3-chlorobenzyl tosylate | 14503-42-5

• 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-chlorobenzyl tosylate
• 英文别名: m-chlorobenzyl tosylate；toluene-4-sulfonic acid-(3-chloro-benzyl ester)；Toluol-4-sulfonsaeure-(3-chlor-benzylester)；(3-Chlorophenyl)methyl 4-methylbenzene-1-sulfonate；(3-chlorophenyl)methyl 4-methylbenzenesulfonate
• CAS: 14503-42-5
• 化学式: C₁₄H₁₃ClO₃S
• 分子量: 296.774
• InChiKey: BLBANPDKCIHJJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 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-chlorobenzyl tosylate 、 氰化四乙基铵 在 4-硝基甲苯 作用下， 以 水 、 乙腈 为溶剂， 生成 间氯氰苄
  参考文献：
  名称：

  Using ¹¹C/¹⁴C Incoming Group and Secondary α-Deuterium KIEs To Determine How a Change in Leaving Group Alters the Structure of the Transition State of the S_N2 Reactions between m-Chlorobenzyl para-Substituted Benzenesulfonates and Cyanide Ion

  摘要：

  The C-11/C-14 incoming group and secondary alpha-deuterium KIEs and Hammett rho value found by changing the substituent in the leaving group of the S(N)2 reactions between meta-chlorobenzyl para-substituted benzenesulfonates and cyanide ion in 0.5% aqueous acetonitrile at 0 degrees C suggest that these reactions occur via an unsymmetrical, product-like transition state. Changing to a better leaving group leads to a transition state with a slightly shorter nucleophile-alpha-carbon bond and a longer alpha-carbon-leaving group bond. The changes in transition state structure are consistent with the Bond Strength Hypothesis.

  DOI：

  10.1021/ja972981u
• 作为产物：
  描述：

  3-氯苯甲醇 、 对甲苯磺酰氯 在 sodium hydride 作用下， 以 乙醚 为溶剂， 以16%的产率得到3-chlorobenzyl tosylate
  参考文献：
  名称：

  Gordon, Isobel M.; Maskill, H., Journal of the Chemical Society. Perkin transactions II, 1991, # 12, p. 1951 - 1954

  摘要：

  DOI：

文献信息

• Anilides related to substituted benzamides. Potential antipsychotic activity of N-(4-amino-5-chloro-2-methoxyphenyl)-1-(phenylmethyl)-4-piperidinecarboxamide
  作者：Frank E. Blaney、Michael S. G. Clark、Derek V. Gardner、Michael S. Hadley、David Middleton、Trevor J. White

  DOI：10.1021/jm00366a017

  日期：1983.12

  The substituted benzamides are used clinically both as antipsychotics and as stimulants of gastric motility. The antipsychotic effects are considered to be a consequence of their central dopamine antagonist properties, but there is evidence that the gastric stimulatory effects may be mediated by other mechanisms. Clebopride (3) is a substituted benzamide that although marketed for its stimulatory effects

  取代的苯甲酰胺在临床上既用作抗精神病药，又用作胃动力的兴奋剂。抗精神病作用被认为是其中央多巴胺拮抗剂特性的结果，但是有证据表明，胃刺激作用可能是由其他机制介导的。Clebopride（3）是一种取代的苯甲酰胺，尽管因其对胃蠕动的刺激作用而上市，但它也是有效的中枢多巴胺拮抗剂。已合成了酰胺键已被逆转的相应的苯胺化物BRL 20596（4a），发现其缺乏胃刺激活性。但是，有效的中枢多巴胺拮抗剂活性得以保留，表明苯甲酰胺和苯胺对中枢多巴胺受体具有相似的亲和力。讨论了在这些受体上苯甲酰胺和苯甲酰胺采用的构象的含义。也有证据表明，在这类受体上还有一个亲脂性结合位点，N-苄基最适合。
• Alpha-sulfin-and alpha-sulfonamino acid amide derivatives
  申请人：——

  公开号：US20030224940A1

  公开（公告）日：2003-12-04

  The invention relates to novel pesticidally active &agr;-sulfin and &agr;-sulfonamino acid amides of the general formula (I) including the optical isomers thereof and mixtures of such isomers, wherein n is a number zero or one; R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 have the meanings given in the specification, and R 8 is either hydrogen, (a), (b), (c), (d) or (e) wherein R 11 , R 12 , R 13 , R 15 and R 17 are each independently hydrogen or C 1 -C 4 alkyl, R 13 is C 4 -C 12 alkyl, C 1 -C 12 halogenalkyl; C 3 -C 8 cycloalkyl; optionally substituted aryl or optionally substituted heteroaryl, R 16 is optionally substituted aryl or optionally substituted heteroaryl; and Z is oxygen, sulfur —CR 18 R 19 — or —NR 2O —, wherein R 18 , R 19 and R 20 independently of each other are hydrogen or C 1 -C 4 alkyl. The novel compounds possess plant-protecting properties and are suitable for protecting plants against infestation by phytopathogenic microorganisms.

