1,3,3,4,5-pentamethylspironaphtho<2,1-b><1,4>oxazine> | 100463-19-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 1,3,3,4,5-pentamethylspironaphtho<2,1-b><1,4>oxazine>
• 英文别名: 1,3,3,4,5-pentamethylspironaphtoxazine>；1,3,3,4,5-Pentamethylspironaphth<2,1-b><1,4>oxazine>；1,3,3,4,5-pentamethylspironaphthoxazine>；1',3',3',4',5'-Pentamethylspiro[benzo[f][1,4]benzoxazine-3,2'-indole]
• CAS: 100463-19-2
• 化学式: C₂₄H₂₄N₂O
• 分子量: 356.467
• InChiKey: VZJJCOYOBXBMJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  27
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  24.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3,3,4,5-pentamethylspironaphtho<2,1-b><1,4>oxazine> 在 三乙烯二胺 作用下， 以 甲苯 为溶剂， 反应 5.83h， 生成 1-[(Z)-1,3,3,4,5-Pentamethyl-1,3-dihydro-indol-(2E)-ylidenemethylimino]-1H-naphthalen-2-one
  参考文献：
  名称：

  Eloy; Gay; Jardon, Journal de Chimie Physique et de Physico-Chimie Biologique, 1997, vol. 94, # 4, p. 683 - 706

  摘要：

  DOI：
• 作为产物：
  描述：

  1-[(E)-1,3,3,4,5-Pentamethyl-1,3-dihydro-indol-(2E)-ylidenemethylimino]-1H-naphthalen-2-one 以 solid matrix 为溶剂， 生成 1,3,3,4,5-pentamethylspironaphtho<2,1-b><1,4>oxazine>
  参考文献：
  名称：

  Coupling between Photochromism and Second-Harmonic Generation in Spiropyran- and Spirooxazine-Doped Polymer Films

  摘要：

  The photochemical ring opening of spiropyrans in polymethylmethacrylate (PMMA) host films in the presence of a high-voltage electric field (2-5 MV/cm) leads to a photo-orientation of photomerocyanines. Since photomerocyanines have rather high first-older hyperpolarizabilities, this photo-orientation leads to second-harmonic generation (SHG). The second-order susceptibility d(33) Of PMMA films doped with 6-nitro-1',3',3'-trimethylspiro[2H-1-benzopyran-2,2'-indoline] (25% w/w) has been measured at 10 pm/V. If a PMMA film doped with spiropyran and preoriented by corona poling at 90 degrees C is irradiated in the UV, an SHG signal of photomerocyanine is also observed as a result of a memory effect of the orientation of spiropyran molecules. The photoswitching of this nonlinear optical property can be inverted by visible light irradiation. Only partially reversible switching is observed because of a gradual light-induced disorientation of photomerocyanine dipoles. Photochemical quantum yields of the spiropyran reversible arrow photomerocyanine reaction have also been determined in PMMA for one system. Dipole moments and hyperpolarizabilities of closed and open forms have been calculated by semiempirical and finite field methods for an analogous system.

  DOI：

  10.1021/j100044a019

文献信息

• Photocromic nail enamel or varnish and the process for the preparation thereof
  申请人：ENICHEM SYNTHESIS S.p.A.

  公开号：EP0336193A2

  公开（公告）日：1989-10-11

  Photochromic nail enamel and varnish compositions are described which are characterized in that they contain a photochromically effective amount of at least one compound of general formula (I) e.g. 1,3,3,4,5- or 1,3,3,5,6-pentamethyl-spiro[indo­line-2,3′-[3H]-naphtho[2,1-b][1,4]oxazine], 1,3,3-tri­methyl-spiro[indoline-2,3′-[3H]naphtho[2,1-b][1,4]ox­azine], 1,3,3,4,5- or 1,3,3,5,6-pentamethyl-spiro[indo­line-6′-(1-piperidyl)-2,3′-[3H]naphtho[2,1-b][1,4]ox­axine], 1,3,3-trimethyl-spiro[indolien-6′-(1-piperidyl) -2,3′-[3H]naphtho[2,1-b][1,4]oxazine], 1,3,3-trimethyl-­spiro[indoline-6′-(1-morpholyl)-2,3′-[3H]naphtho[2,1-b] [1,4]oxazine], and 1,3,3-trimethyl-spiro[indoline-6′-­(1-piperidyl)-9′-methoxy-2,3′-[3H]naphtho[2,1-b][1,4] oxazine].

