1,2-diphenylethane-1,2-d2-1,2-diol | 36239-19-7

• 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: 1,2-diphenylethane-1,2-d2-1,2-diol
• 英文别名: 1,2-Ethane-1,2-d2-diol, 1,2-diphenyl-；1,2-dideuterio-1,2-diphenylethane-1,2-diol
• CAS: 36239-19-7
• 化学式: C₁₄H₁₄O₂
• 分子量: 216.248
• InChiKey: IHPDTPWNFBQHEB-FLZZRPEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2-diphenylethane-1,2-d2-1,2-diol 在 硝酸铵 、 lead(IV) acetate 、 对甲苯磺酸 作用下， 以 乙醚 、 苯 为溶剂， 反应 19.0h， 生成 2-Deutero-2-phenyl-1,3-dioxolan
  参考文献：
  名称：

  Steinbeck, Karl; Klein, Joachim, Journal of Chemical Research, Miniprint, 1980, # 3, p. 1150 - 1162

  摘要：

  DOI：
• 作为产物：
  描述：

  联苯甲酰 在 硼氘化钠 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以100%的产率得到1,2-diphenylethane-1,2-d2-1,2-diol
  参考文献：
  名称：

  Synthesis of Z- and E-[2,3-2H2] and [2,3-3H2]-1,1-dichloro-2,3- diphenylcyclopropane (2H- and 3H-analog II and its trans isomer)

  摘要：

  合成了标记为2H和3H的Z-和E-1,1-二氯-2,3-二苯基环丙烷（1和2），起始材料为磷酸二钠（NaB2H4）和磷酸三钠（NaB3H4）还原苯基。生成的醇类通过在三甲基磷酸酯中热解其环硫碳酸酯转化为1,2标记的Z-和E-斯蒂尔本。斯蒂尔本与相转移生成的二氯羰基反应，形成目标化合物。二重氘异构体通过分馏结晶分离，产率为60%和48%。每种异构体的几何纯度超过99%，同位素纯度为98%。重氚异构体通过C-18 JPLC分离。以苯二酮为限量试剂的摩尔基放射化学产率为42%和23%，每种的特定活度为88.5 mCi/mmol，放射化学纯度均超过95%。

  DOI：

  10.1002/jlcr.2580360109

文献信息

• Synthesis of Deuterated (<i>E</i>)-Alkene through Xanthate-Mediated Hydrogen–Deuterium Exchange Reactions
  作者：Jiaming Li、Jian Li、Xiaoliang Ji、Runfa He、Yang Liu、Zebin Chen、Yubing Huang、Qiang Liu、Yibiao Li

  DOI：10.1021/acs.orglett.1c02600

  日期：2021.10.1

  Herein we have developed a reversible hydrogen–deuterium exchange reaction of nonactivated olefins. By using EtOCS2K as a mediator, the H/D exchange reaction was realized through repeated addition and elimination reactions, demonstrating reversible H/D exchange between ordinary olefins and deuterated olefins. Using the lowest cost D2O without precious metal catalysts and ligands, a broad spectrum of

  在此，我们开发了非活化烯烃的可逆氢-氘交换反应。以EtOCS 2 K为介体，通过反复加成和消去反应实现H/D交换反应，证明了普通烯烃和氘化烯烃之间的H/D交换是可逆的。在没有贵金属催化剂和配体的情况下使用最低成本的 D 2 O，实现了广泛的官能团兼容性。
• Synthesis of Z- and E-[2,3-2H2] and [2,3-3H2]-1,1-dichloro-2,3- diphenylcyclopropane (2H- and 3H-analog II and its trans isomer)
  作者：Billy W. Day、Sastry S. Jonnalagadda

