1-phenylselanylbutan-2-one | 109297-37-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-phenylselanylbutan-2-one
• 英文别名: 1-phenylselenobutan-2-one；1-phenylselenobutanone；1-(Phenylselanyl)butan-2-one
• CAS: 109297-37-2
• 化学式: C₁₀H₁₂OSe
• 分子量: 227.165
• InChiKey: BBKJMNVOQLWNCG-UHFFFAOYSA-N

物化性质

• 沸点：
  160 °C(Press: 0.4 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  1.41
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(苯硒基)邻苯二甲酰亚胺 、 1-phenylselanylbutan-2-one 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以61%的产率得到1,1-Bis-phenylselanyl-butan-2-one
  参考文献：
  名称：

  Preparation of α,α-bis(phenylseleno)ketones

  摘要：

  alpha,alpha-Bis(phenylseleno)ketones have been synthesized by phenylselenenylation of enolates derived from alpha-phenylseleno ketones. Depending on the structure of the ketones, three experimental procedures were adopted.

  DOI：

  10.1016/0040-4039(95)01290-x
• 作为产物：
  描述：

  苯硒酚 在 磺酰氯 、 水 、 硫脲 作用下， 以 氯仿 、 Petroleum ether 为溶剂， 反应 8.5h， 生成 1-phenylselanylbutan-2-one
  参考文献：
  名称：

  Use of Phenylselenium Trichloride For Simple and Rapid Preparation of α-Phenylselanyl Aldehydes and Ketones

  摘要：

  α-苯硒基醛通过PhSeCl3与相应醛在乙腈中反应大规模制备，无需分离二氯加成中间体。该方法已应用于由烷基芳基酮、对称脂肪酮和烷基异丙基酮衍生的α-苯硒基酮，并同样制备了顺-4-叔丁基-2-苯硒基环己酮。

  DOI：

  10.1055/s-1997-1509

文献信息

• Stereoselective aldol reaction of α-seleno carbonyl compounds: preparation of (Z)-α,β-unsaturated carbonyl compounds
  作者：Shuichi Nakamura、Toshinobu Hayakawa、Tatsuya Nishi、Yoshihiko Watanabe、Takeshi Toru

  DOI：10.1016/s0040-4020(01)00606-8

  日期：2001.7

  titanium enolates of α-seleno esters in the presence of Ph3P or Ph3PO gave the products with high stereoselectivity favoring the syn isomers. Reaction of α-seleno ketones with TiCl4 in the presence of 2 equiv. of Et3N, and subsequently with aldehydes, gave the aldol products with high syn selectivity. The stereoselectivity in the aldol reaction of 3-pentanone also increased by using an excess amount of Et3N

  α-硒基酯的烯醇化物的钛的pH值的存在醛醇缩合反应3 P或博士3 PO，得到的产品具有高的立体选择性有利于顺式异构体。在2当量存在下，α-硒代酮与TiCl 4的反应。Et 3 N，然后与醛混合，得到具有高顺式选择性的醛醇产物。通过使用过量的Et 3 N ，3-戊酮的醛醇缩合反应中的立体选择性也增加了。这样从α-硒代羰基化合物获得的醛醇产物可以立体定向转化为（Z）-α，β-不饱和羰基化合物用吡啶处理。（Z）-亚烷基环戊酮仅通过在黑暗中用Et 3 N处理顺-醛醇产物而形成。
• Phenyl Tributylstannyl Selenide as a Promising Reagent for Introducion of the Phenylseleno Group
  作者：Yutaka Nishiyama、Hiroaki Kawamatsu、Saori Funato、Keiji Tokunaga、Noboru Sonoda

  DOI：10.1021/jo026894i

  日期：2003.5.1

  A new synthetic method of organoselenium compounds has been developed. When phenyl tributylstannyl selenide (PhSeSnBu3) was allowed to react with acyl or aroyl chlorides in the presence of a catalytic amount of a palladium complex such as Pd(PPh3)(4), Se-phenyl selenol esters were obtained in moderate to good yields. Similarly, the palladium complex catalyzed the reaction of PhSeSnBu3 with alpha-halo carbonyl compounds to afford the corresponding alpha-phenyseleno carbonyl compounds in moderate yields.
• Regiodefined synthesis of α-bromo, α-phenylthio, and α-phenylseleno ketones by means of specific substitution of the trimethylsilyl group in α-trimethylsilyl ketones
  作者：Isamu Matsuda、Susumu Sato

  DOI：10.1016/0022-328x(86)80349-7

  日期：1986.10
• MATSUDA ISAMU; SATO SUSUMU, J. ORGANOMET. CHEM., 314,(1986) N 1-2, 47-52
  作者：MATSUDA ISAMU、 SATO SUSUMU

  DOI：——

  日期：——
• Use of Phenylselenium Trichloride For Simple and Rapid Preparation of α-Phenylselanyl Aldehydes and Ketones
  作者：Didier Houllemare、Sylvain Ponthieux、Francis Outurquin、Claude Paulmier

  DOI：10.1055/s-1997-1509

  日期：1997.1

  α-Phenylselanyl aldehydes are prepared on a large scale by reaction of PhSeCl3 with the corresponding aldehydes in acetonitrile without isolation of the intermediate dichloro adducts. This method has been applied to α-phenylselanyl ketones derived from alkyl aryl ketones, symmetrical aliphatic ketones and alkyl isopropyl ketones. cis-4-tert-Butyl-2-phenylselanylcyclohexanone was also prepared in the same way.

  α-苯硒基醛通过PhSeCl3与相应醛在乙腈中反应大规模制备，无需分离二氯加成中间体。该方法已应用于由烷基芳基酮、对称脂肪酮和烷基异丙基酮衍生的α-苯硒基酮，并同样制备了顺-4-叔丁基-2-苯硒基环己酮。