N-hydroxy-1-naphthalenemethanamine | 98978-49-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-hydroxy-1-naphthalenemethanamine
• 英文别名: N-(naphthalen-1-ylmethyl)hydroxylamine
• CAS: 98978-49-5
• 化学式: C₁₁H₁₁NO
• mdl: MFCD18533374
• 分子量: 173.214
• InChiKey: MPCXCHXFWBBRME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-hydroxy-1-naphthalenemethanamine 在 (2S)-2-[二苯基[(三甲基硅酯)氧基]甲基]-吡咯烷 、 sodium tetrahydroborate 、 溶剂黄146 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 24.0h， 生成 (2'S,3'R,4'S,5'R)-1'-hydroxy-3'-(hydroxymethyl)-1-methyl-5'-(naphthalen-1-yl)-4'-phenylspiro[indoline-3,2'-pyrrolidin]-2-one
  参考文献：
  名称：

  靛红和叶黄素的位置选择性不对称形式（3 + 2）环加成反应。

  摘要：

  在另外的碱的存在下，通过亚胺鎓催化作用，开发了高度的区域，非对映体和对映体选择性对映体（3 + 2）的硝基亚硝基化物和α，β-不饱和醛的正环加成反应，提供了1'-羟基的光谱‐3,2'吡咯烷基吡咯并辛醇骨架。有趣的是，通过加入催化量的高氯酸锂和溴化铜（II），可以在硝酰基亚砜和巴豆醛之间的反应中很好地切换区域选择性。

  DOI：

  10.1002/adsc.201600805
• 作为产物：
  描述：

  1-naphtylaldehyde oxime 在 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 以61%的产率得到N-hydroxy-1-naphthalenemethanamine
  参考文献：
  名称：

  Synthesis and structure-activity relationships of naftifine-related allylamine antimycotics

  摘要：

  Naftifine (1) is the first representative of the new antifungal allylamine derivatives. Its biological activity is strictly bound to specific structural requirements that are unrelated to those of known antifungals. A tertiary allylamine function seems to be a prerequisite for activity against fungi. By systematic variation of the individual structural elements in 1, detailed structure-activity relationships are defined in which the phenyl ring is the structural feature permitting the widest variations. Versatile synthetic routes to allylamine derivatives and comparative biological data are presented.

  DOI：

  10.1021/jm00151a019

文献信息

• Highly Substituted 2,3-Dihydroisoxazoles by Et₃N-Catalyzed Tandem Reaction of Electron-Deficient 1,3-Conjugated Enynes with Hydroxylamines
  作者：Xiuzhao Yu、Bo Du、Kai Wang、Junliang Zhang

  DOI：10.1021/ol100490y

  日期：2010.4.16

  reaction of electron-deficient 1,3-conjugated enynes with hydroxylamines was developed which provided rapid, metal-free, and regioselective access to highly substituted multifunctionalized 2,3-dihydroisoxazoles under mild conditions. The reactions of 3-(2-arylethynyl)-4H-chromen-4-ones with hydroxylamines afford β-amino enones under the same reaction conditions.

  开发了一种Et 3 N催化的缺电子的1,3-共轭烯炔与羟胺的串联反应，该反应可在温和条件下快速，无金属和区域选择性地接近高度取代的多官能化2,3-二氢异恶唑。在相同的反应条件下，3-（2-芳基乙炔基）-4 H-铬烯-4-酮与羟胺的反应得到β-​​氨基烯酮。
• Asymmetric Construction of 2,3-Dihydroisoxazoles via an Organocatalytic Formal [3 + 2] Cycloaddition of Enynes with <i>N</i>-Hydroxylamines
  作者：Wenbo Li、Xiuzhao Yu、Zhenting Yue、Junliang Zhang

  DOI：10.1021/acs.orglett.6b01737

  日期：2016.8.19

  An organocatalytic asymmetric formal [3 + 2] cycloaddition of enynones with N-hydroxylamines has been described. A newly designed multifunctional organocatalyst was found to be highly effective, and the method allowed the synthesis of a variety of 2,3-dihydroisoxazoles in good yields with excellent enantioselectivity.

