(4R)-2-(ethylenedithio-tetrathiafulvalenyl)-4-isopropyl-2-oxazoline | 869796-30-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: (4R)-2-(ethylenedithio-tetrathiafulvalenyl)-4-isopropyl-2-oxazoline
• 英文别名: (4R)-2-[2-(5,6-dihydro-[1,3]dithiolo[4,5-b][1,4]dithiin-2-ylidene)-1,3-dithiol-4-yl]-4-propan-2-yl-4,5-dihydro-1,3-oxazole
• CAS: 869796-30-5
• 化学式: C₁₄H₁₅NOS₆
• 分子量: 405.675
• InChiKey: RBHQRFJLCOPIMM-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  173
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (4R)-2-(ethylenedithio-tetrathiafulvalenyl)-4-isopropyl-2-oxazoline 、 二苯基氯化膦 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以36%的产率得到(R)-2-[2-(5,6-Dihydro-[1,3]dithiolo[4,5-b][1,4]dithiin-2-ylidene)-5-diphenylphosphanyl-[1,3]dithiol-4-yl]-4-isopropyl-4,5-dihydro-oxazole
  参考文献：
  名称：

  基于手性四硫富瓦烯的膦基和硫代甲基-恶唑啉配体。钯催化不对称烯丙基烷基化反应的评价

  摘要：

  合成了基于乙二硫基四硫富瓦烯（EDT-TTF）的具有外消旋或光学纯恶唑啉的新手性氧化还原活性配体。这些助剂在TTF单元上具有附加的功能，即硫代甲基残基或二苯基膦基部分。所有配体均已在不对称的烯丙基取代中进行了测试。达到的对映选择性为85％ee。

  DOI：

  10.1016/j.tet.2006.09.088
• 作为产物：
  描述：

  ethylenedithiotetrathiafulvalene acid chloride 在 甲基磺酰氯 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 (4R)-2-(ethylenedithio-tetrathiafulvalenyl)-4-isopropyl-2-oxazoline
  参考文献：
  名称：

  Tetrathiafulvalene-hydroxyamides and -oxazolines: hydrogen bonding, chirality, and a radical cation salt

  摘要：

  Racemic and enantiopure ethylenedithio-tetrathiafulvalene (EDT-TTF) derivatives featuring beta-hydroxyamide or oxazoline (OX) groups bearing methyl or isopropyl substituents have been synthesized starting from the corresponding amino alcohols. Crystal structure analysis shows in the case of the racemic methyl-beta-hydroxyamide donor the development of a unique hydrogen bond network, characterized by short C=O center dot center dot center dot H-O and N-H center dot center dot center dot O-H intermolecular distances. The enantiopure (S)-EDT-TTF-methyl-OX crystallizes in the monoclinic non-centrosymmetric space group P2(1), whereas the isopropyl counterparts, (R)-and (S)-EDT-TTF-isopropyl-OX, crystallize in the orthorhombic non-centrosymmetric space group P2(1)2(1)2(1). All of them adopt a s-trans conformation in which TTF and oxazoline units are coplanar. Electrocrystallization experiments with the racemic EDT-TTF-methyl-OX, in the presence of (nBu(4))(2)Mo6Cl14 as supporting electrolyte, afford a radical cation salt, formulated as [(+/-)-EDT-TTF-methyl-OX](2)Mo6Cl14, in which the donors associate in strong dimers, which further stack along the b direction to form quasi-homochiral helix-like ribbons. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.08.104

文献信息

• Chiral tetrathiafulvalene based phosphine- and thiomethyl-oxazoline ligands. Evaluation in palladium catalysed asymmetric allylic alkylation
  作者：Céline Réthoré、Isabelle Suisse、Francine Agbossou-Niedercorn、Eva Guillamón、Rosa Llusar、Marc Fourmigué、Narcis Avarvari

  DOI：10.1016/j.tet.2006.09.088

  日期：2006.12

  New chiral redox active ligands based on ethylenedithio-tetrathiafulvalene (EDT-TTF) bearing racemic or optically pure oxazolines have been synthesised. These auxiliaries possess an additional functionality on the TTF unit, namely a thiomethyl residue or a diphenylphosphino moiety. All ligands have been tested in asymmetric allylic substitutions. The enantioselectivity reached is 85% ee.

  合成了基于乙二硫基四硫富瓦烯（EDT-TTF）的具有外消旋或光学纯恶唑啉的新手性氧化还原活性配体。这些助剂在TTF单元上具有附加的功能，即硫代甲基残基或二苯基膦基部分。所有配体均已在不对称的烯丙基取代中进行了测试。达到的对映选择性为85％ee。
• Tetrathiafulvalene-hydroxyamides and -oxazolines: hydrogen bonding, chirality, and a radical cation salt
  作者：Céline Réthoré、Marc Fourmigué、Narcis Avarvari

  DOI：10.1016/j.tet.2005.08.104

  日期：2005.11

  Racemic and enantiopure ethylenedithio-tetrathiafulvalene (EDT-TTF) derivatives featuring beta-hydroxyamide or oxazoline (OX) groups bearing methyl or isopropyl substituents have been synthesized starting from the corresponding amino alcohols. Crystal structure analysis shows in the case of the racemic methyl-beta-hydroxyamide donor the development of a unique hydrogen bond network, characterized by short C=O center dot center dot center dot H-O and N-H center dot center dot center dot O-H intermolecular distances. The enantiopure (S)-EDT-TTF-methyl-OX crystallizes in the monoclinic non-centrosymmetric space group P2(1), whereas the isopropyl counterparts, (R)-and (S)-EDT-TTF-isopropyl-OX, crystallize in the orthorhombic non-centrosymmetric space group P2(1)2(1)2(1). All of them adopt a s-trans conformation in which TTF and oxazoline units are coplanar. Electrocrystallization experiments with the racemic EDT-TTF-methyl-OX, in the presence of (nBu(4))(2)Mo6Cl14 as supporting electrolyte, afford a radical cation salt, formulated as [(+/-)-EDT-TTF-methyl-OX](2)Mo6Cl14, in which the donors associate in strong dimers, which further stack along the b direction to form quasi-homochiral helix-like ribbons. (c) 2005 Elsevier Ltd. All rights reserved.