2-(2-butynyloxymethyl)-1-{2-[2-(2-butynyloxymethyl)-1-naphthyl]-1-ethynyl}naphthalene | 207673-35-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(2-butynyloxymethyl)-1-{2-[2-(2-butynyloxymethyl)-1-naphthyl]-1-ethynyl}naphthalene
• 英文别名: 2-(But-2-ynoxymethyl)-1-[2-[2-(but-2-ynoxymethyl)naphthalen-1-yl]ethynyl]naphthalene
• CAS: 207673-35-6
• 化学式: C₃₂H₂₆O₂
• 分子量: 442.557
• InChiKey: ZYDANTCHBQKABW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-butynyloxymethyl)-1-{2-[2-(2-butynyloxymethyl)-1-naphthyl]-1-ethynyl}naphthalene 在 carbon monoxide,cobalt,cyclopenta-1,3-diene 三苯基膦 作用下， 以 癸烷 为溶剂， 反应 3.0h， 以64%的产率得到10,11-dimethyl-7,9,12,14-tetrahydrobenzo[c]naphtho[2,1-c]naphtho[1'',2'':5',6']oxepino[3',4':5,6]benzo[e]oxepin
  参考文献：
  名称：

  A Novel Strategy for the Synthesis of Molecules with Helical Chirality. Intramolecular [2 + 2 + 2] Cycloisomerization of Triynes under Cobalt Catalysis

  摘要：

  A straightforward synthetic approach to a new das's of molecules with helical chirality has been developed involving an intramolecular [2 + 2 + 2] cycloisomerization of triynes under CpCo(CO)(2)/ PPh3 catalysis. The cyclization reaction is promoted by visible light irradiation. Starting from 1,2-diarylacetylenes with two terminal or methyl-substituted tethered acetylene moieties (1a,b,4, 5, and 7), the target products (8a,b, 11, 12, and 14) are obtained in 64-89% yield. The triynes bearing terminal trimethylsilyl groups (Ic, 2, and 3) are less reactive and afford the products (8c, 9a,b, and 10) in 23-71% yield. The ability of the trimethylsilylated derivatives to cycloisomerize strongly depends on the tether length. The cyclized products (8-14) with five, six, and seven ortho-fused rings structurally resemble classical helicenes. Several representatives (8b, 11, 12, and 14) have been resolved into enantiomers by HPLC on a chiral column. Thus, the methodology exhibits a considerable versatility and allows the preparation of a variety of helical objects.

  DOI：

  10.1021/jo9801263
• 作为产物：
  描述：

  1-iodo-2-hydroxymethylnaphtalene 在 copper(l) iodide 、 四(三苯基膦)钯 哌啶 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 2-(2-butynyloxymethyl)-1-{2-[2-(2-butynyloxymethyl)-1-naphthyl]-1-ethynyl}naphthalene
  参考文献：
  名称：

  邻位取代的芳基卤化物与炔烃的偶联反应。官能化的1-萘基，1-（1-萘基）-2-苯基-和1,2-双（1-萘基）乙炔的合成

  摘要：

  在Pd（PPh 3）4或催化作用下，研究了2-官能化的1-萘基卤化物与气态乙炔，（三烷基甲硅烷基）乙炔基和芳基乙炔的偶合反应以制备1-萘基-，1-（1-萘基）-2-苯基- ，和1,2-双（1-萘基）乙炔与各种邻位的取代基，即，对-CH 3，-CH 2 OH，-CO 2 Me和-CH 2 OCH 2 CCCH 3个基团。通过改变芳基卤化物中的卤素原子，溶剂，（三烷基甲硅烷基）乙炔中的烷基和催化剂（Pd（O）vs.）。在具有连接的炔烃单元的1-萘碘化物的情况下，已观察到偶联可与级联的分子内Heck型反应竞争。已经讨论了β-消除氢化钯物种的机理。已经发现带有-CO 2 Me基团的1-萘基溴易于被溶剂进行亲核芳族取代。已经显示，不对称的1-（1-萘基）-2-苯基乙炔衍生物的成功合成关键取决于芳基卤化物/芳基乙炔的组合。

  DOI：

  10.1016/s0040-4020(98)00655-3

文献信息

• Coupling reactions of ortho-substituted aryl halides with alkynes. The synthesis of functionalized 1-naphthyl-, 1-(1-naphthyl)-2-phenyl-, and 1,2-bis(1-naphthyl)acetylenes
  作者：Irena G. Stará、Ivo Starý、Adrian Kollárovič、Filip Teplý、David Šaman、Pavel Fiedler

  DOI：10.1016/s0040-4020(98)00655-3

  日期：1998.9

  Coupling of 2-functionalized 1-naphthyl halides with gaseous acetylene, (trialkylsilyl)acetylenes, and aryl acetylenes under Pd(PPh3)4 or catalysis has been investigated to prepare 1-naphthyl-, 1-(1-naphthyl)-2-phenyl-, and 1,2-bis(1-naphthyl)acetylenes with various ortho substituents, i.e., the -CH3, -CH2OH, -CO2Me, and -CH2OCH2CCCH3 groups. The reaction conditions have been optimized (yields up

  在Pd（PPh 3）4或催化作用下，研究了2-官能化的1-萘基卤化物与气态乙炔，（三烷基甲硅烷基）乙炔基和芳基乙炔的偶合反应以制备1-萘基-，1-（1-萘基）-2-苯基- ，和1,2-双（1-萘基）乙炔与各种邻位的取代基，即，对-CH 3，-CH 2 OH，-CO 2 Me和-CH 2 OCH 2 CCCH 3个基团。通过改变芳基卤化物中的卤素原子，溶剂，（三烷基甲硅烷基）乙炔中的烷基和催化剂（Pd（O）vs.）。在具有连接的炔烃单元的1-萘碘化物的情况下，已观察到偶联可与级联的分子内Heck型反应竞争。已经讨论了β-消除氢化钯物种的机理。已经发现带有-CO 2 Me基团的1-萘基溴易于被溶剂进行亲核芳族取代。已经显示，不对称的1-（1-萘基）-2-苯基乙炔衍生物的成功合成关键取决于芳基卤化物/芳基乙炔的组合。
• A Novel Strategy for the Synthesis of Molecules with Helical Chirality. Intramolecular [2 + 2 + 2] Cycloisomerization of Triynes under Cobalt Catalysis
  作者：Irena G. Stará、Ivo Starý、Adrian Kollárovič、Filip Teplý、David Šaman、Miloš Tichý

  DOI：10.1021/jo9801263

  日期：1998.6.1

  A straightforward synthetic approach to a new das's of molecules with helical chirality has been developed involving an intramolecular [2 + 2 + 2] cycloisomerization of triynes under CpCo(CO)(2)/ PPh3 catalysis. The cyclization reaction is promoted by visible light irradiation. Starting from 1,2-diarylacetylenes with two terminal or methyl-substituted tethered acetylene moieties (1a,b,4, 5, and 7), the target products (8a,b, 11, 12, and 14) are obtained in 64-89% yield. The triynes bearing terminal trimethylsilyl groups (Ic, 2, and 3) are less reactive and afford the products (8c, 9a,b, and 10) in 23-71% yield. The ability of the trimethylsilylated derivatives to cycloisomerize strongly depends on the tether length. The cyclized products (8-14) with five, six, and seven ortho-fused rings structurally resemble classical helicenes. Several representatives (8b, 11, 12, and 14) have been resolved into enantiomers by HPLC on a chiral column. Thus, the methodology exhibits a considerable versatility and allows the preparation of a variety of helical objects.