3-methylseleno-2-methyl-selenomethyl-1-propene | 188245-07-0

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 3-methylseleno-2-methyl-selenomethyl-1-propene
• 英文别名: 4-methylene-2,6-diselenaheptane；3-Methylselanyl-2-(methylselanylmethyl)prop-1-ene
• CAS: 188245-07-0
• 化学式: C₆H₁₂Se₂
• 分子量: 242.081
• InChiKey: UJPLOKDWSXKTSU-UHFFFAOYSA-N

物化性质

• 沸点：
  255.7±40.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.88
• 重原子数：
  8
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  3-methylseleno-2-methyl-selenomethyl-1-propene 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 3-lithio-2-(methylselenomethyl)propene
  参考文献：
  名称：

  3-甲基硒代-2- [甲基硒代甲基]-丙烯的有价值的亚甲基甲烷和三亚甲基甲烷二阴离子的前体

  摘要：

  3-甲基硒基-2- [甲基硒基甲基]-丙烯被证明是3-硫基-2- [甲基硒基甲基]-丙烯和3-硫基-2- [硫代甲基]-丙烯的有价值的前体。这些已与各种亲电试剂反应，并已成功地转化为官能化的环醚。

  DOI：

  10.1016/s0040-4039(96)02385-4
• 作为产物：
  描述：

  3-氯-2-氯甲基丙烯 、 二甲基二硒醚 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以95%的产率得到3-methylseleno-2-methyl-selenomethyl-1-propene
  参考文献：
  名称：

  不对称双金属异丁烯衍生物的方便和多功能制备

  摘要：

  合成有用的不对称双甲硅烷基或甲硅烷基甲硅烷基异丁烯衍生物可方便地从硒异丁烯 5 制备，硒异丁烯 5 是异丁烯二价阴离子的通用等价物。用正丁基锂和所需的氯硅烷或氯锡烷对该硒化化合物进行顺序处理，可有效地生成相应的官能化异丁烯。

  DOI：

  10.1055/s-2006-948188

文献信息

• Preparation and Synthetic Utility of 2-Methylselenomethyl Allyl Methyl Selenide. A Valuable Precursor to 2-Silylmethylallyllithiums
  作者：Alain Krief

  DOI：10.1055/s-1998-1915

  日期：1998.11

  3-Lithio-2-[silylmethyl]propenes, easily prepared from 3-methylseleno-2-[silylmethyl]propenes by the cleavage of the C-Se bond, are useful intermediates for the preparation of a variety of functionalised allylsilanes. These allylsilanes are interesting building blocks, used for example, as annelating agents in the efficient synthesis of spiroketals by the Intramolecular Silyl-Modified Sakurai (ISMS)

  3-Lithio-2-[silylmethyl]propenes 很容易从 3-methylseleno-2-[silylmethyl]propenes 通过 C-Se 键的断裂制备，是制备各种功能化烯丙基硅烷的有用中间体。这些烯丙基硅烷是有趣的结构单元，例如用作通过分子内甲硅烷基改性 Sakurai (ISMS) 环化有效合成螺缩酮的退火剂。本文中描述的方法还提供了获得一系列杂取代甲基硒丙烯的便利途径，这些是一系列有用的杂取代烯丙基锂试剂的有价值的前体。最后，报道了从容易获得的 3-甲基硒基-2-[甲基硒基甲基]丙烯一步制备官能化烯丙基硅烷的方法。
• Synthesis of Spiro-bisperoxyketals
  作者：Prasanta Ghorai、Patrick H. Dussault、Chunhua Hu

  DOI：10.1021/ol800657m

  日期：2008.6.1

  Syntheses of spirocyclic bis-1,2-dioxolanes, bis-1,2-dioxanes, and bis-1,2-dioxepanes are achieved through intramolecular ketalizations of hydroperoxy ketones or intramolecular alkylations of gern-dihydroperoxides. The spiroperoxides have excellent thermal and chemical stability, and several display promising activity against A falciparum.
• Stereoselective synthesis and molecular modeling of chiral cyclopentanes
  作者：Raid J. Abdel-Jalil、Thomas Steinbrecher、Thuraya Al-Harthy、Ahmed Mahal、Osama K. Abou-Zied、Wolfgang Voelter

  DOI：10.1016/j.carres.2015.07.012

  日期：2015.10

  The reaction of 3-methyseleno-2-methylselenomethyl-propene with benzyl 2,3-anhydro-4-O-triflyl-beta-L-ribopyranoside provides a major convenient enantiomeric product of 1-methylene-(benzyl3, 4-dideoxy-alpha-D-arabinopyranoso)-[3,4-c]-cyclopentane, with benzyl-2,3-anhydro-4-deoxy-4-C-(2-methyl- propen-3-yl)-alpha-D-lyxopyranoside as a minor product. While the reaction of 3-methyseleno-2-[methylselenomethyl]-propene with benzyl 2,3-anhydro-4-O-triflyl-alpha-D-ribopyranoside produces a good yield of benzyl-2,3-anhydro-4-deoxy-4-C-(2-methylpropen-3-yl)-alpha-D-lyxo-pyranoside. Molecular modeling and molecular dynamics simulations indicate that the intermediate in the reaction of the beta-L sugar frequently occupies an optimal conformation that leads to the formation of cyclopentane, while the intermediate in the reaction of the alpha-D sugar has a very small probability. The results point to the dominant role of the beta-L sugar intermediate in controlling the cyclopentane formation. (C) 2015 Elsevier Ltd. All rights reserved.
• 3-Methylseleno-2-[methylselenomethyl]-propene valuable precursor of trimethylenemethane and trimethylenemethane dianion
  作者：Alain Krief、Willy Dumont

  DOI：10.1016/s0040-4039(96)02385-4

  日期：1997.1

  3-Methylseleno-2-[methylselenomethyl]-propene proved to be a valuable precursor of 3-lithio-2-[methylselenomethyl]-propene and 3-lithio-2-[lithiomethyl]-propene. These have been reacted with various electrophiles and have in turn be successfully transformed into functionalized cyclic ethers.

  3-甲基硒基-2- [甲基硒基甲基]-丙烯被证明是3-硫基-2- [甲基硒基甲基]-丙烯和3-硫基-2- [硫代甲基]-丙烯的有价值的前体。这些已与各种亲电试剂反应，并已成功地转化为官能化的环醚。
• A Convenient and Versatile Preparation of Unsymmetrical Bis-metallic ­Isobutene Derivatives
  作者：Bernard Leroy、Benoît Driesschaert

  DOI：10.1055/s-2006-948188

  日期：2006.8

  Synthetically useful unsymmetrical bis-silyl or silylstannyl isobutene derivatives are conveniently prepared from selenoisobutene 5, a versatile equivalent of the isobutene dianion. Sequential treatment of this selenated compound with n-butyl-lithium and the required chlorosilanes or chlorostannanes leads efficiently to the corresponding functionalized isobutenes.

  合成有用的不对称双甲硅烷基或甲硅烷基甲硅烷基异丁烯衍生物可方便地从硒异丁烯 5 制备，硒异丁烯 5 是异丁烯二价阴离子的通用等价物。用正丁基锂和所需的氯硅烷或氯锡烷对该硒化化合物进行顺序处理，可有效地生成相应的官能化异丁烯。