toluene-4-sulfonic acid [3-(4-chlorophenyl)-2-propyn-1-yl] ester | 273730-30-6

• 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: toluene-4-sulfonic acid [3-(4-chlorophenyl)-2-propyn-1-yl] ester
• 英文别名: 3-(4-chlorophenyl)prop-2-yn-1-yl 4-methylbenzenesulfonate；toluene-4-sulfonic acid 3-(4-chloro-phenyl)-prop-2-ynyl ester；3-(4-chlorophenyl)prop-2-ynyl 4-methylbenzenesulfonate
• CAS: 273730-30-6
• 化学式: C₁₆H₁₃ClO₃S
• 分子量: 320.796
• InChiKey: RWYCRODLMZDPMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  toluene-4-sulfonic acid [3-(4-chlorophenyl)-2-propyn-1-yl] ester 、 生成
  参考文献：
  名称：

  Alpha-sulfin-and alpha-sulfonamino acid amide derivatives

  摘要：

  本发明涉及一种新的具有杀虫活性的α-亚砜和α-磺酰氨基酸酰胺，其通式为(I)，包括其光学异构体和混合物，其中n为零或一；R1、R2、R3、R4、R5、R6和R7具有规范中给出的含义，R8为氢、(a)、(b)、(c)、(d)或(e)，其中R11、R12、R13、R15和R17各自独立地为氢或C1-C4烷基，R13为C4-C12烷基，C1-C12卤代烷基；C3-C8环烷基；可选取代芳基或可选取代杂环芳基，R16为可选取代芳基或可选取代杂环芳基；Z为氧、硫- CR18R19-或-NR2O-，其中R18、R19和R20各自独立地为氢或C1-C4烷基。这些新化合物具有保护植物的性质，适用于保护植物免受植物病原微生物的侵害。

  公开号：

  US20030224940A1
• 作为产物：
  描述：

  对氯碘苯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 16.0h， 生成 toluene-4-sulfonic acid [3-(4-chlorophenyl)-2-propyn-1-yl] ester
  参考文献：
  名称：

  Removal of Human Ether-à-go-go Related Gene (hERG) K⁺ Channel Affinity through Rigidity: A Case of Clofilium Analogues

  摘要：

  Cardiotoxicity is a side effect that plagues modern drug design and is very often due to the off-target blockade of the human ether-a-go-go related gene (hERG) potassium channel. To better understand the structural determinants of this blockade, we designed and synthesized a series of 40 derivatives of clofilium, a class III antiarrhythrnic agent. These were evaluated in radioligand binding and patch-damp assays to establish structure affinity relationships (SAR) for this potassium channel. Efforts were especially focused on studying the influence of the structural rigidity and the nature of the linkers composing the clofilium scaffold. It was shown that introducing triple bonds and oxygen atoms in the n-butyl linker of the molecule greatly reduced affinity without significantly modifying the pK(a) of the essential basic nitrogen. These findings could prove useful in the first stages of drug discovery as a systematic way of reducing the risk of hERG K+ channel blockade-induced cardiotoxicity.

