1-cyano-2-(5-methyl-2-oxa-4-hexenyl)naphthalene | 183657-20-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-cyano-2-(5-methyl-2-oxa-4-hexenyl)naphthalene
• 英文别名: 2-{[(3-Methylbut-2-en-1-yl)oxy]methyl}naphthalene-1-carbonitrile；2-(3-methylbut-2-enoxymethyl)naphthalene-1-carbonitrile
• CAS: 183657-20-7
• 化学式: C₁₇H₁₇NO
• 分子量: 251.328
• InChiKey: MKVPYOLHOWWJPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-cyano-2-(5-methyl-2-oxa-4-hexenyl)naphthalene 在 L-(+)-酒石酸二乙酯 作用下， 以 环己烷 为溶剂， 反应 6.0h， 生成 11,11-Dimethyl-14-oxatetracyclo[8.5.0.01,12.04,9]pentadeca-2,4,6,8-tetraene-10-carbonitrile
  参考文献：
  名称：

  Asymmetric induction in an intramolecular [2+2] photocycloaddition within chirally modified zeolite supercages

  摘要：

  Photoirradiation of 1-cyano-2-(5-methyl-2-oxa-4-hexenyl)naphthalene, included in NaY zeolites along with chiral inductors, such as diethyl tartrate or phenylalaninol, gives an intrarnolecular [2+2] photocycloadduct with a maximum 15% ee. The degree of enantioselectivity was found to depend on the Si/Al ratio, the nature of the cations in the zeolites, the structure of the chiral inductors, and the molar ratio of substrate and chiral inductors. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.02.012
• 作为产物：
  描述：

  (1R,10R,12R)-11,11-dimethyl-14-oxatetracyclo[8.5.0.01,12.04,9]pentadeca-2,4,6,8-tetraene-10-carbonitrile 以 乙腈 为溶剂， 生成 1-cyano-2-(5-methyl-2-oxa-4-hexenyl)naphthalene
  参考文献：
  名称：

  通过烯烃的分子内[2 + 3]光环加成反应，一步合成苯并四环和苯并五环化合物。

  摘要：

  DOI：

  10.1002/anie.200602553

文献信息

• Site-Selective Intramolecular Photocycloaddition of 2-Alkenyl-Substituted 1-Cyanonaphthalenes Depending on Additives, Solvents, and Substituents
  作者：Kazuhiko Mizuno、Yasuharu Yoshimi、Shin-ichi Konishi、Hajime Maeda

  DOI：10.1055/s-2001-15068

  日期：——

  Irradiation of 2,3-dimethylbut-2-enyl 1-cyano-2-naphthylmethyl ether in the presence of Eu(hfc)3 in benzene site-selectively afforded the (2π + 2π) intramolecular photocycloadduct at the 1,2-position on the naphthalene ring. On the other hand, allyl 1-cyano-2-naphthylmethyl ether in the presence of Mg(ClO4)2 in acetonitrile gave the photocycloadduct at the 3,4-position as a sole product.

  在苯中，2,3-二甲基-2-丁烯基1-氰基-2-萘甲基醚在Eu(hfc)3的存在下，择位选择性地生成了萘环1,2-位的(2π + 2π)分子内光环加成产物。另一方面，丙烯基1-氰基-2-萘甲基醚在醋腈中加入Mg(ClO4)2，仅生成3,4-位的光环加成产物。
• Intramolecular Photocycloaddition of 2-(2-Alkenyloxymethyl)naphthalene-1-carbonitriles Using Glass-Made Microreactors
  作者：Hirofumi Mukae、Hajime Maeda、Satoshi Nashihara、Kazuhiko Mizuno

  DOI：10.1246/bcsj.80.1157

  日期：2007.6.15

  Intramolecular [2+2] and [2+3] photocycloadditions of 2-(2-alkenyloxymethyl)naphthalene-1-carbonitriles and their photocycloreversion using glass-made microreactors were investigated in comparison with photoreactions under conventional batch conditions. Both the efficiency and regioselectivity were improved by use of glass-made microreactors. These results can be explained by thorough absorption of light and outflow of primary product from the reaction system.

  研究了2-(2-烯基氧甲基)萘-1-氰基的分子内[2+2]和[2+3]光环加成及其在玻璃微反应器中的光环逆反应，并与传统批量反应条件下的光反应进行了比较。使用玻璃微反应器提高了反应的效率和区域选择性。这些结果可以通过对光的充分吸收以及主要产物从反应系统中的流出进行解释。
• Enhanced Efficiency and Regioselectivity of Intramolecular (2π + 2π) Photocycloaddition of 1-Cyanonaphthalene Derivative Using Microreactors
  作者：Hajime Maeda、Hirofumi Mukae、Kazuhiko Mizuno

  DOI：10.1246/cl.2005.66

  日期：2005.1

  The intramolecular photocycloaddition of a 1-cyanonaphthalene derivative in microreactors made of poly(dimethylsiloxane) (PDMS) was examined. By using the microreactors and flow system, both the efficiency and regioselectivity increased compared with those under batch conditions.

  在聚二甲基硅氧烷（PDMS）微反应器中考察了一种1-氰基萘衍生物的分子内光环加成反应。通过使用微反应器和流动系统，与批次条件相比，反应的效率和区域选择性都有所提高。
• One-Step Synthesis of Benzotetra- and Benzopentacyclic Compounds through Intramolecular [2+3] Photocycloaddition of Alkenes to Naphthalene
  作者：Hirofumi Mukae、Hajime Maeda、Kazuhiko Mizuno

  DOI：10.1002/anie.200602553

  日期：2006.10.6
• Asymmetric induction in an intramolecular [2+2] photocycloaddition within chirally modified zeolite supercages
  作者：Hajime Maeda、Takahiro Okumura、Yasuharu Yoshimi、Kazuhiko Mizuno

  DOI：10.1016/j.tetasy.2009.02.012

  日期：2009.2

  Photoirradiation of 1-cyano-2-(5-methyl-2-oxa-4-hexenyl)naphthalene, included in NaY zeolites along with chiral inductors, such as diethyl tartrate or phenylalaninol, gives an intrarnolecular [2+2] photocycloadduct with a maximum 15% ee. The degree of enantioselectivity was found to depend on the Si/Al ratio, the nature of the cations in the zeolites, the structure of the chiral inductors, and the molar ratio of substrate and chiral inductors. (C) 2009 Elsevier Ltd. All rights reserved.