N-(2-羟基丙基)-4-甲基苯磺酰胺 | 805338-72-1

• 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: N-(2-羟基丙基)-4-甲基苯磺酰胺
• 英文名称: N-[(2R)-2-hydroxypropyl]-4-methylbenzene-1-sulfonamide
• 英文别名: (R)-N-(2-Hydroxypropyl)-4-methylbenzenesulfonamide；N-[(2R)-2-hydroxypropyl]-4-methylbenzenesulfonamide
• CAS: 805338-72-1
• 化学式: C₁₀H₁₅NO₃S
• 分子量: 229.3
• InChiKey: RQOBKAQJZDLRFJ-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  74.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2-羟基丙基)-4-甲基苯磺酰胺 在 N-溴代丁二酰亚胺(NBS) 、 D(+)-10-樟脑磺酸 、 potassium carbonate 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 33.0h， 生成 (2R)-6-bromo-2-methyl-7-phenyl-4-tosyl-1,4-oxazepane
  参考文献：
  名称：

  Stereo- and Regioselective Synthesis of Polysubstituted Chiral 1,4-Oxazepanes

  摘要：

  The number of cyclic molecular scaffolds available to medicinal chemists remains limited, and simple structures such as oxazepanes are still made using multistep procedures, including a number of protection/deprotection steps and purifications. We report herein an expedient and efficient synthesis of chiral polysubstituted oxazepanes. The developed method relies on a regio- and stereoselective 7-endo cyclization through haloetherification. Mechanistic studies using a combination of computations and experiments confirmed the expected role of the asymmetry of the chiral bromonium intermediate on the haloetherification regioselectivity. Computations also suggested that the bromonium intermediate is formed with no transition state; hence, the stereoselectivity is controlled primarily by the conformation of the substrate. Applied to a set of 16 substrates, tetra- and pentasubstituted oxazepanes were prepared with good yields and moderate to excellent regio- and stereoselectivities.

  DOI：

  10.1021/jo3021715
• 作为产物：
  描述：

  异丙醇胺 、 对甲苯磺酰氯 在 sodium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 以94%的产率得到N-(2-羟基丙基)-4-甲基苯磺酰胺
  参考文献：
  名称：

  由溴离子介导的乙烯基芳烃的立体选择性双键双官能化。

  摘要：

  报道了使用溴离子介导的聚对苯二酚策略以分子间方式对苯乙烯基烯烃进行抗马尔科夫尼科夫双键氧化胺化反应。同位素标记研究证实了在频哪醇重排中苯基的迁移。

  DOI：

  10.1039/c3cc46003g

文献信息

• [EN] DIBENZOTHIOPHENE DERIVATIVES AS DNA- PK INHIBITORS<br/>[FR] DÉRIVÉS DE DIBENZOTHIOPHÈNE EN TANT QU'INHIBITEURS D'ADN-PK
  申请人：KUDOS PHARM LTD

  公开号：WO2010136778A1

  公开（公告）日：2010-12-02

  Compound formula I: wherein: X1 and X2 may be either (a) C and O, (b) N and N, or (c) C and NH, where the dotted bonds represents a double bond in the appropriate location; R1 and R2 are independently selected from hydrogen, an optionally substituted C1-7 alkyl group, an optionally substituted C3-20 heterocyclyl group, or an optionally substituted C5-20 aryl group, or may together form, along with the nitrogen atom to which they are attached, an optionally substituted heterocyclic ring having from 4 to 8 ring atoms; RN1 is selected from hydrogen and an optionally substituted C1-4 alkyl group; RC1 is selected from an optionally substituted C1-7 alkyl group, an optionally substituted C3-20 heterocyclyl group, or an optionally substituted C5-20 aryl group; or RN1 and RC1 may together form an optionally substituted C2-4 alkylene group.

  化合物公式I：其中：X1和X2可以是（a）C和O，（b）N和N，或（c）C和NH，其中点线代表适当位置的双键；R1和R2分别从氢，可选择的取代的C1-7烷基基团，可选择的取代的C3-20杂环基团，或可选择的取代的C5-20芳基基团中独立选择，或者可以与它们附着的氮原子一起形成具有4至8个环原子的可选择取代的杂环环；RN1从氢和可选择的取代的C1-4烷基基团中选择；RC1从可选择的取代的C1-7烷基基团，可选择的取代的C3-20杂环基团，或可选择的取代的C5-20芳基基团中选择；或RN1和RC1可以一起形成一个可选择取代的C2-4烷基烃基团。
• [EN] HOT MELT EXTRUDED SOLID DISPERSIONS CONTAINING A BCL2 INHIBITOR<br/>[FR] DISPERSIONS SOLIDES EXTRUDÉES À CHAUD CONTENANT UN INHIBITEUR DE BCL2
  申请人：NEWAVE PHARMACEUTICAL INC

