4-((bromomethyl)sulfonyl)morpholine | 22457-12-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: 4-((bromomethyl)sulfonyl)morpholine
• 英文别名: Brommethansulfonsaeure-morpholid；Bromomethansulfonylmorpholin；4-bromomethanesulfonyl-morpholine；4-[(Bromomethyl)sulfonyl]morpholine；4-(bromomethylsulfonyl)morpholine
• CAS: 22457-12-1
• 化学式: C₅H₁₀BrNO₃S
• mdl: MFCD00033762
• 分子量: 244.109
• InChiKey: PUAIXHZIMYTCKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-((bromomethyl)sulfonyl)morpholine 在 六甲基磷酰三胺 、 氢氧化钾 、 sodium hydroxide 、 potassium hypochlorite 、 potassium chloride 、 四丁基硫酸氢铵 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 4-(trans-3-phenyl-oxiranesulfonyl)-morpholine
  参考文献：
  名称：

  New antifilarial agents. 1. Epoxy sulfonamides and ethynesulfonamides

  摘要：

  Two series of 2-substituted 1,2-epoxyethanesulfonamides 2 and ethynesulfonamides 5 were synthesized and evaluated for their antifilarial activity. The trans epoxides 2T were stereospecifically prepared by a Darzens reaction between aldehydes and halomethanesulfonamides. The cis isomers 2c were obtained from ethynesulfonamides 5 by semihydrogenation followed by KOCl epoxidation. 2-Substituted ethynesulfonamides 5 were synthesized from appropriate trans-ethenesulfonamides by a bromination/dehydrobromination sequence. These products, as well as several synthetic intermediates, were evaluated for antifilarial activity against Molinema dessetae either in vivo in its natural host, the rodent Proechimys oris, or in vitro by a new test using cultures of the infective larvae. Most of the epoxides 2T and acetylenic derivatives 5 bearing a 2-aryl substituent were active in vitro. Among these compounds, four epoxides 2T and one acetylenic derivative 5 showed marked macrofilaricidal activity in vivo without any microfilaricidal activity. The differences between the in vivo and in vitro results may be due, in part, to the low chemical stability of the epoxy sulfonamides 2T. Despite this limitation, the activities observed in this reliable animal model suggest further development and testing of both series 2T and 5 as macrofilaricides.

  DOI：

  10.1021/jm00395a010
• 作为产物：
  描述：

  吗啉 、 溴甲烷磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 4-((bromomethyl)sulfonyl)morpholine
  参考文献：
  名称：

  镍催化烯烃与 α-杂原子磷或硫烷基亲电试剂的对映聚合还原加氢烷基化反应

  摘要：

  近年来，通过使用外消旋仲烷基亲电试剂与有机金属试剂的过渡金属催化交叉偶联反应，对映收敛 C(sp3)-C(sp3) 键形成反应取得了重大进展。在此，我们报告了与杂原子相邻的烷基-烷基键的不对称构建的一般过程，即镍催化的烯烃与 α-杂原子磷或硫烷基亲电试剂的对映聚合还原加氢烷基化反应。包括使用容易获得的烯烃，该反应具有相当大的优势，如反应条件温和、底物范围广、官能团兼容性好，使其成为传统亲电-亲核交叉偶联反应的理想替代方案。

  DOI：

  10.1021/jacs.9b09415

文献信息

• Stereoconvergent Arylations and Alkenylations of Unactivated Alkyl Electrophiles: Catalytic Enantioselective Synthesis of Secondary Sulfonamides and Sulfones
  作者：Junwon Choi、Pablo Martín-Gago、Gregory C. Fu

  DOI：10.1021/ja506885s

  日期：2014.8.27

  controlling the stereochemistry of the sulfur-bearing carbon of such targets. In this report, we describe nickel-catalyzed stereoconvergent Negishi arylations and alkenylations of racemic α-bromosulfonamides and -sulfones that furnish the desired cross-coupling product in very good ee and yield for an array of reaction partners. Mechanistic studies are consistent with the generation of a radical intermediate

  开发用于生成对映体富集的磺酰胺和砜的有效方法是有机合成和药物化学等领域的重要目标；然而，关于直接催化不对称方法来控制此类目标的含硫碳的立体化学的报道相对较少。在本报告中，我们描述了镍催化的立体收敛 Negishi 芳基化和外消旋 α-溴磺酰胺和 - 砜的烯基化，它们以非常好的 ee 和产率为一系列反应伙伴提供所需的交叉偶联产物。机理研究与自由基中间体的产生一致，该中间体具有足够的寿命以扩散出溶剂笼并环化到侧链烯烃上。
• Mn-mediated reductive C(sp3)–Si coupling of activated secondary alkyl bromides with chlorosilanes
  作者：Liangliang Qi、Xiaobo Pang、Kai Yin、Qiu-Quan Pan、Xiao-Xue Wei、Xing-Zhong Shu

  DOI：10.1016/j.cclet.2022.03.070

  日期：2022.12

  solution to address this problem, but it typically relies on organometallic species. Herein, we report an Mn-mediated reductive C(sp3)–Si coupling to synthesize these compounds from alkyl and silyl electrophiles. This approach avoids the requirement for activation of Si–Cl by transition metals and thus allows for the coupling of various common chlorosilanes. The reaction proceeds under mild conditions

  仲烷基硅烷的构建在合成领域是一个具有挑战性的课题。交叉偶联为解决这个问题提供了一种实用的解决方案，但它通常依赖于有机金属物质。在此，我们报道了一种 Mn 介导的还原性 C(sp 3 )-Si 偶联以从烷基和甲硅烷基亲电试剂合成这些化合物。这种方法避免了过渡金属对 Si-Cl 活化的要求，因此可以偶联各种常见的氯硅烷。反应条件温和，官能团相容性好。该方法提供了获得α-甲硅烷基化有机磷和砜的途径，其范围与从已建立的方法中获得的范围互补。
• BRIENE, MARIE-JOSEPHE;VARECH, DANIEL;LECLERCQ, MARTINE;JACQUES, JEAN;BADE+, J. MED. CHEM., 30,(1987) N 12, 2232-2239
  作者：BRIENE, MARIE-JOSEPHE、VARECH, DANIEL、LECLERCQ, MARTINE、JACQUES, JEAN、BADE+

  DOI：——

  日期：——
• ——
  作者：JACQUES J.、 VARECH D.、 BRIENNE M. -J.、 GAYRAL PH.

  DOI：——

  日期：——