萘环氧化物 | 17180-88-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 萘环氧化物
• 英文名称: naphthalene 1,2-oxide
• 英文别名: naphthalene 1,2-epoxide；naphthalene-1,2-oxide；naphthalene epoxide；naphthalene oxide；1,2-epoxy-1,2-dihydro-naphthalene；1,2-Dihydro-1,2-epoxynaphthalin；1a,7b-dihydronaphtho[1,2-b]oxirene
• CAS: 17180-88-0
• 化学式: C₁₀H₈O
• 分子量: 144.173
• InChiKey: XQIJIALOJPIKGX-UHFFFAOYSA-N

物化性质

• 熔点：
  42-46 °C
• 沸点：
  264.1±19.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

ADMET

代谢

萘-1,2-氧化物是萘的人类已知代谢物。

Naphthalene-1,2 Expodation is a known human metabolite of naphthalene.

来源:NORMAN Suspect List Exchange

反应信息

• 作为反应物：
  描述：

  萘环氧化物 在 高氯酸 、 sodium hydroxide 作用下， 以 2,2,2-三氟乙醇 、 水 为溶剂， 反应 5.17h， 生成 2-苯基硫烷基萘
  参考文献：
  名称：

  芳烃离子的超芳香族稳定：2-取代的1,2-二氢-1-萘酚的酸催化脱水

  摘要：

  对于酸催化脱水速率常数顺-2-取代的1,2-二氢萘由塔夫脱关系日志良好相关ķ = -0.49 - 8.8σ我，与OH和OME轻微负偏差。相比之下，反式取代基与σI的相关性较弱，并且在大多数情况下，其反应比顺式异构体慢。该行为与速率确定的2-取代碳阳离子（萘离子）中间体的形成一致，该中间体对顺式反应物具有2-CH键，其取向适合与电荷中心超共轭。对于反式异构体2-取代基本身在阳离子的最初形成的构型中定向为超共轭。有人认为，ķ顺/ ķ反式率比率的取代基（ME，8.4;卜吨，12.7; pH值，3.8; NH 3 +，160; OH，440）反映他们hyperconjugating能力相对于氢。对于已知的（RS，N 3）或怀疑的（EtSO，EtSO 2）通过π或σ邻基效应稳定阳离子的取代基，观察到反式异构体的反应更快。Taft相关性好表明顺式学生的反应正常，仅因其感应作用而有所区别。反式异构体的较

  DOI：

  10.1021/jo2020483
• 作为产物：
  描述：

  1,2-二氢萘 在 N,N’-双(亚水杨基)-1,2-乙二胺-锰(II) 双氧水 作用下， 以 二氯甲烷 为溶剂， 生成 萘环氧化物
  参考文献：
  名称：

  Catalase and Epoxidation Activity of Manganese Salen Complexes Bearing Two Xanthene Scaffolds

  摘要：

  A series of manganese Hangman salen ligand platforms functionalized by tert-butyl groups in the 3 and 3' positions using the Suzuki cross-coupling methodology are presented. The Hangman platforms support multielectron chemistry mediated by proton-coupled electron transfer (PCET), as demonstrated by their ability to promote the catalytic disproportionation of hydrogen peroxide to oxygen and water via a high-valent metal oxo. The addition of the steric groups to the salen macrocycle leads to enhanced catalase activity by circumventing side reactions that sequester the catalyst off pathway. The stereochemistry imposed by the cyclohexanediamine backbone of the salen platform is revealed by the epoxidation of 1,2-dihydronapthalene by a variety of oxidants. Improved enantiomeric excess and catalase activity as compared to sterically unmodified counterparts establishes the efficacy of the tert-butyl groups in promoting PCET catalysis on the Hangman platform.

  DOI：

  10.1021/ja070358w

文献信息

• 1,2,4-Triazole derivatives
  申请人：IMPERIAL CHEMICAL INDUSTRIES PLC

  公开号：EP0275704A1

  公开（公告）日：1988-07-27

  A thiophene, furan or tetrahydrofuran triazolyl derivative having the general formula (I) or (II) : and stereoisomers thereof, wherein R¹ is tertiary butyl, which may be optionally substituted with one or more halogen atoms; R² is the group :     -(CH₂)n-Z or      -CH=CH-X or      -C≡C-Z where n is an integer from 0 to 3 and Z is an optionally substituted thiophene, furan, or tetrahydrofuran ring; and X is an optionally substituted thiophene or tetrahydro­furan ring; and R³ is hydrogen or an alkyl group containing from 1 to 4 carbon atoms; and salts, esters and metal complexes of the compound of formula (I) and (II) wherein R³ is hydrogen.

  一种具有通式(I)或(II)的噻吩、呋喃或四氢呋喃三唑基衍生物及其立体异构体，其中R¹为三丁基，可以选择性地用一个或多个卤素原子取代；R²为基团：-(CH₂)n-Z或-CH=CH-X或-C≡C-Z，其中n为0到3的整数，Z为可选择性取代的噻吩、呋喃或四氢呋喃环；X为可选择性取代的噻吩或四氢呋喃环；R³为氢或含有1至4个碳原子的烷基基团；以及通式(I)和(II)化合物的盐、酯和金属配合物，其中R³为氢。
• Unprecedented catalytic enantioselective trapping of arene oxides with dialkylzinc reagentsElectronic supplementary information (ESI) available: experimental details. See http://www.rsc.org/suppdata/cc/b1/b108541g/
  作者：Fabio Bertozzi、Paolo Crotti、Federica Del Moro、Ben L. Feringa、Franco Macchia、Mauro Pineschi

  DOI：10.1039/b108541g

  日期：2001.12.19

  The first catalytic enantioselective trapping of symmetrical and racemic arene oxides with organometallic reagents is reported.

