1,4-二氢-1,4-表亚氨基萘-9-羧酸叔丁酯 | 5176-28-3

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物 - 羧酸酯及其衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1,4-二氢-1,4-表亚氨基萘-9-羧酸叔丁酯
• 英文名称: N-(tert-butoxycarbonyl)-1,4-dihydro-1,4-iminonaphthalene
• 英文别名: tert-butyl 1,4-dihydro-1,4-epiminonaphthalene-9-carboxylate；Naphthalen-1,4-imine-9-carboxylic acid, 1,4-dihydro-, 1,1-dimethylethyl ester；tert-butyl 11-azatricyclo[6.2.1.02,7]undeca-2,4,6,9-tetraene-11-carboxylate
• CAS: 5176-28-3
• 化学式: C₁₅H₁₇NO₂
• 分子量: 243.305
• InChiKey: KTZZRAGNIAZODS-UHFFFAOYSA-N

物化性质

• 熔点：
  67-70 °C
• 沸点：
  342.1±42.0 °C(Predicted)
• 密度：
  1.177±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2925290090

上下游信息

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  1,2,3,4-四氢萘-1,4-亚氨-9-羧酸叔丁酯	tert-butyl 1,2,3,4-tetrahydro-1,4-epiminonaphthalene-9-carboxylate	5176-32-9	C15H19NO2	245.321
  ——	N-benzoyl-7-azabenzobicyclo[2.2.1]heptadiene	34353-23-6	C17H13NO	247.296
  ——	1,1-dimethylethyl (1aRS,2RS,7SR,7aSR)-1a,2,7,7a-tetrahydronaphth[2,3-b]oxiren-2,7-imine-8-carboxylate	512203-75-7	C15H17NO3	259.305
  ——	tert-butyl (1S,2S,3R,6S,7R,8R)-16-propan-2-ylidene-15-azapentacyclo[6.6.1.13,6.02,7.09,14]hexadeca-4,9,11,13-tetraene-15-carboxylate	72331-15-8	C23H27NO2	349.473
  ——	N-(tert-butoxycarbonyl)-1,2,3,4-tetrahydro-1,4-methanoisoquinoline	484698-23-9	C15H19NO2	245.321
  ——	tert-butyl (1R,2R,3S,10R,11R,12R)-15-oxo-18-azapentacyclo[10.3.2.13,10.02,11.04,9]octadeca-4,6,8,13,16-pentaene-18-carboxylate	72331-12-5	C22H23NO3	349.43
  1,4-二氢-萘-1,4-亚胺	1,4-dihydro-1,4-epiazano-naphthalene	5176-20-5	C10H9N	143.188
  ——	tert-butyl (1R,2R,3S,6R,7S,8S)-16-benzhydrylidene-15-azapentacyclo[6.6.1.13,6.02,7.09,14]hexadeca-4,9,11,13-tetraene-15-carboxylate	72331-14-7	C33H31NO2	473.615
  ——	Xoordcflaaztef-lzewcknjsa-	72376-88-6	C19H21NO3	311.381
  ——	Xoordcflaaztef-bofkiobhsa-	72331-16-9	C19H21NO3	311.381

反应信息

• 作为反应物：
  描述：

  1,4-二氢-1,4-表亚氨基萘-9-羧酸叔丁酯 在 palladium on activated charcoal 、 chloro(1,5-cyclooctadiene)rhodium(I) dimer 吡啶 、 (S,S)-(R,R)-C₂-ferriphos-tolyl 、 甲酸铵 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 为溶剂， 反应 63.42h， 生成 (1S,2S)-(2-苯甲酰氨基-1,2,3,4-四氢萘-1-基)氨基甲酸叔丁酯
  参考文献：
  名称：

  Enantioselective synthesis of chiral 1,2-diamines by the catalytic ring opening of azabenzonorbornadienes: application in the preparation of new chiral ligands

  摘要：

  In the presence of a rhodium catalyst (5 mol %) generated in situ from [Rh(cod)C]12 and (S,S')-(R,R')-C-2-ferriphos-tolyl, the asymmetric ring-opening reaction of N-Boc-azabenzonorbornadienes with dibenzylamine proceeded with excellent enantioselectivity (up to > 99% ee) to give the corresponding 1,2-diamine scaffolds in high yields. The sequential deprotection of the ring-opened products and treatment with tartaric acid gave the enantiomerically pure 1.2-diamine tartrate salts. These salts were used for the preparation of new chiral ligands Such as the salen-type ligands and Trost-type ligands, (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.12.024
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 4-二甲氨基吡啶 、 magnesium 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 10.0h， 生成 1,4-二氢-1,4-表亚氨基萘-9-羧酸叔丁酯
  参考文献：
  名称：

  EP3248968

  摘要：

  公开号：

文献信息

• Ruthenium-catalyzed [2+2] cycloadditions of bicyclic alkenes and ynamides
  作者：Karine Villeneuve、Nicole Riddell、William Tam

