4-(hydroxymethyl)phenyl trifluoromethanesulfonate

• 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: 4-(hydroxymethyl)phenyl trifluoromethanesulfonate
• 英文别名: Trifluoromethanesulfonic acid 4-(hydroxymethyl)phenyl ester；[4-(hydroxymethyl)phenyl] trifluoromethanesulfonate
• 化学式: C₈H₇F₃O₄S
• 分子量: 256.202
• InChiKey: XQWNETQYODEXLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  72
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-(hydroxymethyl)phenyl trifluoromethanesulfonate 在 重铬酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以83%的产率得到4-(trifluormethanesulfonyloxy)benzaldehyde
  参考文献：
  名称：

  A polystyrene-supported triflating reagent for the synthesis of aryl triflates

  摘要：

  An insoluble polystyrene-supported triflating reagent has been prepared by suspension co-polymerization of N-(4-vinylphenyl)trifluoromethanesulphonimide, styrene and the JandaJel((R)) cross-linker. This reagent, in the presence of triethylamine, allows for the efficient synthesis of aryl triflates from a wide range of phenols in a process that permits the desired product to be isolated from the reaction mixture in essentially pure form via several filtration and concentration operations. Adding to the utility of this reagent is its ability to be easily recovered, regenerated and reused. Both soluble and insoluble bifunctional polymers containing trialkylamine moieties in addition to triflimide groups were also prepared and examined as triflating reagents. Unfortunately these reagents afforded only modest yields of the desired products in representative reactions. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.10.108
• 作为产物：
  描述：

  4-(trifluormethanesulfonyloxy)benzaldehyde 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 以353 mg的产率得到4-(hydroxymethyl)phenyl trifluoromethanesulfonate
  参考文献：
  名称：

  SNAP-25 针对肉毒杆菌神经毒素/A 的细胞保护：通过自杀底物机制抑制硫氧还蛋白还原酶

  摘要：

  肉毒杆菌神经毒素（BoNT）是人类已知的最致命的毒素之一。它们由七种血清型组成，其中 BoNT/A 是最致命的；然而，目前尚无批准的治疗药物中毒的方法，甚至还没有进入临床试验的治疗方法。肉毒杆菌的神经毒性最终是通过轻链 (LC) 蛋白酶 SNARE 蛋白裂解导致神经递质释放丧失来控制的。消除 BoNT/A 中毒的药理学尝试试图消除细胞毒素的进入或消除其复杂作用机制中发现的关键生化连接。在这方面，已有非肽类小分子抑制剂的报道浮出水面，但很少有报道显示出中和细胞毒性的功效，这是启动啮齿动物致死性研究之前的一个关键先决条件。基于我们在 BoNT/A 细胞检测活动中发现的先导化合物，我们研究了基于结构活性关系 (SAR) 基础的 N-羟基琥珀酰亚胺抑制剂家族。理论上，源自该 SAR 活动的分子是蛋白酶抑制剂。然而，这一主张在广泛的动力学分析的基础上被推翻了。出乎意料的是，抑制剂数据指向硫氧还蛋白还原酶

  DOI：

  10.1021/jacs.5b12929

文献信息

• Selective Arylation and Vinylation at the α Position of Vinylarenes
  作者：Yinjun Zou、Liena Qin、Xinfeng Ren、Yunpeng Lu、Yongxin Li、Jianrong (Steve) Zhou

  DOI：10.1002/chem.201203646

  日期：2013.3.4

  styrene and vinylarenes, the aryl and vinyl groups routinely insert at the β position. However, selective insertion at the α position has been very rare. Herein, we provide a missing piece in the palette of Heck reaction, which gave >20:1 α selectivity. The key to our success is a new ferrocene 1,1′‐bisphosphane (dnpf) that carries 1‐naphthyl groups. Our mechanistic studies revealed that the high α selectivity

