3,5-di-tert-butyl-4-methoxybenzene-1-sulfonyl chloride | 160252-94-8

• 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: 3,5-di-tert-butyl-4-methoxybenzene-1-sulfonyl chloride
• 英文别名: 3,5-Ditert-butyl-4-methoxybenzenesulfonyl chloride
• CAS: 160252-94-8
• 化学式: C₁₅H₂₃ClO₃S
• 分子量: 318.865
• InChiKey: MJOQQOWSOJPQLD-UHFFFAOYSA-N

物化性质

• 沸点：
  397.2±42.0 °C(Predicted)
• 密度：
  1.124±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  3,5-di-tert-butyl-4-methoxybenzene-1-sulfonyl chloride 在 sodium hydroxide 、 氢溴酸 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 0.5h， 生成 Nα-9-Fluorenylmethyloxycarbonyl-NG-4-methoxy-3,5-di-tert-butylbenzenesulphonyl-L-arginine
  参考文献：
  名称：

  Ali, Syed Safdar; Echner, Hartmut; Khan, Khalid Mohammed, Zeitschrift fur Naturforschung, B: Chemical Sciences, 1994, vol. 49, # 10, p. 1425 - 1433

  摘要：

  DOI：
• 作为产物：
  描述：

  3,5-bis(1,1-dimethylethyl)-4-methoxybenzenesulfonic acid 在 SOSl₂ 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以84%的产率得到3,5-di-tert-butyl-4-methoxybenzene-1-sulfonyl chloride
  参考文献：
  名称：

  Highly Diastereoselective Intermolecular β-Addition of Alkyl Radicals to Chiral 2-(Arylsulfinyl)-2-cycloalkenones

  摘要：

  The diastereoselectivity of intermolecular beta-addition of alkyl radicals to 2-(arylsulfinyl)-acycloalkenones depends largely upon the structure of the arylsulfinyl group. The reaction of a-cyclopentenones or 2-cyclohexenones having a sterically bulky arylsulfinyl group such as (3,5-di-tert-butyl-4-methoxyphenyl)-sulfinyl, (2,4,6-triisopropylphenyl)sulfinyl or (2,4,6-trimethylphenyl)-sulfinyl group gives 3-alkyl-2-(arylsulfinyl)-1-cyclopentanones or 3-alkyl-2-(arylsulfinyl)-1-cyclohexanones in excellent yields and with high diastereoselectivity. Both the X-ray crystallographic analysis and the NOE experiment in the H-1 NMR spectrum of (S)-2-[(2,4,6-triisopropylphenyl)-sulfinyl]- and (S)-2-[(2,4,6-trimethylphenyl)sulfinyl]-2-cyclopentenone reveal an effective shielding of one of the olefin faces at the beta-position by o-isopropyl and o-methyl groups. The addition of bidentate Lewis acids reverses the stereoselection through chelating the intermediates to give the addition products with high diastereoselectivity.

  DOI：

  10.1021/jo971093e

文献信息

• 6-Azabicyclo[3.2.1]octanes<i>via</i>Copper-Catalyzed Enantioselective Alkene Carboamination
  作者：Barbara J. Casavant、Azade S. Hosseini、Sherry R. Chemler

  DOI：10.1002/adsc.201400317

  日期：2014.8.11

  carboamination reaction that creates bridged heterocycles is reported herein. Two new rings are formed in this alkene carboamination reaction where N-sulfonyl-2-aryl-4-pentenamines are converted to 6-azabicyclo[3.2.1]octanes using [Ph-Box-Cu](OTf)2 or related catalysts in the presence of MnO2 as stoichiometric oxidant in moderate to good yields and generally excellent enantioselectivities. Two new stereocenters

  含氮杂环的桥联双环是生物活性有机小分子中的重要基序。本文报道了产生桥连杂环的对映选择性铜催化的烯烃碳氨基化反应。在该烯烃碳氨基化反应中形成两个新环，其中使用[Ph-Box-Cu]（OTf）2或相关催化剂，将N-磺酰基-2-芳基-4-戊烯胺转化为6-氮杂双环[3.2.1]辛烷。 MnO2作为化学计量氧化剂的存在，产率中等至良好，通常具有出色的对映选择性。反应中形成两个新的立体中心，而形成CC键的芳烃添加是净CH功能化。
• Mechanistic Analysis and Optimization of the Copper-Catalyzed Enantioselective Intramolecular Alkene Aminooxygenation
  作者：Monissa C. Paderes、Jerome B. Keister、Sherry R. Chemler

  DOI：10.1021/jo3023632

  日期：2013.1.18

  The catalytic asymmetric aminooxygenation of alkenes provides an efficient and straightforward approach to prepare chiral vicinal amino alcohols. We have reported a copper(II)-catalyzed enantioselective intramolecular alkene aminooxygenation, using (2,2,6,6-tetramethylpiperidin-1-yl)oxyl (TEMPO) as the oxygen source, which results in the synthesis of chiral indolines and pyrrolidines. Herein we disclose

