2-methylbenzyl tosylate | 41194-46-1

• 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: 2-methylbenzyl tosylate
• 英文别名: o-Methylbenzyl tosylate；(2-methylphenyl)methyl 4-methylbenzenesulfonate
• CAS: 41194-46-1
• 化学式: C₁₅H₁₆O₃S
• 分子量: 276.356
• InChiKey: MTIVQQJGYDPVAX-UHFFFAOYSA-N

物化性质

• 沸点：
  428.2±24.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  2-methylbenzyl tosylate 、 苯硼酸 在 NHC-Pd(II)-Im 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以94%的产率得到苄基甲苯
  参考文献：
  名称：

  N-heterocyclic carbene–palladium(ii)-1-methylimidazole complex-catalyzed Suzuki–Miyaura coupling of benzyl sulfonates with arylboronic acids

  摘要：

  第一个钯催化的苯甲基磺酸酯和芳基硼酸之间的偶联反应的例子被报道了。

  DOI：

  10.1039/c4ob02675f
• 作为产物：
  描述：

  邻甲基苄醇 、 对甲苯磺酰氯 在 sodium hydride 作用下， 生成 2-methylbenzyl tosylate
  参考文献：
  名称：

  抗体催化阳离子环化的方法：离去基团和环化模式的化学研究

  摘要：

  已经研究了2-甲基苄基醇10的一系列酯的溶剂化。发现磺酸酯在水溶液中溶解非常快（t 1/ 2≈35 s），而亚磺酸盐反应缓慢（t 1/ 2≈35 h），膦酸酯二酯是稳定的。荧光5-二甲基氨基萘-1-磺酸酯（丹宁酸酯）（例如22）作为抗体催化阳离子环化的底物最有希望。它是由显示18 O形标记研究该酯13主要是水解（但不排他地）被S Ñ在苄基位置1个反应。

  DOI：

  10.1002/ijch.199600022

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。
• [EN] PROCESS FOR PREPARING 2-EXO-(2-METHYLBENZYLOXY)-1-METHYL-4-ISOPROPYL-7-OXABICYCLO[2.2.1]HEPTANE<br/>[FR] PROCÉDÉ DE PRÉPARATION DE 2-EXO-(2-MÉTHYLBENZYLOXY)-1-MÉTHYL-4-ISOPROPYL-7-OXABICYCLO[2.2.1]HEPTANE
  申请人：BASF AGRO BV

  公开号：WO2018177907A1

  公开（公告）日：2018-10-04

  This invention relates to a process for preparing (±)-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane of the formula (I) (I), any of its individual enantiomers or any non-racemic mixture thereof, comprising the step of reacting (±)-2-exo-hydroxy-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane of the formula (II) (II), any of its individual enantiomers or any non-racemic mixture thereof with a 2-Methylbenzyl compound of the formula (III) (III), wherein X is a leaving group, in the presence of at least one base, at least one catalyst selected from rubidium salts, cesium salts and any combination thereof and at least one inert organic solvent S1.

  该发明涉及一种制备(±)-2-外消旋-(2-甲基苄氧基)-1-甲基-4-异丙基-7-氧杂双环[2.2.1]庚烷的过程，其化学式为(I)，任何其个别对映体或其非外消旋混合物，包括以下步骤：将(±)-2-外消旋-羟基-1-甲基-4-异丙基-7-氧杂双环[2.2.1]庚烷的化学式为(II)，任何其个别对映体或其非外消旋混合物与化学式(III)的2-甲基苄基化合物反应，其中X是一个脱离基，在至少一种碱、至少一种选择自铷盐、铯盐和二者任意组合的催化剂和至少一种惰性有机溶剂S1的存在下。
• [EN] PROCESS FOR PREPARING 2-EXO-(2-METHYLBENZYLOXY)-1-METHYL-4-ISOPROPYL-7-OXABICYCLO[2.2.1]HEPTANE<br/>[FR] PROCÉDÉ DE PRÉPARATION DE 2-EXO- (2-MÉTHYLBENZYLOXY)-1-MÉTHYL-4-ISOPROPYL-7-OXABICYCLO [2.2.1] HEPTANE
  申请人：BASF AGRO BV

  公开号：WO2018050518A1

  公开（公告）日：2018-03-22

  This invention relates to a process for preparing (±)-2-exo-(2-Methylbenzyloxy)-1-methyl-4-iso- propyl-7-oxabicyclo[2.2.1]heptane of the formula (I), any of its individual enantiomers or any non-racemic mixture thereof, comprising the steps of (a) reacting (±)-2-exo-hydroxy-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptaneof the formula (II), any of its individual enantiomers or any non-racemic mixture thereof with a 2-Methylbenzyl compound of the formula (III) wherein X is a leaving group in the presence of at least one base capable of forming water or a C1 -C 4 alkyl alcohol under the reaction conditions, and at least one inert organic sol- vent, and (b) simultaneously removing water, the C1-C4 alkyl alcoholor any mixture thereof from the reaction mixture.

