O-benzyl-N-nonylhydroxylamine | 112712-23-9

• 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: O-benzyl-N-nonylhydroxylamine
• 英文别名: N-phenylmethoxynonan-1-amine
• CAS: 112712-23-9
• 化学式: C₁₆H₂₇NO
• 分子量: 249.396
• InChiKey: ZNLLISYHPPNKNY-UHFFFAOYSA-N

物化性质

• 沸点：
  339.9±35.0 °C(Predicted)
• 密度：
  0.925±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  18
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  O-benzyl-N-nonylhydroxylamine 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 乙酸乙酯 为溶剂， 反应 37.0h， 生成 (S)-2-(benzyloxy(nonyl)amino)-N-(2-oxotetrahydrofuran-3-yl)acetamide
  参考文献：
  名称：

  Immunosuppressive but Non-LasR-Inducing Analogues of the Pseudomonas aeruginosa Quorum-Sensing Molecule N-(3-Oxododecanoyl)-l-homoserine Lactone

  摘要：

  The Pseudomonas aeruginosa quorum-sensing molecule N-(3-oxododecanoyl)-l-homoserine lactone (1) is involved not only in bacterial activation but also in subversion of the host immune system, and this compound might thus be used as a template to design immunosuppressive agents, provided derivatives devoid of quorum-sensing activity could be discovered. By use of a leukocyte proliferation assay and a newly developed bioluminescent P. aeruginosa reporter assay, systematic modification of 1 allowed us to delineate the bacterial LasR-induction and host immunosuppressive activities. The main determinant is replacement of the methylene group proximal to the beta-ketoamide in the acyl chain of 1 with functions containing heteroatoms, especially an NH group. This modification can be combined with replacement of the homoserine lactone system in 1 with stable cyclic groups. For example, we found the simple compound N(1)-(5-chloro-2-hydroxyphenyl)-N(3)-octylmalonamide (25d) to be over twice as potent as 1 as an immune suppressor while displaying LasR-induction antagonist activity.

  DOI：

  10.1021/jm2001019
• 作为产物：
  描述：

  壬醛 、 O-苄基羟胺 在 溶剂黄146 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 7.0h， 以58%的产率得到O-benzyl-N-nonylhydroxylamine
  参考文献：
  名称：

  Immunosuppressive but Non-LasR-Inducing Analogues of the Pseudomonas aeruginosa Quorum-Sensing Molecule N-(3-Oxododecanoyl)-l-homoserine Lactone

  摘要：

  The Pseudomonas aeruginosa quorum-sensing molecule N-(3-oxododecanoyl)-l-homoserine lactone (1) is involved not only in bacterial activation but also in subversion of the host immune system, and this compound might thus be used as a template to design immunosuppressive agents, provided derivatives devoid of quorum-sensing activity could be discovered. By use of a leukocyte proliferation assay and a newly developed bioluminescent P. aeruginosa reporter assay, systematic modification of 1 allowed us to delineate the bacterial LasR-induction and host immunosuppressive activities. The main determinant is replacement of the methylene group proximal to the beta-ketoamide in the acyl chain of 1 with functions containing heteroatoms, especially an NH group. This modification can be combined with replacement of the homoserine lactone system in 1 with stable cyclic groups. For example, we found the simple compound N(1)-(5-chloro-2-hydroxyphenyl)-N(3)-octylmalonamide (25d) to be over twice as potent as 1 as an immune suppressor while displaying LasR-induction antagonist activity.

  DOI：

  10.1021/jm2001019

文献信息

• Bis(tri-n-butylstannyl)benzopinacolate: Preparation and use as a mediator of intermolecular free radical reactions
  作者：David J. Hart、Ramanarayanan Krishnamurthy、Lori M. Pook、Franklin L. Seely

  DOI：10.1016/s0040-4039(00)61484-3

  日期：1993.12

  Bis(tri-n-butylstannyl)benzopinacolate (2) serves as a thermal source of tri-n-butylstannyl radicals and mediates intermolecular coupling of selected alkyl halides to O-benzylformaldoxime and electron deficient olefins. A free radical non-chain mechanism is proposed for these reactions.

  双（三正丁基锡烷基）苯甲酸频哪酸酯（2）充当三正丁基锡烷基自由基的热源，并介导所选的烷基卤化物与O-苄基甲醛肟和缺电子烯烃的分子间偶联。提出了用于这些反应的自由基非链机制。
• Bis(trimethylstannyl)benzopinacolate-mediated intermolecular free-radical carbon-carbon bond-forming reactions: a new one-carbon homologation
  作者：David J. Hart、Franklin L. Seely

  DOI：10.1021/ja00213a051

  日期：1988.3

  Formation d'hydroxylamines organiques a partir d'hydrocarbures halogenes et de la benzyloxime du formaldehyde, par l'intermediaire du compose du titre comme source de radicaux stannyles

  Formation d'hydroxyamines Organiques a partir d'hydrocarbureshales et de la benzyloxime du formaldehyde, par l'intermediaire du compose du titre comme source de radicaux stannyles
• HART, DAVID J.;SEELY, FRANKLIN L., J. AMER. CHEM. SOC., 110,(1988) N 5, 1631-1633
  作者：HART, DAVID J.、SEELY, FRANKLIN L.

  DOI：——

  日期：——
• Immunosuppressive but Non-LasR-Inducing Analogues of the <i>Pseudomonas aeruginosa</i> Quorum-Sensing Molecule <i>N</i>-(3-Oxododecanoyl)-<scp>l</scp>-homoserine Lactone
  作者：Gopal P. Jadhav、Siri Ram Chhabra、Gary Telford、Doreen S. W. Hooi、Karima Righetti、Paul Williams、Barrie Kellam、David I. Pritchard、Peter M. Fischer

  DOI：10.1021/jm2001019

  日期：2011.5.12

  The Pseudomonas aeruginosa quorum-sensing molecule N-(3-oxododecanoyl)-l-homoserine lactone (1) is involved not only in bacterial activation but also in subversion of the host immune system, and this compound might thus be used as a template to design immunosuppressive agents, provided derivatives devoid of quorum-sensing activity could be discovered. By use of a leukocyte proliferation assay and a newly developed bioluminescent P. aeruginosa reporter assay, systematic modification of 1 allowed us to delineate the bacterial LasR-induction and host immunosuppressive activities. The main determinant is replacement of the methylene group proximal to the beta-ketoamide in the acyl chain of 1 with functions containing heteroatoms, especially an NH group. This modification can be combined with replacement of the homoserine lactone system in 1 with stable cyclic groups. For example, we found the simple compound N(1)-(5-chloro-2-hydroxyphenyl)-N(3)-octylmalonamide (25d) to be over twice as potent as 1 as an immune suppressor while displaying LasR-induction antagonist activity.