  DOI：10.1016/j.tet.2005.11.081

  日期：2006.4

  Ruthenium-catalyzed [2+2] cycloadditions between bicyclic alkenes and ynamides were investigated. The ynamide moiety was found to be compatible with the ruthenium-catalyzed cycloaddition conditions giving the corresponding cyclobutene cycloadducts in moderate to good yields (up to 97%). Diastereoselective cycloaddition utilizing chiral cyclic ynamides were also examined and a low to moderate level

  研究了钌催化的双环烯烃和乙酰胺之间的[2 + 2]环加成反应。发现该乙酰胺部分与钌催化的环加成条件相容，从而以中等至良好的产率（高达97％）给出了相应的环丁烯环加合物。还研究了利用手性环状炔酰胺的非对映选择性环加成反应，观察到低至中等水平的不对称诱导。
• Asymmetric Hydrophosphination of Heterobicyclic Alkenes: Facile Access to Phosphine Ligands for Asymmetric Catalysis
  作者：Zhiwu Lu、Haoyang Zhang、Zhiping Yang、Ning Ding、Ling Meng、Jun Wang

  DOI：10.1021/acscatal.8b04787

  日期：2019.2.1

  Asymmetric hydrophosphination is the most atomically economical and straightforward approach to the construction of chiral organophosphorus compounds. Good stereoselectivities have been achieved in asymmetric hydrophosphination of an electron-deficient C═C double bond, but substrates involving nonpolar C═C bonds remain difficult and are rarely tackled. Herein, we report asymmetric hydrophosphination

  不对称氢磷酸化是手性有机磷化合物构建中最原子经济且最直接的方法。在缺乏电子的C═C双键的不对称加氢磷化反应中已经获得了良好的立体选择性，但是涉及非极性C═C键的底物仍然很困难，而且很少解决。在本文中，我们报道了非电子活化的双键的非对称氢磷酸化，其立体控制程度非常高。该策略为制备高产率（高达99％的产率）和对映选择性（高达ee的99％）的叔膦提供了一个方便且广泛适用的平台。
• Asymmetric ring-opening of oxabenzonorbornadiene with amines promoted by a chiral iridium-monophosphine catalyst
  作者：Renshi Luo、Jianhua Liao、Ling Xie、Wenjun Tang、Albert S. C. Chan

  DOI：10.1039/c3cc46009f

  日期：——

  A new iridium-monophosphine catalyst is found to be efficient for asymmetric ring-opening of benzonorbornadiene with amines, providing a series of chiral substituted dihydronaphthalenes in high yields (up to 98%) and excellent enantioselectivities (>99%).

  发现一种新的铱单膦催化剂可有效地使苯并降冰片二烯与胺发生不对称开环，从而以高收率（高达98％）和出色的对映选择性（> 99％）提供一系列手性取代的二氢萘。
• Cobalt(III)-Catalyzed Intermolecular Carboamination of Propiolates and Bicyclic Alkenes via Non-Annulative Redox-Neutral Coupling
  作者：Yuelu Zhu、Feng Chen、Xinyang Zhao、Dingyuan Yan、Wanxiong Yong、Jing Zhao

  DOI：10.1021/acs.orglett.9b02016

  日期：2019.8.2

  cobalt(III)-catalyzed, redox-neutral, intermolecular carboamination of propiolates and bicyclic alkenes was developed. This non-annulative coupling strategy features atom economy, high regioselectivity, good yields, and functional groups tolerance. Such a carboamination reaction was applied to modified phenols from the corresponding phenols under mild conditions.

  开发了钴（II​​I）催化的丙酸酯和双环烯烃的氧化还原中性分子间碳氨基化反应。这种非环形的耦合策略具有原子经济，区域选择性高，产率高和官能团耐受性的特点。在温和的条件下，将这种碳氨化反应应用于来自相应酚的改性酚。
• Nickel-catalyzed regio- and diastereoselective intermolecular three-component coupling of oxabicyclic alkenes with alkynes and organoboronic acids
  作者：Subramaniyan Mannathan、Chien-Hong Cheng

  DOI：10.1039/c2cc38001c

  日期：——

  Reaction of oxabicyclic alkenes with alkynes and organoboronic acids in the presence of Ni(cod)(2), P(t-Bu)(3), and CsF in a binary solvent toluene-methanol (1 : 3) at 75 to 85 degrees C provided exo-5,6-disubstituted 7-oxanorbornene derivatives in good to excellent yields.

  Ni（cod）（2），P（t-Bu）（3）和CsF在二元溶剂甲苯-甲醇（1：3）中于75至85度下与氧杂双环烯烃与炔烃和有机硼酸的反应C以优异的产率提供了exo-5，6-二取代的7-氧杂降冰片烯衍生物。