  DOI：

  10.1021/jm4010434

文献信息

• alpha-sulfin-and alpha-sulfonamino acid amides
  申请人：——

  公开号：US20020082452A1

  公开（公告）日：2002-06-27

  The invention relates to &agr;-sulfin- and &agr;-sulfonamino acid amides of the general formula I 1 including the optical isomers thereof and mixtures of such isomers, wherein n is a number zero or one; R 1 is C 1 -C 12 alkyl, C 1 -C 12 alkyl substituted with C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfonyl, C 3 -C 8 cycloalkyl, cyano, C 1 -C 6 alkoxycarbonyl, C 3 -C 6 alkenyloxycarbonyl or C 3 -C 6 alkynyloxycarbonyl; C 3 -C 8 cycloalkyl; C 2 -C 12 alkenyl; C 2 -C 12 alkynyl; C 1 -C 12 haloalkyl; or a group NR 12 R 13 wherein R 12 and R 13 are each independently of the other hydrogen or C 1 -C 6 -alkyl, or together are tetra- or penta-methylene; R 2 and R 3 are each independently hydrogen; C 1 -C 8 alkyl; C 1 -C 8 alkyl substituted with hydroxy, mercapto, C 1 -C 4 alkoxy or C 1 -C 4 alkylthio; C 3 -C 8 alkenyl; C 3 -C 8 alkynyl; C 3 -C 8 cycloalkyl; C 3 -C 8 cycloalkyl-C 1 -C 4 alkyl; or the two groups R 2 and R 3 together with the carbon atom to which they are bonded form a three- to eight-membered hydrocarbon ring; R 4 , R 5 , R 6 and R 7 are each independently hydrogen or C 1 -C 4 alkyl; R 8 is C 1 -C 6 alkyl, C 3 -C 6 alkenyl or C 3 -C 6 alkynyl; R 9 and R 10 are each independently hydrogen or C 1 -C 4 alkyl; and R 11 is either 2 R 14 , R 15 , R 16 and R 17 are each independently hydrogen or C 1 -C 4 alkyl, X is oxygen, sulfur or —NR 18 —, wherein R 18 is hydrogen or C 1 -C 4 alkyl, and A is optionally substituted mono- or polycylic aryl or heteroaryl, and to the preparation of those substances and to agrochemical compositions comprising at least one of those compounds as active ingredient. The invention relates also to the preparation of compositions and to the use of the compounds or of the compositions in controlling or preventing the infestation of plants by phytopathogenic microorganisms, especially fungi.

  该发明涉及一般式I的α-亚砜和α-磺酰氨基酸酰胺，包括其光学异构体和这些异构体的混合物，其中n是零或一的数字；R1是C1-C12烷基，C1-C12烷基取代C1-C4烷氧基，C1-C4烷基硫醚基，C1-C4烷基磺酰基，C3-C8环烷基，氰基，C1-C6烷氧羰基，C3-C6烯氧羰基或C3-C6炔氧羰基；C3-C8环烷基；C2-C12烯基；C2-C12炔基；C1-C12卤代烷基；或一个NR12R13基团，其中R12和R13各自独立地是氢或C1-C6烷基，或者一起是四甲基或五甲基；R2和R3各自独立地是氢；C1-C8烷基；C1-C8烷基取代羟基，巯基，C1-C4烷氧基或C1-C4烷基硫基；C3-C8烯基；C3-C8炔基；C3-C8环烷基；C3-C8环烷基-C1-C4烷基；或两个基团R2和R3与它们结合的碳原子一起形成三至八元环烃环；R4、R5、R6和R7各自独立地是氢或C1-C4烷基；R8是C1-C6烷基，C3-C6烯基或C3-C6炔基；R9和R10各自独立地是氢或C1-C4烷基；R11是2R14，R15，R16和R17各自独立地是氢或C1-C4烷基，X是氧、硫或-NR18-，其中R18是氢或C1-C4烷基，A是可选取代的单环或多环芳基或杂环芳基，以及制备这些物质和包含至少一种这些化合物作为活性成分的农药组合物。该发明还涉及组合物的制备以及化合物或组合物在控制或预防植物受植物病原微生物，特别是真菌，侵害方面的用途。
• Lead-Discovery of bis-Aromatic Alkynes: A Novel Class of Herbicides
  作者：Jutta Glock、Peter D. J. Grootenhuis、Steven Bondy、Daniel D. Comer、Soan Cheng、Arthur Steiger、Martin Zeller、Grit Laue、Adrian Friedmann、Olivier Jacob、Mafalda Nina、Hans-Jürg Widmer、Klaus Kreuz、Julie E. Penzotti、Hans Brunner、James Allen、Thierry Niderman、Hans Ulrich Haas、Renold Chollet、Martin Eberle、Peter Renold、William Lutz、Jürg Ehrler、Marian Valentini、Markus Walti、Evelyne Sieger、Thomas Vettiger、G. Wayne Craig

