diethyl 1,3-dithiol-2-yl-phosphonate | 122301-25-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: diethyl 1,3-dithiol-2-yl-phosphonate
• 英文别名: Diethyl 2H-1,3-dithiol-2-ylphosphonate；2-diethoxyphosphoryl-1,3-dithiole
• CAS: 122301-25-1
• 化学式: C₇H₁₃O₃PS₂
• 分子量: 240.284
• InChiKey: PJUDYYPATRKRHD-UHFFFAOYSA-N

物化性质

• 沸点：
  359.3±42.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  86.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl 1,3-dithiol-2-yl-phosphonate 在 potassium tert-butylate 、 苯甲酸 作用下， 以 四氢呋喃 为溶剂， 生成 [(4Z,9Z)-7-(Diethoxy-phosphoryl)-[1,3,6,8]tetrathiecin-2-yl]-phosphonic acid diethyl ester
  参考文献：
  名称：

  Synthesis of unsymmetrically substituted TTF derivatives via the “phosphonate way”. Limitations due to the instability of some metalated 1,3-dithiol-2-yl-phosphonates

  摘要：

  The poor results in the syntheses of unsymmetrically substituted TTF derivatives carried out with mono or unsubstituted diethyl 1,3-dithiol-2-yl-phosphonates is here explained by the existence of an equilibrium between the cyclic and open forms of their corresponding carbanionic salt, with possible dimerisation of the open form. The monomeric cyclic form can react with a high reactive iminium salt, affording then the corresponding TTF derivative in moderate yield. (C) 1999 Published by Elsevier Science Ltd. Ail rights reserved.

  DOI：

  10.1016/s0040-4039(99)01466-5
• 作为产物：
  描述：

  三硫代碳酸亚乙烯酯 、 亚磷酸三乙酯 反应 6.0h， 以14%的产率得到diethyl 1,3-dithiol-2-yl-phosphonate
  参考文献：
  名称：

  A One-Step Synthesis of 1,3-Dithiol-2-ylphosphonate Esters from 1,3-Dithiole-2-thiones

  摘要：

  只需在高稀释度的三烷基亚磷酸酯存在下加热，就能从相应的 1,3-二硫杂环戊烯-2-硫酮 1 一步制备出有用的 1,3-二硫杂环戊烯-2-基膦酸酯 3，而且收率很高（高达 75%）。

  DOI：

  10.1055/s-1994-25437

文献信息

• Efficient electron-donating groups for nonlinear optical applictions
  申请人：ENICHEM S.p.A.

  公开号：EP0602654A1

  公开（公告）日：1994-06-22

  Nonlinear optical materials having structures with delocalized resonance configurations corresponding to: or: wherein A is a first electron accepting group, R is pi-conjugated non-centrosymmetric organic moiety; R₄ and R₅ are independently selected from hydrogen, alkyl moieties and functionalized alkyl moieties; E, F, G and H are members of a saturated or unsaturated five- to ten-membered cyclic ring or two-ring systems having five- to ten-membered rings that are electron donating in nature and E, F, G and H are independently selected from -CH-, -CH₂-, O, S, N, Se, Te, and -NR₂-, wherein R₂ is selected from hydrogen, alkyl moieties and functionalized alkyl moieties; and R₁ is selected from alkyl moieties and functionalized alkyl moieties. Polymers blended with or having the disclosed nonlinear optical materials as pendant side chains and exhibiting second order nonlinear optical properties are also disclosed.

  具有结构具有与以下相对应的离域共振构型的非线性光学材料：其中A是第一个电子受体基团，R是π共轭非中心对称有机基团；R₄和R₅分别选自氢、烷基基团和官能化烷基基团；E、F、G和H是饱和或不饱和的五至十元环或具有电子给予性质的五至十元环的两环系统的成员，并且E、F、G和H分别选自-CH-、-CH₂-、O、S、N、Se、Te和-NR₂-，其中R₂选自氢、烷基基团和官能化烷基基团；R₁选自烷基基团和官能化烷基基团。还公开了与所述非线性光学材料混合或具有其作为挂链侧链的聚合物，展现二阶非线性光学性质。
• Synthesis, Structure, and Electrochemical Properties of Extended Tetrathiafulvalene Dimers Linked by Flexible Butylene Chain
  作者：Yuji Kawasaki、Ryo Sakakibara、Masahiro Fujisaki、Masaki Yamashita、Aya Yoshimura、Takashi Shirahata、Masaru Yao、Yohji Misaki