  已经描述了烯酮与N-羟胺的有机催化不对称的正式[3 + 2]环加成反应。发现一种新设计的多功能有机催化剂非常有效，该方法可以良好的收率和优异的对映选择性合成多种2,3-二氢异恶唑。
• Direct Asymmetric Aza-Vinylogous-Type Michael Additions of Nitrones from Isatins to Nitroalkenes
  作者：Gu Zhan、Ming-Lin Shi、Wei-Jia Lin、Qin Ouyang、Wei Du、Ying-Chun Chen

  DOI：10.1002/chem.201701290

  日期：2017.5.5

  Nitrones commonly act as 1,3‐dipoles and electrophiles to furnish valuable isoxazolidine and N‐hydroxyl products, respectively. They also can be converted to nitrone ylide species and undergo [3+2] formal cycloadditions to access N‐hydroxyl pyrrolidines. Here, asymmetric direct aza‐vinylogous‐type additions of nitrones from isatins to nitroalkenes are presented, catalyzed by a bifunctional thiourea‐tertiary

  亚硝酸盐通常充当1,3-偶极子和亲电子试剂，分别提供有价值的异恶唑烷和N-羟基产物。它们也可以转化为亚硝基叶立德物质，并经历[3 + 2]正式的环加成反应，从而获得N-羟基吡咯烷。在这里，介绍了一种由双功能素硫脲叔胺催化的从靛红到硝基烯烃的不对称直接氮杂-乙烯基型氮杂加成反应，从而提供具有扩展的碳骨架的高度官能化的硝酮，具有出色的立体选择性。值得注意的是，硝酮部分可以轻松除去，从而提供了烷基胺型物质的形式上不对称的α-官能化。而且，剩余的亲电硝酮基序使得随后的环切反应能够以高分子复杂性和多样性构建螺环产物，这可能在药物发现中具有潜在的应用。
• [3 + 3] Formal Cycloadditions of Nitrones from Isatins and Azaoxyallyl Cations for Construction of Spirooxindoles
  作者：Weijia Lin、Gu Zhan、Minglin Shi、Wei Du、Yingchun Chen

  DOI：10.1002/cjoc.201600864

  日期：2017.6

  A [3 + 3] formal cycloaddition reaction between in situ formed azaoxyallyl cations and nitrones from isatins has been developed, furnishing a spectrum of spiro[1,2,4‐oxadiazinan‐5‐one]oxindoles in good to excellent yields with excellent diastereoselectivity. This method provides direct and efficient access to potentially bioactive spirooxindoles incorporating a six‐membered heterocyclic scaffold.

  已经开发出[3 + 3]形式的原位形成的氮杂烯丙基烯丙基阳离子与靛红中的硝酮之间的正式环加成反应，从而提供了螺[1,2,4-氧杂二嗪-5-5]吲哚的光谱，其收率高至优异，具有非对映选择性。这种方法可直接有效地利用含有六元杂环支架的潜在具有生物活性的螺硫醇。
• Flame retarding resin composition
  申请人：——

  公开号：US20040077821A1

  公开（公告）日：2004-04-22

  Disclosed is a flame retarding resin composition comprising (A) one or more epoxy resins; (B) a hardener; and (C) a hardening accelerator, wherein the hardener of the component B is a phosphorus-containing compound represented by the following formula (I): 1 wherein each symbol is as defined below. The flame retarding resin composition of the present invention without adding halogen or other flame retardants has high flame retardancy and excellent heat resistance. The flame retarding resin composition of the present invention is suitably useful in the application of thermosetting resins, thermoplastic resins, bonding sheets, composite materials, laminated plates, printed circuit boards, copper foil adhesives, inks used for build-up process, semiconductor molding materials and the like.

  本发明公开了一种阻燃树脂组合物，该组合物包含(A)一种或多种环氧树脂；(B)一种固化剂；以及(C)一种硬化促进剂，其中成分 B 的固化剂是由下式(I)表示的含磷化合物： 1 其中各符号定义如下。本发明的阻燃树脂组合物不添加卤素或其他阻燃剂，具有高阻燃性和优异的耐热性。本发明的阻燃树脂组合物适用于热固性树脂、热塑性树脂、粘合片、复合材料、层压板、印刷电路板、铜箔粘合剂、用于堆积工艺的油墨、半导体成型材料等。