  公开号：WO2021173523A1

  公开（公告）日：2021-09-02

  A pro-apoptotic solid dispersion comprises, a Bcl -2 family protein inhibitory compound of Formula A as defined herein, dispersed in a solid matrix that comprises (a) a pharmaceutically acceptable water-soluble polymeric carrier, and (b) a pharmaceutically acceptable surfactant. A process for preparing such a solid dispersion comprises subjecting to elevated temperature the compound of Formula A, the water-soluble polymeric carrier, and the surfactant to provide an extrudable semi-solid mixture; extruding the semi-solid mixture; and cooling the resulting extrudate to provide a solid matrix comprising the polymeric carrier, and the surfactant and having the compound dispersed in essentially non-crystalline form therein. The solid dispersion is suitable for oral administration to a subject in need thereof for treatment of a disease characterized by overexpression of one or more anti-apoptotic Bcl -2 family proteins, for example cancer or an immune or autoimmune disease.

  一种促凋亡的固体分散物包括本文所定义的Formula A的Bcl-2家族蛋白抑制化合物，分散在包括（a）药学上可接受的水溶性聚合物载体和（b）药学上可接受的表面活性剂的固体基质中。制备这种固体分散物的方法包括将Formula A的化合物、水溶性聚合物载体和表面活性剂置于高温下，以提供可挤出的半固体混合物；挤出半固体混合物；并冷却所得挤出物，以提供包含聚合物载体和表面活性剂的固体基质，并且其中的化合物以基本非晶形式分散其中。这种固体分散物适用于口服给予需要治疗由一个或多个抗凋亡Bcl-2家族蛋白过度表达所特征的疾病的患者，例如癌症或免疫或自身免疫疾病。
• Reagent-switch controlled metal-free intermolecular geminal diamination and aminooxygenation of vinylarenes
  作者：Pandur Venkatesan Balaji、Srinivasan Chandrasekaran

  DOI：10.1016/j.tet.2016.01.005

  日期：2016.2

  using hypervalent iodine reagent. A new m-CPBA mediated geminal aminooxygenation is also reported. A novel reagent-switch for the control of migrating group by controlling the two independent geminal addition paths is developed. Deuterium labelling studies and the control studies have provided unambiguous evidences for the phenyl migration and hydride migration in the oxidative geminal difunctionalization

  我们在这里报告了使用高价碘试剂进行芳基化的第一个一般方法，以及乙烯基芳烃的无分子间金属化，芳基化的氨基氧化。还报道了新的由m -CPBA介导的双链氨基氧化。开发了一种通过控制两个独立的双链加成路径来控制迁移基团的新型试剂开关。氘标记研究和对照研究提供了明确的证据，证明苯酚和氢化物迁移分别通过半频哪醇重排由PhI（OCOCF 3）2和m -CPBA介导的氧化双子双官能化过程中。
• Chiral‐Organotin‐Catalyzed Kinetic Resolution of Vicinal Amino Alcohols
  作者：Hui Yang、Wen‐Hua Zheng

  DOI：10.1002/anie.201909700

  日期：2019.11.4

  A highly efficient kinetic resolution of racemic amino alcohols has been achieved for the first time with a chiral tin catalyst. A chiral organotin compound with 3,4,5-trifluorophenyl groups at the 3,3'-positions of the binaphthyl framework enabled this transformation with excellent yield and high enantioselectivity. The process tolerates aryl- and alkyl-substituted amino alcohols and a variety of

  用手性锡催化剂首次获得了外消旋氨基醇的高效动力学拆分。在联萘骨架的3,3'-位置具有3,4,5-三氟苯基的手性有机锡化合物可实现出色的收率和高对映选择性，从而实现这种转化。该方法可耐受芳基和烷基取代的氨基醇以及多种其他底物，从而以高对映选择性和高达> 500的因子提供相应的产物。
• Zinc-Catalyzed Alkyne–Carbonyl Metathesis of Ynamides with Isatins: Stereoselective Access to Fully Substituted Alkenes
  作者：Chaoqun Ao、Xiaohan Yang、Shikun Jia、Xinfang Xu、Yanqiu Yuan、Dan Zhang、Wenhao Hu

  DOI：10.1021/acs.joc.9b02350

  日期：2019.12.6

  A zinc-catalyzed intermolecular alkyne-carbonyl metathesis reaction of ynamides with isatins followed by an amide to ester conversion has been developed, which produces the indolone derivatives with a fully substituted alkene species in good to high yields. The salient features of this reaction include the following: mild reaction conditions, an inexpensive zinc catalyst, a broad substrate scope, the

  已经开发出锌与酰胺的锌催化的分子间炔烃羰基复分解反应，然后由酰胺转化成酯，从而以良好或高收率生产了具有完全取代的烯烃的吲哚酮衍生物。该反应的显着特征包括：温和的反应条件，廉价的锌催化剂，广泛的底物范围，优异的区域控制和立体选择性，并且适合克规模。