  这项发明涉及制备(±)-2-外消旋-(2-甲基苄氧基)-1-甲基-4-异丙基-7-氧代-2-环丙基[2.2.1]庚烷的方法，其化学式为(I)，包括以下步骤：(a)将(±)-2-外消旋-羟基-1-甲基-4-异丙基-7-氧代-2-环丙基[2.2.1]庚烷的化学式(II)，其任一手性体或非旋光混合物与化学式(III)中X为脱离基的2-甲基苄化合物在至少一种能够在反应条件下生成水或C1-C4烷基醇的碱存在下反应，并在至少一种惰性有机溶剂中进行；(b)同时从反应混合物中移除水、C1-C4烷基醇或二者的混合物。
• Catalyst and process for preparing low-viscosity and color-reduced polyisocyanates containing isocyanurate groups
  申请人：DEGUSSA AG

  公开号：US20030187178A1

  公开（公告）日：2003-10-02

  A low-viscosity polyisocyanates and polyisocyanates of reduced color containing isocyanurate groups is prepared by a process comprising, partially trimerizing aliphatic and/or cycloaliphatic diisocyanates in the presence of 0.02 to 2% by weight, based on the weight of the diisocyanate starting material, of at least one trimerization catalyst of formula (I) 1 wherein and wherein substituents A, B, C, D, and E simultaneously or independently of one another are hydrogen, chloro, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxycarbonyl, hydroxyl, (R 5 ) 3 SiO—, (R 5 ) 2 N—, —COOH, (R 5 ) 2 N—CH 2 — or phenyl, it being 5 possible for any two adjacent radicals selected from the group A, B, C, D and E to form a conjoint 5- or 6-membered saturated or unsaturated ring which may also include nitrogen, sulfur or oxygen heteroatoms; F is hydrogen, methyl or fluoro; G is hydrogen, methyl or fluoro; R 2 and R 3 simultaneously or independently of one another are C 1 -C 18 -alkyl or R 1 ; R 4 is hydrogen, methyl, C 2 -C 18 -alkyl, C 3 -C 8 -cycloalkyl or C 2 -C 12 -alkoxy; R 5 is C 1 -C 18 -alkyl; Y − is R 6 COO − ; R 6 is hydrogen or a branched or unbranched aliphatic or araliphatic C 1 -C 12 -alkyl radical, and then removing excess diisocyanate from the reaction medium.

  通过部分三聚脂肪族和/或环脂肪族二异氰酸酯在至少一种式(I)的三聚催化剂的存在下进行部分三聚化反应，其中所述催化剂的重量为二异氰酸酯起始物的重量的0.02至2％。所述催化剂的式子如下：其中，取代基A、B、C、D和E可以同时或独立地是氢、氯、C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷氧羰基、羟基、(R5)3SiO-、(R5)2N-、-COOH、(R5)2N-CH2-或苯基，其中任意相邻的两个基团A、B、C、D和E中选择的基团可以形成共轭的5-或6-成员饱和或不饱和环，该环还可以包括氮、硫或氧杂原子；F为氢、甲基或氟；G为氢、甲基或氟；R2和R3可以同时或独立地是C1-C18烷基或R1；R4为氢、甲基、C2-C18烷基、C3-C8环烷基或C2-C12烷氧基；R5为C1-C18烷基；Y-为R6COO-；R6为氢或支链或非支链的脂肪族或芳基脂肪族C1-C12烷基基团，然后从反应介质中去除多余的二异氰酸酯，从而制备含有异氰酸酯基团的低粘度聚异氰酸酯和降低颜色的聚异氰酸酯。
• Process for preparing 2-exo-(2-methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane
  申请人：BASF Agro B.V.

  公开号：US10710969B2

  公开（公告）日：2020-07-14

  This invention relates to a process for preparing (±)-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane of the formula (I) any of its individual enantiomers or any non-racemic mixture thereof, comprising the steps of (a) reacting (±)-2-exo-hydroxy-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane of the formula (II) any of its individual enantiomers or any non-racemic mixture thereof with a 2-Methylbenzyl compound of the formula (III) wherein X is a leaving group in the presence of at least one base capable of forming water or a C1-C4 alkyl alcohol under the reaction conditions, and at least one inert organic solvent, and (b) simultaneously removing water, the C1-C4 alkyl alcohol or any mixture thereof from the reaction mixture.

  本发明涉及一种制备(±)-2-外-(2-甲基苄氧基)-1-甲基-4-异丙基-7-氧杂双环[2.2.1]庚烷的工艺，其式为(I) 其任何单个对映体或任何非外消旋混合物，包括以下步骤 (a) 使式 (II) 的(±)-2-外-羟基-1-甲基-4-异丙基-7-氧杂双环[2.2.1]庚烷反应 其任何单个对映体或其任何非外消旋混合物与式 (III) 的 2-甲基苄基化合物的混合物 其中 X 是离去基团，在至少一种在反应条件下能形成水或 C1-C4 烷醇的碱和至少一种惰性有机溶剂存在下，以及 (b) 同时从反应混合物中除去水、C1-C4 烷醇或它们的混合物。