  DOI：10.2533/chimia.2008.23

  日期：——

  The search for new active molecules with novel modes of action and desirable physical properties is an ongoing endeavour. This publication describes the follow-up chemistry of a biological hit discovered in the screening system of Novartis Crop Protection, the legacy agrochemical parent of Syngenta Crop Protection. This chemistry was optimized through classical synthetic methods and automated parallel synthesis with coverage of important physical properties such as lipophilicity or Clog P and solubility. Preliminary biological activity from the greenhouse and field data with symptomology is presented.

  寻找具有新颖作用方式和理想物理特性的新活性分子是一项持续进行的努力。本出版物描述了在先正达作物保护的筛选系统中发现的生物活性物质的后续化学研究，该系统是辛吉塔作物保护的传统农药母公司。通过经典合成方法和自动并行合成对这种化学物质进行了优化，涵盖了重要的物理特性，如亲脂性或Clog P和溶解度。介绍了来自温室和田间数据的初步生物活性和症状学。
• Propargylether derivatives
  申请人：Syngenta Participations AG

  公开号：US06469005B1

  公开（公告）日：2002-10-22

  Propargylether derivatives of formula I including the optical isomers thereof and mixtures of such isomers, wherein R1 is hydrogen, alkyl, cycloalkyl or optionally substituted aryl, R2 and R3 are each independently hydrogen or alkyl, R4 is alkyl, alkenyl or alkynyl, R5, R6, R7, and R8 are each independently hydrogen or alkyl and R9 is a group R10 is optionally substituted aryl or optionally substituted heteroaryl, R11 is hydrogen or optionally substituted alkyl, alkenyl or alkynyl, Z is hydrogen —CO—R16, —COOR16, —CO—COOR16 or —CONR16R17, R12 is hydrogen, or optionally substituted alkyl, alkenyl or alkynyl, R13 is hydrogen or alkyl, R14 is hydrogen, alkyl, cycloalkyl or cycloalkyl-alkyl, R15 is alkyl, alkenyl, alkynyl, optionally substituted aryl or optionally substituted aryl-alkyl, and R16 and R17 are independently of each other hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl or optionally substituted heteroaryl, have been found to be useful for controlling or preventing the infestation of plants by phytopathogenic microorganisms, especially fungi. The invention relates the novel compounds and also to the preparation thereof and to the use of the compounds for plant protection, and to compositions suitable for applying the novel compounds in agricultural techniques.

  式I的Propargylether衍生物包括其光学异构体和这些异构体的混合物，其中R1是氢，烷基，环烷基或可选择取代的芳基，R2和R3分别独立地是氢或烷基，R4是烷基，烯基或炔基，R5、R6、R7和R8分别独立地是氢或烷基，R9是基团，R10是可选择取代的芳基或可选择取代的杂环芳基，R11是氢或可选择取代的烷基，烯基或炔基，Z是氢，-CO-R16，-COOR16，-CO-COOR16或-CONR16R17，R12是氢或可选择取代的烷基，烯基或炔基，R13是氢或烷基，R14是氢，烷基，环烷基或环烷基-烷基，R15是烷基，烯基，炔基，可选择取代的芳基或可选择取代的芳基-烷基，R16和R17独立地是氢，可选择取代的烷基，可选择取代的环烷基，可选择取代的芳基或可选择取代的杂环芳基，已被发现对控制或预防植物受植物病原微生物，尤其是真菌的侵害具有有用性。该发明涉及新颖的化合物，以及其制备和用于植物保护的化合物的用途，以及适用于在农业技术中应用新化合物的组合物。
• Halohydroxylation of 1-Cyclopropylallenes: An Efficient and Stereoselective Method for the Preparation of Multisubstituted Olefins
  作者：Lei Yu、Bo Meng、Xian Huang

  DOI：10.1021/jo801087d

  日期：2008.9.1

  The halohydroxylation of 1-cyclopropylallenes would generate two multisubstituted C=C double bonds and at the same time stereoselectively gives 5-halohexa-3,5-dien-1-ols in moderate to good yields. The latter could be transformed into the corresponding alkynyl-substituted conjugated dienes through the further Sonogashira coupling.