  在苯乙烯和乙烯基芳烃的分子间Heck反应中，芳基和乙烯基通常插入β位置。然而，在α位置的选择性插入非常罕见。在这里，我们在Heck反应的调色板中提供了一个缺失的片段，该片段给出了> 20：1的α选择性。我们成功的关键是带有1-萘基的新型二茂铁1,1'-双膦（dnpf）。我们的机理研究表明，较高的α选择性部分归因于dnpf的空间效应。dnpf的刚性和庞大的1-萘基在空间上不利于β插入。
• Achieving Vinylic Selectivity in Mizoroki-Heck Reaction of Cyclic Olefins
  作者：Xiaojin Wu、Yunpeng Lu、Hajime Hirao、Jianrong Steve Zhou

  DOI：10.1002/chem.201204427

  日期：2013.5.3

  In Heck reactions of cyclic olefins, the products usually have aryl groups that end up at the allylic and/or homoallylic position. We herein report new selectivity that adds aryl groups to the vinylic position. Cyclic olefins of various ring size worked well. The desired isomers were produced by palladium–hydride‐catalyzed isomerization of the initial products. Thus, a specific catalyst must be used

  在环烯烃的Heck反应中，产物通常具有芳基，该芳基最终在烯丙基和/或均烯丙基位置。我们在本文中报道了新的选择性，该选择性将芳基添加到乙烯基位置。各种环大小的环烯烃均能很好地发挥作用。所需的异构体是通过氢化钯催化的初始产物异构化反应制得的。因此，必须使用特定的催化剂，以使其可以在一组反应条件下进行两项工作。
• TRIAZINONE COMPOUND AND T-TYPE CALCIUM CHANNEL INHIBITOR
  申请人：NISSAN CHEMICAL INDUSTRIES, LTD.

  公开号：US20150065705A1

  公开（公告）日：2015-03-05

  There is provided a novel triazinone compound that has an excellent T-type voltage-dependent calcium channel inhibitory activity and is specifically useful for treatment of pain. A compound of Formula (I), a tautomer of the compound, a pharmaceutically acceptable salt thereof, or a solvate thereof: where each substituent is defined in detail in the description or claims, for example R 1 is H or C 1-6 alkoxy, etc., each of L 1 and L 2 is independently a single bond or NR 2 , etc., L 3 is C 1-6 alkylene, etc., A is C 6-14 aryl or 5 to 10-membered heteroaryl which is optionally substituted, etc., B is C 3-11 cycloalkylene, etc., D is C 6-14 aryl or 5 to 10-membered heteroaryl which is optionally substituted, etc.

  提供了一种新型三嗪酮化合物，具有出色的T型电压依赖性钙离子通道抑制活性，并且特别适用于治疗疼痛。化合物式(I)的化合物，其互变异构体，其药学上可接受的盐或其溶剂化物：其中每个取代基在说明或权利要求书中详细定义，例如R1为H或C1-6烷氧基等，每个L1和L2分别独立地为单键或NR2等，L3为C1-6烷基等，A为C6-14芳基或5至10成员杂环芳基，可选地取代等，B为C3-11环烷基等，D为C6-14芳基或5至10成员杂环芳基，可选地取代等。
• Synthesis of Benzylic Alcohols by Decarboxylative Hydroxylation
  作者：Qian Yu、Donglin Zhou、Yaoyue Liu、Xuejin Huang、Chunlan Song、Junjun Ma、Jiakun Li

  DOI：10.1021/acs.orglett.2c03741

  日期：2023.1.13

  demonstrate an efficient method for the decarboxylative hydroxylation of carboxylic acids with silver(I) as the catalyst and cerium ammonium nitrate as the oxidant and its utility in chemoselective late-stage functionalization of natural products and drug molecules. The chemoselectivity of this protocol arises from a benzylic nitrate intermediate that retards further oxidation and is hydrolyzed to the

  在此，我们展示了一种以银（I）为催化剂，硝酸铈铵为氧化剂的羧酸脱羧羟基化的有效方法，及其在天然产物和药物分子化学选择性后期功能化中的应用。该协议的化学选择性来自一种苄基硝酸盐中间体，它可以阻止进一步氧化并水解成最终的苄基醇产品。机理研究表明，羧酸银的容易氧化提供银（II）物质作为负责脱羧的中间氧化剂。
• US9403798B2
  申请人：——

  公开号：US9403798B2

  公开（公告）日：2016-08-02