dimethyl (2Z)-2-(phenylseleno)but-2-enedioate | 132330-34-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: dimethyl (2Z)-2-(phenylseleno)but-2-enedioate
• 英文别名: dimethyl (Z)-2-phenylselanylbut-2-enedioate
• CAS: 132330-34-8
• 化学式: C₁₂H₁₂O₄Se
• 分子量: 299.185
• InChiKey: LYGMDVGBTYAHHH-NTMALXAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.25
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dimethyl (2Z)-2-(phenylseleno)but-2-enedioate 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 1.17h， 生成 (2S,3S,4S)-4-Methyl-5-oxo-2-phenyl-tetrahydro-furan-3-carboxylic acid methyl ester
  参考文献：
  名称：

  D'Onofrio, Franco, Chemical Communications, 1998, # 2, p. 185 - 186

  摘要：

  DOI：
• 作为产物：
  描述：

  dimethyl (2S,3S)-2-chloro-3-phenylselanylbutanedioate 在 aluminum oxide 作用下， 以 乙醚 为溶剂， 生成 dimethyl (2Z)-2-(phenylseleno)but-2-enedioate
  参考文献：
  名称：

  The binary reagent PhSeClZnCl2: a powerful chloro-phenylselenenylating agent of electrophilic olefins

  摘要：

  The binary reagent PhSeCl-ZnCl2 was found to be powerful for the stereocontrolled conversion of highly electrophilic olefins, such as maleate and fumarate esters, into the corresponding chloro phenylseleno derivatives in very high yields. Other olefins, such as methyl acrylate and methyl vinyl ketone, react virtually instantaneously.

  DOI：

  10.1016/0040-4039(95)00159-a

文献信息

• “On-Water” Michael-Type Addition Reactions Promoted by PhSeZnCl
  作者：Benedetta Battistelli、Testaferri Lorenzo、Marcello Tiecco、Claudio Santi

  DOI：10.1002/ejoc.201100045

  日期：2011.4

  communication we report that our reagent PhSeZnCl can be conveniently used to effect Michael addition like reactions of unsaturated ketones and electron-deficient alkynes, leading to synthetically useful β-seleno derivatives and vinyl selenides, respectively. The reactions are effected at room temperature in THF as well as under "on water" conditions. When the addition occurs on a triple bond, good stereoselectivity

  在这篇通讯中，我们报告说我们的试剂 PhSeZnCl 可以方便地用于影响不饱和酮和缺电子炔烃的迈克尔加成反应，分别导致合成有用的 β-硒代衍生物和乙烯基硒化物。反应在室温下在 THF 中以及在“水上”条件下进行。当加成发生在三键上时，观察到良好的立体选择性，并且反应在水悬浮液中显示出速率加速。
• Ru-Catalyzed and Selenium-Directed Selective Formation of <i>ortho</i>- and Dialkenylated Selanes, Mixed Organoselenoethers, and Isoselenochromenes
  作者：Sangeeta Kumari、Deepak Sharma、Charu Sharma、Lalit Negi、Raj K. Joshi

  DOI：10.1021/acs.orglett.3c04028

  日期：2024.3.8

  Herein, the Ru-catalyzed chemo- and regioselective formation of four novel organoselenium compounds is established. Mono- and dialkenylated selanes were formed by the Se-directed o-C–H activation of benzyl(phenyl)selanes with alkynes. Unprecedented debenzylative/dearylative hydroselenations of alkynes were performed by slightly varying the amount of catalyst and temperature. Catalyst-driven direct formation

  在此，建立了四种新型有机硒化合物的钌催化化学和区域选择性形成。单烯基化和二烯基化的硒烷是通过Se引导的o -C-H与炔烃对苄基（苯基）硒烷进行活化而形成的。通过稍微改变催化剂的量和温度，进行了前所未有的炔烃脱苄基/脱芳基氢化硒化反应。还记录了催化剂驱动的新型异硒色烯的直接形成。总共用各种炔烃和硒烷合成了大量的 45 种新的有机硒化合物。这是同类报告中第一篇涉及在一个反应​​中合成新颖、具有挑战性和不寻常的有机硒化合物的报告。
• Kataoka, Tadashi; Yoshimatsu, Mitsuhiro; Noda, Yoshinori, Journal of the Chemical Society. Perkin transactions I, 1993, # 1, p. 121 - 130
  作者：Kataoka, Tadashi、Yoshimatsu, Mitsuhiro、Noda, Yoshinori、Sato, Takashi、Shimizu, Hiroshi、Hori, Mikio

  DOI：——

  日期：——
• Selenium-directed conjugate addition of amines to dimethyl 2-phenylseleno fumarate : Regio and diastereoselective synthesis of 2-phenylseleno-3-amino succinates
  作者：Marco Bella、Franco D'Onofrio、Roberto Margarita、Luca Parlanti、Giovanni Piancatelli、Alfonso Mangoni

  DOI：10.1016/s0040-4039(97)10046-6

  日期：1997.11

  Dimethyl 2-phenylseleno fumarate 1 acts as a strong Michael acceptor of amines, providing the corresponding 2-phenylseleno-3-amino succinates 2a and 2b in very high yields with complete regio-and good diastereoselectivity. (C) 1997 Elsevier Science Ltd.
• KATAOKA, TADASHI;YOSHIMATSU, MITSUHIRO;SHIMIZU, HIROSHI;HORI, MIKIO, TETRAHEDRON LETT., 31,(1990) N1, C. 5927-5930
  作者：KATAOKA, TADASHI、YOSHIMATSU, MITSUHIRO、SHIMIZU, HIROSHI、HORI, MIKIO

  DOI：——

  日期：——