  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。
• Condensed pyrazole derivatives, method of manufacturing the same, and androgen inhibitor
  申请人：OTSUKA PHARMACEUTICAL CO., LTD.

  公开号：EP0594149A2

  公开（公告）日：1994-04-27

  This invention provides a condensed pyrazole derivative of the Formula (1) : (where A denotes CH or N, RO and R3 denote same or different, a hydrogen atom or a lower alkyl group, R1 and R2 denote same or different, a hydrogen atom, a lower alkyl group, a lower alkoxy group, a lower alkylthio group, a nitro group or a halogen atom, m denotes 1 or 2, and n denotes 1, 2 or 3, provided that, when n is 2, two R2 may be connected to each other to form a lower alkylenedioxy group), or its pharmaceutically acceptable salt. This derivative or its salt is excellent in the effect of inhibiting the expression of action of androgen, thereby being excellent in therapeutical effect of benign prostatic hypertrophy, prostatic carcinoma, etc., and has a long lasting of efficacy and high oral absorption.

  本发明提供了一种式（1）的缩合吡唑衍生物： (其中A表示CH或N，RO和R3表示相同或不同的氢原子或低级烷基，R1和R2表示相同或不同的氢原子、低级烷基、低级烷氧基、低级烷硫基、硝基或卤素原子，m表示1或2，n表示1、2或3，但当n为2时，两个R2可相互连接形成低级烷二氧基)，或其药学上可接受的盐。该衍生物或其盐具有良好的抑制雄激素作用表达的效果，从而对良性前列腺肥大、前列腺癌等具有良好的治疗效果，且药效持久，口服吸收率高。
• Acetolysis reactivities of substituted benzyl and polycyclic arylmethyl p-toluenesulfonates. Correlations with SCF [self-consistant field]-.pi. and CNDO [complete neglect of differential overlap] MO methods
  作者：Andrew Streitwieser、H. A. Hammond、R. H. Jagow、Richard Murray Williams、R. G. Jesaitis、C. J. Chang、Robert Wolf

  DOI：10.1021/ja00720a025

  日期：1970.8
• Discovery and Characterization of (<i>R</i>)-6-Neopentyl-2-(pyridin-2-ylmethoxy)-6,7-dihydropyrimido[2,1-<i>c</i>][1,4]oxazin-4(9<i>H</i>)-one (PF-06462894), an Alkyne-Lacking Metabotropic Glutamate Receptor 5 Negative Allosteric Modulator Profiled in both Rat and Nonhuman Primates
  作者：Antonia F. Stepan、Michelle M. Claffey、Matthew R. Reese、Gayatri Balan、Gabriela Barreiro、Jason Barricklow、Michael J. Bohanon、Brian P. Boscoe、Gregg D. Cappon、Lois K. Chenard、Julie Cianfrogna、Laigao Chen、Karen J. Coffman、Susan E. Drozda、Joshua R. Dunetz、Somraj Ghosh、Xinjun Hou、Christopher Houle、Kapil Karki、John T. Lazzaro、Jessica Y. Mancuso、John M. Marcek、Emily L. Miller、Mark A. Moen、Steven O’Neil、Isao Sakurada、Marc Skaddan、Vinod Parikh、Deborah L. Smith、Patrick Trapa、Jamison B. Tuttle、Patrick R. Verhoest、Daniel P. Walker、Annie Won、Ann S. Wright、Jessica Whritenour、Kenneth Zasadny、Margaret M. Zaleska、Lei Zhang、Christopher L. Shaffer

  DOI：10.1021/acs.jmedchem.7b00604

  日期：2017.9.28

  We previously observed a cutaneous type IV immune response in nonhuman primates (NHP) with the mGlu(5) negative allosteric modulator (NAM) 7. To determine if this adverse event was chemotype- or mechanism-based, we evaluated a distinct series of mGlu(5) NAMs. Increasing the sp(3) character of high-throughput screening hit 40 afforded a novel morpholinopyrimidone mGlu(5) NAM series. Its prototype, (R)-6-neopentyl-2-(pyridin-2-ylmethoxy)-6,7-dihydropyrimido[2,1-c] [1,4]oxazin-4(9H)-one (PF-06462894, 8), possessed favorable properties and a predicted low clinical dose (2 mg twice daily). Compound 8 did not show any evidence of immune activation in a mouse drug allergy model. Additionally, plasma samples from toxicology studies confirmed that 8 did not form any reactive metabolites. However, 8 caused the identical microscopic skin lesions in NHPs found with 7, albeit with lower severity. Holistically, this work supports the hypothesis that this unique toxicity may be mechanism-based although additional work is required to confirm this and determine clinical relevance.