1,3-二-叔丁基-5-(氯甲基)苯 | 51625-14-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1,3-二-叔丁基-5-(氯甲基)苯
• 英文名称: 3,5-di-tert-butyl-benzoyl chloride
• 英文别名: 3,5-Di-tert-butylbenzyl chloride；3,5-di-tert-butyl-benzyl chloride；3,5-Di-tert-butyl-benzylchlorid；3,5,bis(1,1-dimethylethyl)chloromethylbenzene；3,5-Di-tert.-butylbenzylchlorid；1-Chloromethyl-3,5-bis(1,1-dimethylethyl)benzene；1,3-ditert-butyl-5-(chloromethyl)benzene
• CAS: 51625-14-0
• 化学式: C₁₅H₂₃Cl
• 分子量: 238.801
• InChiKey: UNRGFCVSCXJGCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,3-二-叔丁基-5-(氯甲基)苯 在 乌洛托品 作用下， 生成 3,5-双(叔丁基)苯甲醛
  参考文献：
  名称：

  Beets et al., Recueil des Travaux Chimiques des Pays-Bas, 1959, vol. 78, p. 570,582

  摘要：

  DOI：
• 作为产物：
  描述：

  3,5-二叔丁基苯甲酸 在 lithium aluminium tetrahydride 、 氯化亚砜 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 1,3-二-叔丁基-5-(氯甲基)苯
  参考文献：
  名称：

  Binding activity of substituted benzyl derivatives of chloronicotinyl insecticides to housefly-head membranes, and its relationship to insecticidal activity against the houseflyMusca domestica

  摘要：

  Variously substituted benzyl derivatives of chloronicotinyl insecticides were synthesized with a wide range of substituents including halogens, NO2, CN, CF, and small alkyl and alkoxy groups at the ortho, meta and para positions, as well as multiple-substituted benzyl analogues. Their binding activity to the alpha-bungarotoxin binding site in housefly (Musca domestica) head membrane preparations was measured. Among the compounds tested, the activity of the meta-CN derivative was the highest, being 20-100 times higher than those of imidacloprid, acetamiprid and nitenpyram. The synergized insecticidal activity against houseflies was also measured for selected compounds with the metabolic inhibitor, NIA16388 (propargyl propyl phenylphosphonate). For the nitromethylene analogues, including both benzyl and pyridylmethyl analogues, higher binding activity usually resulted in higher insecticidal activity. (C) 2000 Society of Chemical Industry.

  DOI：

  10.1002/1526-4998(200010)56:10<875::aid-ps220>3.0.co;2-a

文献信息

• Catalytic, Asymmetric Mannich-type Reactions of <i>N</i>-Acylimino Esters:  Reactivity, Diastereo- and Enantioselectivity, and Application to Synthesis of N-Acylated Amino Acid Derivatives
  作者：Shū Kobayashi、Ryosuke Matsubara、Yoshitaka Nakamura、Hidetoshi Kitagawa、Masaharu Sugiura

  DOI：10.1021/ja0281840

  日期：2003.3.1

  the synthesis of biologically important compounds were prepared using this novel catalytic asymmetric Mannich-type reaction, and at the same time, absolute and relative stereochemical assignments were made. In addition, it has been revealed that alkyl vinyl ethers reacted with N-acylimino esters in the presence of a catalytic amount of the Cu(II) catalyst to give the corresponding Mannich-type adducts

  在催化量的 Cu(OTf)(2)-手性二胺 3e 复合物存在下，N-酰基亚氨基酯与甲硅烷基烯醇醚反应以高产率和高对映选择性提供相应的曼尼希型加合物。各种衍生自酮的甲硅烷基烯醇醚以及酯和硫酯都能顺利反应。在α-取代的甲硅烷基烯醇醚（α-甲基或苄氧基）的反应中，以高产率和高非对映选择性和对映选择性获得了所需的顺式加合物。使用这种新型催化不对称曼尼希型反应制备了几种用于合成生物学上重要化合物的中间体，同时进行了绝对和相对立体化学分配。此外，已经表明，在催化量的 Cu(II) 催化剂存在下，烷基乙烯基醚与 N-酰基亚氨基酯反应，以高产率和高对映选择性得到相应的曼尼希型加合物。这是与烷基乙烯基醚催化不对称曼尼希型反应的第一个例子。基于Cu(II)-手性胺配合物的X射线晶体学分析、PM3计算和FT-IR分析等假设了反应机理、手性催化剂-亲电子配合物的结构以及这些催化不对称反应的过渡态. 最后，(1R,
• Catalytic Asymmetric Conjugate Addition of Simple Alkyl Thiols to α,β-Unsaturated <i>N</i>-Acylated Oxazolidin-2-ones with Bifunctional Catalysts
  作者：Yan Liu、Bingfeng Sun、Baomin Wang、Matthew Wakem、Li Deng