  首次报道了用有机金属试剂催化对称和外消旋炔氧化物的对映选择性捕集。
• Kinetic and Thermodynamic Stability of Naphthalene Oxide and Related Compounds. A Comparative Microcalorimetric and Computational (DFT) Study
  作者：Peter Brandt、Zhi Sheng Jia、Alf Thibblin

  DOI：10.1021/jo025953p

  日期：2002.11.1

  naphthalene 1,2-oxide (5) in highly aqueous media to give naphthols has been measured by heat-flow microcalorimetry. The reaction enthalpy of this aromatization reaction was measured as DeltaH = -51.3 +/- 1.7 kcal mol(-)(1). The unexpectedly low reactivity of naphthalene oxide is suggested to be due to an unusually large thermodynamic stability. A crude estimate of the stabilization effect, approximately 1 kcal

  已经通过热流微量热法测量了在高水介质中萘1,2-氧化物（5）的酸催化开环反应生成萘的动力学。测量该芳构化反应的反应焓为ΔH＝ -51.3 +/- 1.7kcal mol（-）（1）。氧化萘的异常低的反应性被认为是由于异常大的热力学稳定性所致。通过使用测量的结构相关底物的反应焓作为参考，可以得到大约1 kcal mol（-）（1）（不是明显的稳定化）稳定作用的粗略估计。通过使用B3LYP杂化功能通过计算得到更大的值（2.7 kcal mol（-）（1）），该功能经溶剂化能量校正后得自半经验AM1 / SM2计算。从同共轭稳定和同芳香性方面讨论了这种作用的起源。实验测得的活化自由能与计算出的碳正离子形成焓之间存在良好的线性关系（斜率= 0.63）。
• Heterocyclic tertiary alcohols
  申请人：IMPERIAL CHEMICAL INDUSTRIES PLC

  公开号：EP0409418A1

  公开（公告）日：1991-01-23

  Heterocyclic tertiary alcohol compounds useful as plant growth regulators have the general formula (I) : wherein n is an integer which is 0 or 1; X is S or O; R¹ is an optionally substituted secondary or tertiary alkyl group or an optionally substituted cycloalkyl or alkylcycloalkyl group containing a total of from 3 to 7 carbon atoms; R² is a group : -(CH₂)a-C≡C-A (II) or -(CH₂)b-CH=CH-A (III) or -(CH₂)c-A (IV) or -CH₂-O-(CH₂)d-A (V) wherein A is an optionally substituted aryl group, a, b and d are integers from 0 to 2 and c is an integer from 0 to 4; or R² is an optionally halo-substituted alkyl, cycloalkyl, cycloalkylalkyl alkylcycloalkyl group or alkylcycloalkylalkyl, or is an optionally halo-substituted alkenyl, cycloalkenyl, cycloalkenylalkyl, alkylcycloalkenyl or alkylcycloalkenylalkyl group, or is an optionally halo-substituted alkynyl group each of said groups containing a total of from 4 to 8 carbon atoms; R³ is hydrogen, an alkyl group containing from 1 to 4 carbon atoms or an alkenyl or alkynyl group containing from 3 to 4 carbon atoms.

  具有植物生长调节剂作用的杂环三级醇化合物的一般公式为（I）：其中n是0或1的整数；X是S或O; R¹是一个可选的取代的二级或三级烷基或一个可选的取代的总碳原子数为3到7的环烷基或烷基环烷基基团；R²是一个基团：-(CH₂)a-C≡C-A（II）或-(CH₂)b-CH=CH-A（III）或-(CH₂)c-A（IV）或-CH₂-O-(CH₂)d-A（V）其中A是一个可选的取代的芳基基团，a、b和d是从0到2的整数，c是从0到4的整数；或R²是一个可选的卤代烷基、环烷基、环烷基烷基、烷基环烷基烷基基团或烷基环烷基烷基烷基基团，或是一个可选的卤代烯基、环烯基、环烯基烷基、烷基环烯基或烷基环烯基烷基基团，或是一个可选的卤代炔基基团，每个所述的基团都含有4到8个碳原子；R³是氢、含有1到4个碳原子的烷基基团或含有3到4个碳原子的烯基或炔基基团。
• SILYLATION OF AROMATIC HETEROCYCLES BY EARTH ABUNDANT TRANSITION-METAL-FREE CATALYSTS
  申请人：CALIFORNIA INSTITUTE OF TECHNOLOGY

  公开号：US20160046653A1

  公开（公告）日：2016-02-18

  The present invention describes chemical systems and methods for silylating aromatic organic substrates, said system or method comprising or consisting essentially of a mixture of (a) at least one organosilane and (b) at least one strong base, the definition of strong base now also including hydroxide, especially KOH, said system being preferably, but not necessarily substantially free of a transition-metal compound, and said methods comprising contacting a quantity of the organic substrate with a mixture of (a) at least one organosilane and (b) at least one strong base, under conditions sufficient to silylate the aromatic substrate; wherein said system is substantially free of a transition-metal compound.

  本发明描述了用于硅烷化芳香有机基质的化学系统和方法，该系统或方法包括或基本上由以下混合物组成：（a）至少一种有机硅烷和（b）至少一种强碱，强碱的定义现在还包括氢氧化物，特别是KOH，该系统最好是但不一定完全不含过渡金属化合物，该方法包括将有机基质的数量与（a）至少一种有机硅烷和（b）至少一种强碱的混合物接触，在足够的条件下硅烷化芳香基质；其中所述系统基本上不含过渡金属化合物。