(2S,3R)-2,3-diphenyl-2-prop-2-enyloxirane | 136411-70-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (2S,3R)-2,3-diphenyl-2-prop-2-enyloxirane
• CAS: 136411-70-6；136411-72-8
• 化学式: C₁₇H₁₆O
• 分子量: 236.313
• InChiKey: QUYKULHFNSMIKD-SJORKVTESA-N

物化性质

• 沸点：
  335.0±11.0 °C(Predicted)
• 密度：
  1.072±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.23
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  12.53
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  3-溴丙烯 、 cis-1,2-diphenyloxirane 在 正丁基锂 、 四甲基乙二胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以55%的产率得到(2S,3R)-2,3-diphenyl-2-prop-2-enyloxirane
  参考文献：
  名称：

  Lithiation and Reactions of Stilbene Oxides:  Synthetic Utility

  摘要：

  The lithiation of trans- and cis-stilbene oxides (+/-)-1 and 8 has been investigated. While with 8, lithiation occurred exclusively at the benzylic position, with the trans isomer (+/-)-1, ortho-lithiation competed with alpha-lithiation depending upon the experimental conditions. The configurational stability of the alpha-lithiated cis- and trans-stilbene oxides (+/-)-2 and (+/-)-9, respectively, was proved as well as that of scalemic stilbene oxide (R,R)-2.

  DOI：

  10.1021/ol0485013

文献信息

• The Formation of Cyclic Ethers from Diallyldibutyltin and Halo Ketones Catalyzed by Tetraethylammonium Chloride
  作者：Katsunori Yano、Yukio Hatta、Akio Baba、Haruo Matsuda

  DOI：10.1055/s-1992-26202

  日期：——

  The cyclization reaction of diallyldibutyltin and α- or γ-halo ketones, especially chloro-substituted ketones, effectively proceeds in the presence of a catalytic amount of tetraethylammonium chloride, producing the corresponding 2-allyloxiranes or 2-allyltetrahydrofurans in high yield, respectively. β-Chloro ketones give the corresponding allyl alcohols.

  二烯丙基二丁基锡与α-或γ-卤代酮，尤其是氯代酮的环化反应，在催化量的氯化四乙基铵存在下有效进行，分别高产率地生成相应的2-烯丙基环氧乙烷或2-烯丙基四氢呋喃。β-氯代酮则生成相应的烯丙醇。
• Lithiation and Reactions of Stilbene Oxides:  Synthetic Utility
  作者：Saverio Florio、Varinder Aggarwal、Antonio Salomone

  DOI：10.1021/ol0485013

  日期：2004.11.1

  The lithiation of trans- and cis-stilbene oxides (+/-)-1 and 8 has been investigated. While with 8, lithiation occurred exclusively at the benzylic position, with the trans isomer (+/-)-1, ortho-lithiation competed with alpha-lithiation depending upon the experimental conditions. The configurational stability of the alpha-lithiated cis- and trans-stilbene oxides (+/-)-2 and (+/-)-9, respectively, was proved as well as that of scalemic stilbene oxide (R,R)-2.