  烯烃的催化不对称氨基氧化为制备手性邻氨基醇提供了一种有效且直接的方法。我们报道了铜 (II) 催化的对映选择性分子内烯烃氨基氧化，使用 (2,2,6,6-四甲基哌啶-1-基) 氧基 (TEMPO) 作为氧源，从而合成手性二氢吲哚和吡咯烷. 在此，我们公开了动力学研究表明反应在底物和 [Cu( R,R )-Ph-双(恶唑啉)]OTf 2催化剂中都是一级反应，而在 TEMPO 中是零级反应。此外，动力学同位素效应研究支持顺式-氨基铜化步骤，即在烯烃上添加 N-Cu，是限速步骤。如氘标记实验所示，随后形成碳自由基中间体和用 TEMPO 直接捕获碳自由基是 C-O 键形成的指示机制。配体屏幕显示双(恶唑啉) 上的C(4)-苯基取代是高不对称诱导的最佳选择。底物N-磺酰基的大小也影响反应的对映选择性。证明了制备规模的催化氨基氧化反应（克规模），并且在更大规模的反应中发现了对反应温度的意外依赖性。
• An improved and efficient procedure for the preparation of chiral sulfinates from sulfonyl chloride using triphenylphosphine
  作者：Yoshihiko Watanabe、Nobuyuki Mase、Moto-aki Tateyama、Takeshi Toru

  DOI：10.1016/s0957-4166(99)00066-x

  日期：1999.2

  An improved procedure of the Sharpless method for the preparation of chiral sulfinates by triphenylphosphine is described. A mixture of sulfonyl chlorides and diacetone-d-glucose or l-menthol in the presence of triethylamine was treated with triphenylphosphine in CH2Cl2 at 0°C to give the sulfinates in good yields.

  描述了通过三苯基膦制备手性亚磺酸盐的Sharpless方法的改进方法。在三乙胺存在下，将磺酰氯和双丙酮-d-葡萄糖或1-薄荷醇的混合物在0℃下在CH 2 Cl 2中用三苯基膦处理，以良好的产率得到亚磺酸盐。
• N-Fluoro-(3,5-di-tert-butyl-4-methoxy)benzenesulfonimide (NFBSI): A sterically demanding electrophilic fluorinating reagent for enantioselective fluorination
  作者：Hiroyuki Yasui、Takeshi Yamamoto、Takehisa Ishimaru、Takeo Fukuzumi、Etsuko Tokunaga、Kakehi Akikazu、Motoo Shiro、Norio Shibata

  DOI：10.1016/j.jfluchem.2011.01.005

  日期：2011.3

  We disclose here a novel electrophilic fluorinating reagent, N-fluoro-(3,5-di-tert-butyl-4-methoxy)benzenesulfonimide (NFBSI) as a sterically demanding analogue of popular fluorinating reagent, N-fluorobenzenesulfonmide (NFSI). NFBSI improves the enantioselectivity of the products as much as 18% for the cinchona alkaloid-catalyzed enantioselective fluorination of silylenol ether compared to the use

  我们在此公开了一种新颖的亲电氟化试剂，N-氟-（3,5-二叔丁基-4-甲氧基）苯磺酰亚胺（NFBSI），作为流行的氟化试剂，N-氟苯磺酰胺（NFSI）的空间需求类似物。与使用NFSI相比，NFBSI对金鸡纳生物碱催化的甲硅烷基醚的对映选择性氟化将产物的对映选择性提高了18％。
• Amphipathic sulfonamidobenzamides mimicking small antimicrobial marine natural products; investigation of antibacterial and anti-biofilm activity against antibiotic resistant clinical isolates
  作者：Elizaveta M. Igumnova、Ekaterina Mishchenko、Tor Haug、Hans-Matti Blencke、Johanna U. Ericson Sollid、Elizabeth G. Aarag Fredheim、Silje Lauksund、Klara Stensvåg、Morten B. Strøm

  DOI：10.1016/j.bmc.2018.08.032

  日期：2018.9

  There is an urgent need for novel antimicrobial agents to address the threat of bacterial resistance to modern society. We have used a structural motif found in antimicrobial marine hit compounds as a basis for synthesizing a library of antimicrobial sulfonamidobenzamide lead compounds. Potent in vitro antimicrobial activity against clinically relevant bacterial strains was demonstrated for two compounds, G6 and J18, with minimal inhibitory concentrations (MIC) of 4-16 mu g/ml against clinical methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant Enterococcus faecium (VRE). The two compounds G6 and J18, together with several other compounds of this library, also caused >= 90% eradication of pre-established biofilm of methicillin-resistant S. epidermidis (MRSE) at 40 mu g/ml. Using a luciferase assay, the mechanism of action of G6 was shown to resemble the biocide chlorhexidine by targeting the bacterial cell membrane.