8-(Chloromethyl)-3',3'-dimethyl-6-nitro-1'-octadecylspiro[chromene-2,2'-indole] | 146904-81-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 8-(Chloromethyl)-3',3'-dimethyl-6-nitro-1'-octadecylspiro[chromene-2,2'-indole]
• CAS: 146904-81-6
• 化学式: C₃₇H₅₃ClN₂O₃
• 分子量: 609.292
• InChiKey: PSLLHABCTZJWSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14
• 重原子数：
  43
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  58.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-(Chloromethyl)-3',3'-dimethyl-6-nitro-1'-octadecylspiro[chromene-2,2'-indole] 、 benzo-10-aza-15-crown-5 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以61.6%的产率得到3',3'-Dimethyl-6-nitro-1'-octadecyl-8-(2,5,11,14-tetraoxa-8-azabicyclo[13.4.0]nonadeca-1(19),15,17-trien-8-ylmethyl)spiro[chromene-2,2'-indole]
  参考文献：
  名称：

  Syntheses of Negative Photochromic Crowned Spirobenzopyrans

  摘要：

  Two synthetic routes to negative photochromic spirobenzopyrans bearing a monoazacrown moiety at the 8-position were described and compared. Method B gives much higher total yield than method A.

  DOI：

  10.1080/00397910008087102
• 作为产物：
  描述：

  2,3,3-trimethyl-2,3-dihydro-1H-indole 在 sodium hydroxide 作用下， 以 苯 为溶剂， 反应 5.0h， 生成 8-(Chloromethyl)-3',3'-dimethyl-6-nitro-1'-octadecylspiro[chromene-2,2'-indole]
  参考文献：
  名称：

  Photochromic behaviour of surfactant spiro [2H-1-benzopyran-2,2′-[2,3]-dihydroindole]s (spiropyrans) adsorbed into clay interlayers

  摘要：

  Spiro[2H-1 -benzopyran-2,2'-[2,3]-dihydroindolels (abbreviated as spiropyrans) containing long omega-pyridinoalkyl chains have been intercalated into clay interlayers and studied to observe the photochromic characteristics of the resulting molecular assemblies. 1'-Octadecyl-3',3'-dimethyl-6-nitro-8-pyridinomethyl-(SP1801(+)), 1'-(10-pyridinodecyl)-3',3'-dimethyl-6-nitro- (SP10(+)00) and 1'-(10-pyridinodecyl)-3',3'-dimethyl-6-nitro-8-icosylcarbonyloxymethyl-spiropyrans (SP10(+) 22) were all quantitatively intercalated into the clay interlayer and exhibit normal photochromism in aqueous clay dispersions. Their thermal decolourations obey simple first-order kinetics and are about one-tenth as slow in clay dispersions and about one-hundredth as slow in clay films as that in bulk solution witho ut clay at 50 degrees C. However, 1',3',3 '-trimethyl-6-nitro-8-pyridinomethylspiropyran (SP0101(+)), a homologue without a long alkyl chain, exhibits inverse photochromism and its thermal decolouration undergoes two kinds of first-order kinetics in aqueous clay dispersions. These results are explicable in terms of the restricted conformational motions of the intercalated spiropyrans.

  DOI：

  10.1039/p29950001667

文献信息

• Liquid−Liquid Extraction of Alkali Metal Ions with Photochromic Crowned Spirobenzopyrans
  作者：Hidefumi Sakamoto、Takashi Yokohata、Tsuyoshi Yamamura、Keiichi Kimura

