methyl 6-naphthalen-2-ylhex-2-enoate | 141943-14-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl 6-naphthalen-2-ylhex-2-enoate
• CAS: 141943-14-8
• 化学式: C₁₇H₁₈O₂
• 分子量: 254.329
• InChiKey: TVEUEGDUHCJEQS-UHFFFAOYSA-N

物化性质

• 沸点：
  404.1±24.0 °C(Predicted)
• 密度：
  1.077±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.89
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  在 1,4-环己二烯 、 四丁基氟化铵 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 生成 methyl 6-naphthalen-2-ylhex-2-enoate
  参考文献：
  名称：

  Synthetic studies of the tandem enediyne-mono- and bisradical cyclizations

  摘要：

  The readily synthesized enediynes 12a-j possessing a tethered olefin radical acceptor can participate in a tandem enediyne-radical cyclization to yield dibydrobenzindene derivatives 14a-j. In the present study, the scope of this reaction was expanded to include a wide variety of olefin acceptors. Substitution at both ends of olefin leads to the formation of two diastereomers 14b and 14c in a 3.5:1 ratio when R3 is Me and R2 is CO2Me. The structures of the dihydrobenzindene products 14b and 14c were confirmed by generating a radical from 25 by a tributyltin hydride reaction which undergoes radical cyclization; this radical is similar to the enediyne-generated radical, which also cyclizes. It was shown that, in 14i and 14j, a substituent at R1 slowed the reaction but still resulted in a good to excellent yield of product. A tandem enediyne-6-exo-radical cyclization of 16 was also carried out but did not work as well as its 5-exo counterpart 12a. Finally, an enediyne 33 containing two olefinic tethers was cyclized in a process to form tetracycle 34 where three rings were formed in one synthetic operation.

  DOI：

  10.1021/ja00078a013

文献信息

• The tandem bergman-radical cyclization: a new method for ring annulation
  作者：Janet Wisniewski Grissom、Trevor L. Calkins

  DOI：10.1016/s0040-4039(00)74199-2

  日期：1992.4

  Heading of enediynes 1a, 1b and 2 at 210° C in a sealed tube in the presence of a hydrogen atom source yields naphthalene derivatives 3a, 3b and 4 in yields of 53-72%.

  在氢原子源的存在下，在密封管中于210℃下对苯二炔1a，1b和2的抽头，得到萘衍生物3a，3b和4，产率为53-72％。