N-benzyl-diethanolamine N-oxide | 15831-62-6

• 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: N-benzyl-diethanolamine N-oxide
• 英文别名: N,N-Di-(2-hydroxyethyl)-N-benzylaminooxid；2,2'-(benzyl-oxy-azanediyl)-bis-ethanol；N-benzyl-2-hydroxy-N-(2-hydroxyethyl)ethanamine oxide
• CAS: 15831-62-6
• 化学式: C₁₁H₁₇NO₃
• 分子量: 211.261
• InChiKey: UTHKQMVYZRWSKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  58.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-benzyl-diethanolamine N-oxide 在 rubidium carbonate 、 4-二甲氨基吡啶 、 C₂₇H₃₃N₄O₃⁽¹⁺⁾*BF₄^(1-) 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 氯苯 为溶剂， 反应 24.0h， 生成 (E)-2-(benzoyloxy)-N-benzyl-N-(2-((3-(4-fluorophenyl)acryloyl)oxy)ethyl) ethan-1-amine oxide
  参考文献：
  名称：

  10.1002/anie.202404979

  摘要：

  AbstractThe control of noncarbon stereogenic centers is of profound importance owing to their enormous interest in bioactive compounds and chiral catalyst or ligand design for enantioselective synthesis. Despite various elegant approaches have been achieved for construction of S‐, P‐, Si‐ and B‐stereocenters over the past decades, the catalyst‐controlled strategies to govern the formation of N‐stereogenic compounds have garnered less attention. Here, we disclose the first organocatalytic approach for efficient access to a wide range of nitrogen‐stereogenic compounds through a desymmetrization approach. Intriguingly, the pro‐chiral remote diols, which are previously not well addressed with enantiocontrol, are well differentiated by potent chiral carbene‐bound acyl azolium intermediates. Preliminary studies shed insights on the critical importance of the ionic hydrogen bond (IHB) formed between the dimer aggregate of diols to afford the chiral N‐oxide products that feature a tetrahedral nitrogen as the sole stereogenic element with good yields and excellent enantioselectivities. Notably, the chiral N‐oxide products could offer an attractive strategy for chiral ligand design and discovery of potential antibacterial agrochemicals.

  DOI：

  10.1002/anie.202404979
• 作为产物：
  描述：

  2,2’-(苄基亚氨基)二乙醇 在 esterase from porcine liver 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 phosphate buffer 、 氯仿 、 苯 为溶剂， 反应 51.5h， 生成 N-benzyl-diethanolamine N-oxide
  参考文献：
  名称：

  N-手性叔胺氧化物的对映选择性制备

  摘要：

  我们发现PLE可以用作手性叔胺N-氧化物去对称化的有效催化剂，并证明PLE可有效地将它们水解，以中等至良好的收率提供高达99％ee的N-色氨酸叔胺氧化物。

  DOI：

  10.1016/j.tetlet.2007.07.183

文献信息

• TARGETED NITROXIDE AGENTS
  申请人：Wipf Peter

  公开号：US20100035869A1

  公开（公告）日：2010-02-11

  Provided herein are compositions and related methods useful for free radical scavenging, with particular selectivity for mitochondria. The compounds comprise a nitroxide-containing group attached to a mitochondria-targeting group. The compounds can be cross-linked into dimers without loss of activity. Also provided herein are methods, for preventing, mitigating and treating damage caused by radiation. The method comprises delivering a compound, as described herein, to a patient in an amount and dosage regimen effective to prevent, mitigate or treat damage caused by radiation.

  本文提供了一种对自由基清除有用的组合物和相关方法，具有特定选择性作用于线粒体。这些化合物包括一个连接到线粒体靶向基团的亚硝基含有基团。这些化合物可以交联成二聚体而不丧失活性。本文还提供了一种用于预防、缓解和治疗辐射引起的损伤的方法。该方法包括向患者输送一种如本文所述的化合物，以有效地预防、缓解或治疗辐射引起的损伤。
• A mild and efficient cyanosilylation of ketones catalyzed by a Lewis acid–Lewis base bifunctional catalyst
  作者：Yongcun Shen、Xiaoming Feng、Yan Li、Guolin Zhang、Yaozhong Jiang