  1-环丙基丙烯的卤代羟基化反应将产生两个多取代的C = C双键，同时立体选择性地以中等至良好的收率生成5-卤代六-3,5-二烯-1-醇。后者可以通过进一步的Sonogashira偶联转化为相应的炔基取代的共轭二烯。
• Microbicidal N-sulfonylglycin alkynyloxyphenethyl amide derivatives
  申请人：Syngenta Crop Protection, Inc.

  公开号：US06482859B1

  公开（公告）日：2002-11-19

  The invention relates to novel pesticidally active compounds of the general formula I as well as possible isomers and mixtures of isomers thereof, wherein n is a number zero or one; and R1 is C1-C12alkyl that is unsubstituted or may be substituted by C1-C4alkoxy, C1-C4alkylthio, C1-C4alkylsulfonyl, C3-C8cycloalkyl, cyano, C1C6alkoxycarbonyl, C3-C6alkenyloxycarbonyl or by C3-C6alkynyloxycarbonyl; C3-C8cycloalkyl; C2-C12alkenyl; C2-C12alkynyl; C1-C12haloalkyl: or a group NR11R12 wherein R11 and R12 are each independently of the other hydrogen or C1-C8alkyl, or together are tetra- or penta-methylene; R2 and R3 are each independently of the other hydrogen; C1-C8alkyl; C1-C8alkyl substituted by hydroxy, C1-C4alkoxy, mercapto or by C1-C4alkylthio; C3-C8alkenyl; C3-C8alkynyl; C3-C8cycloalkyl; C3-C8cycloalkyl-C1-C4alkyl; or the two groups R2 and R3 together with the carbon atom to which they are bonded form a three- to eight-membered ring; R4, R5, R6 and R7 are identical or different and are each independently of the others hydrogen or C1-C4alkyl; R8 is C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl; A is C1-C6alkylene; and B is optionally mono- or poly-nuclear, unsubstituted or substituted aryl; optionally mono- or poly-nuclear, unsubstituted or substituted heteroaryl; C4-C12alkyl; or C3-C8cycloalkyl. The novel compounds have plant-protecting properties and are suitable for protecting plants against infestation by phytopathogenic microorganisms.

  本发明涉及一般式I的新型杀虫活性化合物，以及其可能的异构体和异构体混合物，其中n是0或1；R1是C1-C12烷基，未取代或可被C1-C4烷氧基，C1-C4烷基硫醚，C1-C4烷基磺酰基，C3-C8环烷基，氰基，C1C6烷氧羰基，C3-C6烯氧羰基或C3-C6炔氧羰基取代；C3-C8环烷基；C2-C12烯基；C2-C12炔基；C1-C12卤代烷基；或一个NR11R12基团，其中R11和R12各自独立地是氢或C1-C8烷基，或者一起是四亚甲基或五亚甲基；R2和R3各自独立地是氢；C1-C8烷基；C1-C8烷基，被羟基，C1-C4烷氧基，巯基或C1-C4烷基硫醚取代；C3-C8烯基；C3-C8炔基；C3-C8环烷基；C3-C8环烷基-C1-C4烷基；或两个R2和R3基团与它们连接的碳原子一起形成三至八元环；R4、R5、R6和R7相同或不同，各自独立地是氢或C1-C4烷基；R8是C1-C6烷基，C3-C6烯基或C3-C6炔基；A是C1-C6烷基；B是可选的单核或多核，未取代或取代的芳基；可选的单核或多核，未取代或取代的杂环芳基；C4-C12烷基；或C3-C8环烷基。这些新化合物具有植物保护性能，适用于保护植物免受植物病原微生物侵害。