  所述光致变色指甲油和清漆组合物的特征在于，它们含有至少一种通式（I）化合物的光致变色有效量 例如1,3,3,4,5- or 1,3,3,5,6-pentamethyl-spiro[indo­line-2,3′-[3H]-naphtho[2,1-b][1,4]oxazine], 1,3,3-tri­methyl-spiro[indoline-2,3′-[3H]naphtho[2,1-b][1,4]ox­azine], 1,3,3,4,5- or 1,3,3,5,6-pentamethyl-spiro[indo­line-6′-(1-piperidyl)-2,3′-[3H]naphtho[2,1-b][1,4]ox­axine], 1,3,3-trimethyl-spiro[indolien-6′-(1-piperidyl) -2,3′-[3H]naphtho[2,1-b][1,4]oxazine], 1,3,3-trimethyl-­spiro[indoline-6′-(1-morpholyl)-2,3′-[3H]naphtho[2,1-b] [1,4]oxazine], and 1,3,3-trimethyl-spiro[indoline-6′-­(1-piperidyl)-9′-methoxy-2,3′-[3H]naphtho[2,1-b][1,4] oxazine].
• Eloy, D.; Escaffre, P.; Gautron, R., Journal de Chimie Physique et de Physico-Chimie Biologique, 1992, vol. 89, # 4, p. 897 - 914
  作者：Eloy, D.、Escaffre, P.、Gautron, R.、Jardon, P.

  DOI：——

  日期：——
• Gautron, Rene; Eloy, Dominique; Escaffre, Pascale, Bulletin des Societes Chimiques Belges, 1991, vol. 100, # 4, p. 315 - 328
  作者：Gautron, Rene、Eloy, Dominique、Escaffre, Pascale、Guglielmetti, Robert、Pottier, Eliane、Tardieu, Pascale

  DOI：——

  日期：——
• Oxidative degradation of organic photochromes
  作者：Vincenzo Malatesta、Mario Milosa、Roberto Millini、Luigi Lanzini、Piero Bortolus、Sandra Monti

  DOI：10.1080/10587259408037833

  日期：1994.5

  Photo-oxidation of some representative spiropyrans and spiro-oxazines does not seem to involve singlet oxygen O-2((1) Delta g). The photochromes rather behave, in the spiro and merocyanine form, as O-2((1) Delta g) quenchers. Only a methoxy-nitro benzopyran derivative was found to promote formation of singlet oxygen. Superoxide anion O-2(radical anion) is likely the activated oxygen species responsible for their oxidative photodegradation.
• Thermal and Photodegradation of Photochromic Spiroindolinenaphthooxazines and -pyrans:  Reaction with Nucleophiles. Trapping of the Merocyanine Zwitterionic Form
  作者：Vincenzo Malatesta、Carlo Neri、Maria Lucia Wis、Luciano Montanari、Roberto Millini

  DOI：10.1021/ja961784c

  日期：1997.4.1

  Adducts of the zwitterionic (ZW) form of merocyanine (MC) of five photochromic spirooxazines (SO) and spiropyrans (SP) have, for the first time, been prepared photochemically or thermally through a trapping reaction of metastable MC with trimethylsilyl cyanide (TMSCN) in dichloromethane. The adducts (ZWAs) form easily and are obtained in almost quantitative yields. X-ray diffraction analysis of ZWA of spirooxazine 2 shows that in the adduct the planes of the indolyl and naphthyl moieties form a ca. 29 degrees angle. The adduct crystallizes in the monoclinic space group P2(1)/n with a = 22.663(4) Angstrom, b = 8.234(1) Angstrom, c = 14.455(2) Angstrom, beta = 104.72(1)degrees, V = 2637.4(7) Angstrom(3), and D-calcd = 1.1476 Mg/m(3) for Z = 4. Least-squares refinement of the model based on 1986 reflections (F > 4 sigma(F)) converged to a final R = 0.066 and R-W = 0.068. ZWAs form through an unprecedented, clean, and regioselective Michael-type 1,6-addition of TMSCN to either a strongly polarized quinoidal MC form or its charge-separated zwitterionic limit structure. No evidence for the more common 1,2- and/or 1,4-addition has been found. The observed high reactivity of SOs and SPs with nucleophiles may contribute to the reported limited durability of these classes of photochromes.