  DOI：10.1016/s0040-4020(03)00908-6

  日期：2003.7

  new family of bifunctional catalysts (N-oxides–Ti(OiPr)4 (2:1)) containing a Lewis acid and a Lewis base was developed and applied to the catalytic cyanosilylation of ketones. Utilizing rac((1R,2S) and (1S,2R))-1-(2′-pyridylmethyl)-2-diphenylhydroxymethylpyrrolidine N-oxide–titanium (2:1) complex and N-benzyl-diethanolamine N-oxide–titanium (2:1) complex as catalysts, the cyanosilylation products were

  开发了一种新的含路易斯酸和路易斯碱的双功能催化剂（N-氧化物-Ti（O i Pr）4（2：1）），并将其用于酮的氰基催化硅烷化反应。利用rac（（1 R，2 S）和（1 S，2 R））-1-（2'-吡啶基甲基）-2-二苯基羟甲基吡咯烷N-氧化物-钛（2：1）络合物和N-苄基-二乙醇胺N用氧化钛-钛（2：1）络合物作为催化剂，氰基硅烷化产物的产率为42-97％。基于实验现象和动力学研究，提出了催化循环以解释这些催化剂的显着活性。研究表明，rac（（1 R，2 S）和（1 S，2 R））-1-（2'-吡啶基甲基）-2-二苯基羟甲基吡咯烷N-氧化物-钛（2：1）络合物和N-苄基-二乙醇胺ñ氧化物-钛（2：1）复合物应促进经由由钛和TMSCN由所述酮的一个双重激活反应ñ氧化物。
• A Mild and Efficient Cyanosilylation of Ketones Using In Situ Generated N-oxides-Ti(iPrO)4 Complexes as Catalysts
  作者：Yongcun Shen、Xiaoming Feng、Yan Li、Guolin Zhang、Yaozhong Jiang

  DOI：10.1055/s-2002-25370

  日期：——

  The addition of TMSCN to ketones catalyzed by complex of racemic N-(2′-pyridylmethyl)-2-diphenylhydroxymethyl-pyrrolidine N-oxide (rac-1) or N-benzyl-N,N-dihydroxyethylamine N-oxide and Ti(iPrO)4 affords the racemic O-TMS cyanohydrins in good to excellent isolated yields (up to 97%) under mild reaction conditions.

  在外消旋 N-(2′-吡啶基甲基)-2-二苯基羟甲基吡咯烷 N-氧化物（rac-1）或 N-苄基-N,N-二羟乙基胺 N-氧化物与 Ti(iPrO)4 的络合物催化下，TMSCN 与酮的加成反应可在温和的反应条件下以良好到极佳的分离产率（高达 97%）得到外消旋 O-TMS 氰基水合物。
• TOPICAL FORMULATIONS OF TARGETED NITROXIDE AGENTS
  申请人：Falo, JR. Louis D.

  公开号：US20120207687A1

  公开（公告）日：2012-08-16

  A method for preventing or treating skin damage in a radiotherapy subject, comprising topically administering to the subject a composition that includes a therapeutically effective amount at least one targeted nitroxide agent and at least one additional ingredient.

  一种用于预防或治疗放疗受试者皮肤损伤的方法，包括将至少一种靶向亚硝酰胺试剂和至少一种其他成分的治疗有效剂量的组合物局部施用于受试者的皮肤。
• USE OF TARGETED NITROXIDE AGENTS IN PREVENTING, MITIGATING AND TREATING RADIATION INJURY
  申请人：Wipf Peter

  公开号：US20110172214A1

  公开（公告）日：2011-07-14

  Provided herein are compositions and related methods useful for free radical scavenging, with particular selectivity for mitochondria. The compounds comprise a nitroxide-containing group attached to a mitochondria-targeting group. The compounds can be cross-linked into dimers without loss of activity. Also provided herein are methods, for preventing, mitigating and treating damage caused by radiation. The method comprises delivering a compound, as described herein, to a patient in an amount and dosage regimen effective to prevent, mitigate or treat damage caused by radiation.

  本文提供了一种有用于自由基清除的组合物和相关方法，特别是对线粒体的选择性。该化合物包括连接到线粒体靶向基团的亚硝基含有基团。该化合物可以交联成二聚体而不失去活性。本文还提供了一种方法，用于预防、缓解和治疗放射性损伤。该方法包括将上述所述的化合物以有效的剂量和用药方案输送给患者，以预防、缓解或治疗放射性损伤。