  DOI：10.1002/jlcr.2580360109

  日期：1995.1

  2H and 3H labeled Z- and E-1,1-dichloro-2,3-diphenylcyclopropane (1 and 2) were synthesized starting from NaB2H4 and NaB3H4 reduction of benzil. The resulting glycols were transformed to the 1,2-labeled Z- and E-stilbenes by thermolysis of their cyclic thionocarbonates in trimethylphosphite. The stilbenes were reacted with phase transfer-generated dichlorocarbene to form the title compounds. The dideuterio isomers were separated by fractional crystallization in yields of 60 and 48%. Each was greater than 99 % geometrically and 98 % isotopically pure. The ditritio isomers were separated by C-18 JPLC. The radiochemical yields, on a molar basis using benzil as the limiting reagent, were 42 % and 23 %, each with specific activity of 88.5 mCi/mmol and radiochemical purity of > 95%.

  合成了标记为2H和3H的Z-和E-1,1-二氯-2,3-二苯基环丙烷（1和2），起始材料为磷酸二钠（NaB2H4）和磷酸三钠（NaB3H4）还原苯基。生成的醇类通过在三甲基磷酸酯中热解其环硫碳酸酯转化为1,2标记的Z-和E-斯蒂尔本。斯蒂尔本与相转移生成的二氯羰基反应，形成目标化合物。二重氘异构体通过分馏结晶分离，产率为60%和48%。每种异构体的几何纯度超过99%，同位素纯度为98%。重氚异构体通过C-18 JPLC分离。以苯二酮为限量试剂的摩尔基放射化学产率为42%和23%，每种的特定活度为88.5 mCi/mmol，放射化学纯度均超过95%。
• Mg(OMe)₂ promoted allylic isomerization of γ-hydroxy-α,β-alkenoic esters to synthesize γ-ketone esters
  作者：Luhao Lai、A-Ni Li、Jiawei Zhou、Yarong Guo、Li Lin、Wei Chen、Rui Wang

  DOI：10.1039/c7ob00131b

  日期：——

  This work concerns the Mg(OMe)2 promoted allylic isomerization of γ-hydroxy-α,β-alkenoic esters with TMEDA as an additive. The isomerization proceeded under mild conditions and afforded γ-keto esters in high yield (up to 96%) within 2 h. Both (Z)- and (E)-γ-hydroxy-α,β-alkenoic esters were tolerated under the reaction conditions. This transformation involves the in situ formation of a dienolate intermediate

  这项工作涉及以TMEDA作为添加剂的Mg（OMe）2促进的γ-羟基-α，β-链烯酸酯的烯丙基异构化。异构化在温和的条件下进行，并在2小时内以高收率（高达96％）提供了γ-酮酯。在反应条件下，（Z）-和（E）-γ-羟基-α，β-链烯酸酯均被耐受。该转化涉及从容易获得的γ-羟基-α，β-链烯酸酯原位形成二烯酸酯中间体。该原位生成的二烯醇酯可以与苯甲醛反应并经历一种实用，有用的串联烯丙基异构化-羟醛反应，得到更多官能的化合物。
• Successive C–C Coupling of Dienes to Vicinally Dioxygenated Hydrocarbons: Ruthenium Catalyzed [4 + 2] Cycloaddition across the Diol, Hydroxycarbonyl, or Dione Oxidation Levels
  作者：Laina M. Geary、Ben W. Glasspoole、Mary M. Kim、Michael J. Krische

  DOI：10.1021/ja400691t

  日期：2013.3.13

  The ruthenium(0) catalyst generated from Ru-3(CO)(12) and tricyclohexylphosphine or BIPHEP promotes successive C-C coupling of dienes to vicinally dioxygenated hydrocarbons across the diol, hydroxyketone, and dione oxidation levels to form products of [4 + 2] cycloaddition. A mechanism involving diene-carbonyl oxidative coupling followed by intramolecular carbonyl addition from the resulting allylruthenium intermediate is postulated.
• Kinetics and mechanism of the oxidation of aromatic aldehydes by hexachloroiridate(IV)
  作者：Kalyan Kali San Gupta、Sanghamitra Dey、Shipra Sen Gupta、Amalendu Banerjee

  DOI：10.1021/jo00200a005

  日期：1984.12