  DOI：10.1021/ac020003p

  日期：2002.6.1

  On the liquid−liquid extraction using 1,2-dichloroethane as an organic solvent, the crowned spirobenzopyrans exhibited textractability in the following order:  Li+ ≫ Na+ > K+ ≥ tetramethylammonium ion (TMA+), Li+ > Na+ ≫ K+ > TMA+, and Na+ > K+ ≫ Li+ > TMA+ for spirobenzopyran derivatives bearing monoaza-12-crown-4, 1; monoaza-15-crown-5, 2; and monoaza-18-crown-6, 3; respectively, under dark conditions. The ion selectivity of 1 depends on the metal-ion complexing ability of monoaza-12-crown-4. Even 2, which carries a 15-crown-5 moiety, showed Li+ selectivity because of the much stronger interaction of Li+ with the phenolate ion of the merocyanine form of 2 than that of Na+. The Na+ selectivity of 3 is also attributed to the ionic interaction with the phenolate ion of the merocyanine form, since the ionic interaction prefers Na+ to K+ regardless of the higher affinity of the 18-crown-6 ring itself to the latter ion. The Li+ extraction into the organic phase with 1 was enhanced by UV irradiation (300−400 nm), while some depression in the extraction was found by visible irradiation (>500 nm). The effect of visible irradiation on the Li+ complexing ability of 1 was also examined with electrospray ionization mass spectrometry.

  以 1,2-二氯乙烷为有机溶剂进行液-液萃取时，冠螺苯并吡喃按以下顺序表现出质地可萃取性：在黑暗条件下，单氮杂-12-冠-4（1）、单氮杂-15-冠-5（2）和单氮杂-18-冠-6（3）的螺苯并吡喃衍生物分别表现出 Li+ ≫ Na+ ≫ K+ ≥ 四甲基铵离子（TMA+）、Li+ ≫ Na+ ≫ K+ ≫ TMA+，以及 Na+ ≫ K+ ≫ Li+ ≫ TMA+。1 的离子选择性取决于单aza-12-冠-4 的金属离子络合能力。即使是含有 15-冠醚-5 分子的 2，也显示出 Li+ 的选择性，这是因为 Li+ 与 2 的经花青素形式的苯酚离子的相互作用要比 Na+ 强得多。3 的 Na+ 选择性也归因于与美拉德花青形式的苯酚离子之间的离子相互作用，因为离子相互作用更倾向于 Na+ 而不是 K+，尽管 18-crown-6 环本身对 K+离子的亲和力更高。紫外线照射（300-400 纳米）增强了 1 对有机相中 Li+ 的萃取，而可见光照射（>500 纳米）则抑制了萃取。此外，还利用电喷雾电离质谱法研究了可见光辐照对 1 的 Li+ 络合能力的影响。
• Photochromic behaviour of surfactant spiro [2H-1-benzopyran-2,2′-[2,3]-dihydroindole]s (spiropyrans) adsorbed into clay interlayers
  作者：Katsuhiko Takagi、Toshio Kurematsu、Yasuhiko Sawaki

  DOI：10.1039/p29950001667

  日期：——

  Spiro[2H-1 -benzopyran-2,2'-[2,3]-dihydroindolels (abbreviated as spiropyrans) containing long omega-pyridinoalkyl chains have been intercalated into clay interlayers and studied to observe the photochromic characteristics of the resulting molecular assemblies. 1'-Octadecyl-3',3'-dimethyl-6-nitro-8-pyridinomethyl-(SP1801(+)), 1'-(10-pyridinodecyl)-3',3'-dimethyl-6-nitro- (SP10(+)00) and 1'-(10-pyridinodecyl)-3',3'-dimethyl-6-nitro-8-icosylcarbonyloxymethyl-spiropyrans (SP10(+) 22) were all quantitatively intercalated into the clay interlayer and exhibit normal photochromism in aqueous clay dispersions. Their thermal decolourations obey simple first-order kinetics and are about one-tenth as slow in clay dispersions and about one-hundredth as slow in clay films as that in bulk solution witho ut clay at 50 degrees C. However, 1',3',3 '-trimethyl-6-nitro-8-pyridinomethylspiropyran (SP0101(+)), a homologue without a long alkyl chain, exhibits inverse photochromism and its thermal decolouration undergoes two kinds of first-order kinetics in aqueous clay dispersions. These results are explicable in terms of the restricted conformational motions of the intercalated spiropyrans.
• Syntheses of Negative Photochromic Crowned Spirobenzopyrans
  作者：Sheng-Hua Liu、Cheng-Tai Wu

  DOI：10.1080/00397910008087102

  日期：2000.3

  Two synthetic routes to negative photochromic spirobenzopyrans bearing a monoazacrown moiety at the 8-position were described and compared. Method B gives much higher total yield than method A.