基础上，估算了一系列3-卤代丙基芳基砜和4-卤代丁腈的p K a值。结果表明，卤素取代基尽管与碳负离子位点分开，但发挥了相当大的碳负离子稳定作用。通过DFT计算合理化了这些影响。
• 10.1002/cssc.202400650
  作者：Xia, Xi-Rui、Du, Juan、Zhang, Yu-Xing、Jiang, Hong、Cheng, Wan-Min

  DOI：10.1002/cssc.202400650

  日期：——

  A photocatalyst-free aqueous-phase hydrosulfonylation of alkenes and alkynes with sulfonyl chlorides is described. The reaction proceeds efficiently under visible light irradiation in the presence of (TMS)3SiH and features mild conditions, broad substrate scope and excellent functional-group compatibility, offering a convenient and sustainable method for the synthesis of sulfones.

  描述了烯烃和炔烃与磺酰氯的无光催化剂水相加氢磺酰化反应。该反应在 （TMS）3SiH 存在下的可见光照射下高效进行，具有条件温和、底物范围广和出色的官能团相容性，为砜类的合成提供了一种方便且可持续的方法。
• [EN] PYRIDAZINONE DERIVATIVES USEFUL AS GLUCAN SYNTHASE INHIBITORS<br/>[FR] DÉRIVÉS DE PYRIDAZINONE UTILES EN TANT QU'INHIBITEURS DE SYNTHASE DE GLUCANE
  申请人：SCHERING CORP

  公开号：WO2008115381A1

  公开（公告）日：2008-09-25

  [EN] In its many embodiments, the present invention provides -substituted pyridazinone compounds as glucan synthase inhibitors, methods of preparing such compounds, pharmaceutical including one or more of such compounds, methods of preparing pharmaceutical formulations including one or more such compounds or one or more such compounds along with other antifungal agents, and methods of treatment, prevention, inhibition, or amelioration of one or more fungal infections associated with glucan synthase using such compounds or pharmaceutical compositions.
  [FR] L'invention concerne des composés de pyridazinone substitués en tant qu'inhibiteurs de synthase de glucane ; des procédés de préparation de tels composés, des produits pharmaceutiques comprenant un ou plusieurs de ces composés ; des procédés de préparation de formulations pharmaceutiques comprenant un ou plusieurs de ces composés seuls ou avec d'autres agents antifongiques ; et des procédés de traitement, de prévention, d'inhibition, ou d'amélioration d'une ou de plusieurs infections fongiques associées à une synthase de glucane utilisant de tels composés ou compositions pharmaceutiques.
• Experimental Evidence for Negative Hyperconjugation as a Component of the Polar Effect:  Variation of the Ease of α-Sulfonyl Carbanion Formation with the Orientation of a β-Alkoxy Substituent
  作者：James F. King、Rajendra Rathore、Zhenrong Guo、Manqing Li、Nicholas C. Payne

  DOI：10.1021/ja001320l

  日期：2000.10.1

  the incipient carbanion into the # C-O / orbital. This effect is largest with torsion angles of 0 and 180ϒ and at these torsion angles constitutes the major source of stabilization of the incipient carbanion by the ! -alkoxy group. The present observation of a torsion-angle-dependent substituent effect may be combined with the known adherence of the specific rate of R-sulfonyl carbanion formation to

  我们报告了强烈依赖几何的取代基效应的证据。R-氢的 HD 交换速率常数 (kexch)OR，在一组 19 ! - 已知的、固定的（或强烈优选的）H-CR-C 的烷氧基砜！- 或已测量扭转角。还测量了缺少烷氧基的相应模型化合物 (kexch) 模型的那些，从而提供比率 kN ) (kexch)OR/(kexch) 模型；如此获得的 kN 值范围超过 4 个数量级。我们表明，当考虑到空间和其他影响时，我们的观察结果与 log kN ) a + b cos 2 " (其中 a ) 1.70 ( 0.17 和 b ) 2.62 ( 0.20) 形式的方程一致。它是进一步表明，观察到的速率常数比与仅由感应效应和场效应组成的取代效应不一致，并且它们与第三种效应的额外存在完全一致，即负超共轭或广义异头效应，特别是初始碳负离子的部分负电荷向#CO/轨道的扭转角依赖性捐赠。这种效应在扭转角为 0 和 180
• Lithiated γ-O-functionalized propyl phenyl sulfides and sulfones of the type Li[CH(SOxPh)CH2CH2OR] (x=0, 2). [Li{CH(SPh)CH2CH2Ot-Bu}(tmeda)] – A structurally characterized organolithium inner complex
  作者：Michael Block、Matthias Linnert、Santiago Gómez-Ruiz、Dirk Steinborn

  DOI：10.1016/j.jorganchem.2009.05.035

  日期：2009.9

  Lithiation of O-functionalized alkyl phenyl sulfides PhSCH2CH2CH2OR (R = Me, 1a; i-Pr, 1b; t-Bu, 1c; CPh3, 1d) with n-BuLi/tmeda in n-pentane resulted in the formation of alpha-and ortho-lithiated compounds [LiCH(SPh)CH2CH2OR}(tmeda)] (alpha-2a-d) and [Lio-C6H4SCH2CH2CH2OR)(tmeda)] o-2a-d), respectively, which has been proved by subsequent reaction with n-Bu3SnCl yielding the requisite stannylated gamma-OR-functionalized propyl phenyl sulfides n-Bu3SnCH(SPh)CH2CH2OR (alpha-3a-d) and n-Bu3Sn(o-C6H4SCH2CH2CH2OR) (o-3a-d). The a/ortho ratios were found to be dependent on the sterical demand of the substituent R. Stannylated alkyl phenyl sulfides alpha-3a-c were found to react with n-BuLi/tmeda and n-BuLi yielding the pure a-lithiated compounds alpha-2a-c and [LiCH(SPh)CH2CH2OR}] (alpha-4a-b), respectively, as white to yellowish powders. Single-crystal X-ray diffraction analysis of [LiCH(SPh) CH(2)CH(2)Ot- Bu}(tmeda)] (alpha-2c) exhibited a distorted tetrahedral coordination of lithium having a chelating tmeda ligand and a C, O coordinated organyl ligand. Thus, alpha-2c is a typical organolithium inner complex. Lithiation of O-functionalized alkyl phenyl sulfones PhSO2CH2CH2CH2OR (R = Me, 5a; i-Pr, 5b; CPh3, 5c) with n-BuLi resulted in the exclusive formation of the a-lithiated products Li[CH(SO2Ph)CH2CH2OR] (6a-c) that were found to react with n-Bu3SnCl yielding the requisite alpha-stannylated compounds n-Bu3SnCH(SO2Ph) CH2CH2OR (7a-c). The identities of all lithium and tin compounds have been unambiguously proved by NMR spectroscopy (1H, 13C, 119Sn). (C) 2009 Elsevier B.V. All rights reserved.