  DOI：10.1246/bcsj.20200357

  日期：2021.3.15

  Tetrathiafulvalene derivatives bridged by butylene unit were successfully synthesized. X-ray structure analysis of the dimeric EBDT 1 revealed that C–C bonds have staggered arrangement and all substituents are arranged anti to each other in the butylene bridge. Cyclic voltammograms of the molecules 1 and the fused TTF analog 2 consisted of two-pairs of two-electron and four pairs of two-electron redox

  成功合成了由丁烯单元桥接的四硫富瓦烯衍生物。对二聚体EBDT 1的X射线结构分析表明，CC键具有交错排列，并且所有取代基在丁烯桥中彼此反位。分子1和融合的TTF类似物2的循环伏安图分别由两对两电子氧化还原波和四对两电子氧化还原波组成。X射线结构分析和未取代-1（1Aa）的两性盐的重叠积分的计算表明，EBDT单元堆叠时具有很强的二聚作用。使用分子2（2Ce）作为正极材料的初始放电容量为179 mAh g -1，初始能量密度为600 mWh g -1，平均电压为3.35 V.
• Optimization of thermal stability and second-order nonlinear optical properties of thiophene derived chromophores
  作者：Alex K-Y. Jen、Varanasi Pushkara Rao、Kevin J. Drost、King Y. Wong、Michael P. Cava

  DOI：10.1039/c39940002057

  日期：——

  Based on the ‘unconventional’ dithiolydinemethyl type donors and tricyanovinyl acceptor; a new series of highly efficient (βµ= 940–2400 × 10–48 esu) and thermally stable (275–315 °C) thiophene derived nonlinear optical chromophores have been developed.

  基于“非常规”二硫代甲基型供体和三氰基乙烯基受体；开发了一系列新的高效（βμ= 940–2400 × 10–48 esu）和热稳定（275–315 °C）噻吩衍生的非线性光学发色团。
• Dendralene-Type TTF Vinylogs Containing a 1,3-Diselenole Ring
  作者：Ramiya R. Amaresh、Dezhong Liu、Tatyana Konovalova、M. V. Lakshmikantham、Michael P. Cava、Lowell D. Kispert

  DOI：10.1021/jo010663e

  日期：2001.11.1

  2-Diformylmethylene-1,3-diselenole was prepared and condensed with dithiolium phoshonium bromides and dithiolium phosphonates in the presence of base to give dendralene-type vinylogs of TTF bearing a 1,3-diselenole moiety. The electrochemistry of these dendrimers was studied. SEEPR measurements were also carried out. Calculations were carried out on the radical cations and correlated with the EPR values

  制备2-二甲酰基亚甲基-1，3-二硒代苯并与二硫鎓溴化膦和二硫代膦酸酯在碱存在下缩合，得到带有1，3-二硒代烯部分的TTF的树枝状烯丙基乙烯基。研究了这些树枝状大分子的电化学。还进行了SEEPR测量。对自由基阳离子进行了计算并与EPR值相关。
• Synthesis, electrochemical and photochromic behaviour of a series of (1,4-dithiafulven-6-yl)substituted 3H-naphtho[2,1-b]pyran derivatives
  作者：Aude-Emmanuelle Navarro、Fabrice Moggia、Corinne Moustrou、Arnault Heynderickx、Frédéric Fages、Philippe Leriche、Hugues Brisset

  DOI：10.1016/j.tet.2004.10.084

  日期：2005.1

  The synthesis and electrochemical and photochromic properties of new 3,3-diphenyl-8-(1,4-dithiafulven-6-yl)-[3H]-naphtho[2,1-b]pyran derivatives containing differently substituted dithiafulvenyl units are described. An example of electrochemical dimerization is shown which gives access to electroactive bichromophoric systems. Such systems could allow the study of the interplay of photochromic and electrochemical

  含有不同取代的二硫富烯基乙烯基单元的新3,3-二苯基-8-（1,4-二硫富烯基-6-基）-[ 3H ]-萘[ 2,1- b ]吡喃衍生物的合成，电化学和光致变色性质为描述。示出了电化学二聚化的一个实例，该实例提供了进入电活性双发色体系的途径。这样的系统可以研究光致变色和电化学性质的相互作用。