3',6'-dihydro-4',5'-dimethylspiro<9H-fluorene-9,2'-<2'H>selenopyran> | 117184-21-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 3',6'-dihydro-4',5'-dimethylspiro<9H-fluorene-9,2'-<2'H>selenopyran>
• 英文别名: 3',6'-dihydro-4',5'-dimethylspiro(9H-fluorene-9,2'-[2'H]selenopyran)；3,4-Dimethylspiro[2,5-dihydroselenopyran-6,9'-fluorene]
• CAS: 117184-21-1
• 化学式: C₁₉H₁₈Se
• 分子量: 325.312
• InChiKey: OMHVZMZGSARUCE-UHFFFAOYSA-N

物化性质

• 沸点：
  428.4±45.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.77
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  9-溴芴 在 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 7.0h， 生成 3',6'-dihydro-4',5'-dimethylspiro<9H-fluorene-9,2'-<2'H>selenopyran>
  参考文献：
  名称：

  Preparation and cycloaddition reactions of selenoketones

  摘要：

  DOI：

  10.1021/ja00234a016

文献信息

• An Efficient Synthesis of Selenocarbonyl Compounds by the Treatment of Carbonyl Compounds with Bis[1,5-cyclooctanediylboryl] Selenide
  作者：Kazuaki Shimada、Norikazu Jin、Manabu Fujimura、Yumi Nagano、Eiichi Kudoh、Yuji Takikawa

  DOI：10.1246/cl.1992.1843

  日期：1992.9

  An efficient synthesis of selenoaldehydes, selenoketones, and selenoamides was achieved by the treatment of carbonyl compounds with bis[1,5-cyclooctanediylboryl] selenide.

  通过使用双[1,5-环辛二基硼烷]硒化物处理羰基化合物，实现了硒醛、硒酮和硒酰胺的高效合成。
• Efficient Synthesis of Selenocarbonyl Compounds by Treating Carbonyl Compounds with Bis(1,5-cyclooctanediylboryl) Selenide
  作者：Kazuaki Shimada、Norikazu Jin、Michiko Kawaguchi、Kumiko Dobashi、Yumi Nagano、Manabu Fujimura、Eiichi Kudoh、Tomonari Kai、Noboru Saito、Jun-ichi Masuda、Masaki Iwaya、Hiroyuki Fujisawa、Shigenobu Aoyagi、Yuji Takikawa

  DOI：10.1246/bcsj.70.197

  日期：1997.1

  Selenoaldehydes and selenoketones were generated in situ, by treating aldehydes or ketones, respectively, with bis(1,5-cyclooctanediylboryl) selenide; the resulting selenocarbonyl compounds were trapped with 2,3-dimethyl-1,3-butadiene to give the corresponding [4+2] cycloadducts. The treatment of amides, an ester, and ketones possessing bulky substituents with the reagent also afforded the corresponding selenoamides, a selenoester, and sterically protected selones, respectively, in modest yields. On the other hand, a similar treatment of cinnamaldehyde with the reagent gave the 2,3-dihydroselenophene derivative, which originated from a [4+2]-type self-dimerization of in situ generated 3-phenyl-2-propeneselenal.

  在原位生成硒醛和硒酮，通过将醛或酮与双(1,5-环辛烷二基)硒化物处理；由此得到的硒羰基化合物与2,3-二甲基-1,3-丁二烯反应，形成相应的[4+2]环加成物。将具有体积较大取代基的酰胺、酯和酮与该试剂处理，亦分别得到相应的硒酰胺、硒酯和体积保护的硒酮，产率适中。另一方面，将肉桂醛与该试剂处理，得到2,3-二氢硒苯衍生物，这源于原位生成的3-苯基-2-丙烯硒醛的[4+2]型自聚合反应。
• Preparation of cycloaddition chemistry of thio- and selenocarbonyls derived from reaction of elemental sulfur and selenium with stabilized α-halo anions
  作者：Matthew M. Abelman

  DOI：10.1016/0040-4039(91)80114-l

  日期：1991.12

  Reaction of diethyl chloromalonate with Cs2CO3 in the presence of elemental S8 or Sen generates the corresponding diethyl thioxo- or selenoxomalonates which are subsequently trapped in situ with various 1,3-dienes. Similarly, the chalcogen carbonyls can be prepared from other halogenated using DBU as the base and effectively trapped in Diels-Alder fashion with 2,3-dimethyl-1,3-butadiene (Table 2).

  氯丙二酸二乙酯与Cs 2 CO 3在元素S 8或Se n的存在下反应，生成相应的二乙基硫代肟酸或亚硒酸丙二酸酯，随后将其与各种1,3-二烯原位捕获。同样，硫族化合物羰基化合物可以用DBU作为碱从其他卤代物中制备，并以Diels-Alder方式有效地被2,3-二甲基-1,3-丁二烯捕获（表2）。
• MEINKE, PETER T.;KRAFFT, GRANT A., J. AMER. CHEM. SOC., 110,(1988) N6, C. 8679-8685
  作者：MEINKE, PETER T.、KRAFFT, GRANT A.

  DOI：——

  日期：——
• Preparation and cycloaddition reactions of selenoketones
  作者：Peter T. Meinke、Grant A. Krafft

  DOI：10.1021/ja00234a016

  日期：1988.12