  DOI：10.1021/ja8085092

  日期：2009.1.21

  In this communication, we describe an unprecedented highly enantioselective catalytic conjugate addition of simple alkyl thiols to alpha,beta-unsaturated N-acylated oxazolidin-2-ones catalyzed by acid-base bifunctional catalysis. This reaction provides a useful catalytic method for the synthesis of optically active chiral sulfur compounds that are otherwise difficult to prepare by asymmetric catalysis

  在这篇通讯中，我们描述了一种前所未有的高度对映选择性催化共轭加成，在酸碱双功能催化的催化下，简单的烷基硫醇与 α,β-不饱和 N-酰化 oxazolidin-2-ones 进行了加成。该反应为合成光学活性手性硫化合物提供了一种有用的催化方法，否则这些化合物很难通过不对称催化制备。该反应的成功发展源于一项发现，即在适当修饰后，在 6' 位带有硫脲官能团的金鸡纳生物碱可以为不对称共轭加成提供高效催化。
• Spontaneous Assembly of Rotaxanes from a Primary Amine, Crown Ether and Electrophile
  作者：Stephen D. P. Fielden、David A. Leigh、Charlie T. McTernan、Borja Pérez-Saavedra、Iñigo J. Vitorica-Yrezabal

  DOI：10.1021/jacs.8b03394

  日期：2018.5.16

  the threaded product in a form of metal-free active template synthesis. Rotaxane formation can proceed through the stabilization of different transition states featuring 5-coordinate (e.g., SN2) or 4-coordinate (e.g., acylation, Michael addition) carbon. Examples prepared using the approach include crown-ether-peptide rotaxanes and switchable molecular shuttles.

  我们报告了通过轴形成反应的过渡态稳定化合成冠醚-铵、酰胺和胺 [2] 轮烷。与轮烷合成中通常使用的两步“剪切”和“封盖”策略相反，这里的组分在动力学控制下以单一、无试剂的步骤组装成互锁分子。冠醚通过空腔加速形成轴的组分的反应，以无金属活性模板合成的形式提供螺纹产品。轮烷的形成可以通过以 5 配位（例如 SN2）或 4 配位（例如酰化、迈克尔加成）碳为特征的不同过渡态的稳定化进行。使用该方法制备的例子包括冠醚肽轮烷和可切换的分子穿梭。
• JANUS WEDGES: a new approach towards nucleobase-pair recognition
  作者：Neil Branda、Guido Kurz、Jean-Marie Lehn

  DOI：10.1039/cc9960002443

  日期：——

  The two-faced JANUS-type heterocycles 1a and 1b are designed to recognize a cytosine–uracil mismatched basepair by insertion in a wedge-like fashion between the bases to give a triad motif utilizing the maximum number of Watson–Crick interactions, as shown by 1H NMR spectroscopic studies.

  如 1H NMR 光谱研究所示，双面 JANUS 型杂环 1a 和 1b 设计用于识别胞嘧啶-尿嘧啶错配碱基对，以楔形方式插入碱基之间，从而利用最大数量的沃森-克里克（Watson-Crick）相互作用形成三元组图案。
• Thioamide-Substituted Cinchona Alkaloids as Efficient Organocatalysts for Asymmetric Decarboxylative Reactions of MAHOs
  作者：Yuttapong Singjunla、Morgane Pigeaux、Romain Laporte、Jérôme Baudoux、Jacques Rouden

  DOI：10.1002/ejoc.201700870

  日期：2017.8.10

  practical approach was developed to insert the thioamide functional group onto the cinchonidine from readily available dithioesters. These organocatalysts were effective in asymmetric decarboxylative Mannich and protonation reactions of alpha-amido-substituted Malonic Acid Half Oxyesters (MAHOs) affording alpha,beta- and alpha-amino acid derivatives in good yields and stereoselectivities respectively.

  报告了一类新的硫代酰胺取代的金鸡纳衍生物。开发了一种收敛且实用的方法，将硫代酰胺官能团从容易获得的二硫酯中插入到辛可尼丁上。这些有机催化剂在 α-酰氨基取代的丙二酸半氧酯 (MAHO) 的不对称脱羧曼尼希和质子化反应中是有效的，分别以良好的产率和立体选择性提供了 α、β-和α-氨基酸衍生物。

表征谱图