PhSO2CH2CH2CH2OiPr | 1190600-22-6

• 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: PhSO2CH2CH2CH2OiPr
• 英文别名: 3-Propan-2-yloxypropylsulfonylbenzene；3-propan-2-yloxypropylsulfonylbenzene
• CAS: 1190600-22-6
• 化学式: C₁₂H₁₈O₃S
• 分子量: 242.339
• InChiKey: IRAOLRVZSRRZPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  PhSO2CH2CH2CH2OiPr 在 正丁基锂 作用下， 以 正己烷 、 正戊烷 为溶剂， 反应 24.0h， 以79%的产率得到Li[CH(SO2Ph)CH2CH2OiPr]
  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：

  PhSCH2CH2CH2OiPr 在 双氧水 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 4.5h， 以88%的产率得到PhSO2CH2CH2CH2OiPr
  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

文献信息

• 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.