1,2-ethanediyl-bis[bis(4-methylthiophenyl)phosphine] | 110391-35-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1,2-ethanediyl-bis[bis(4-methylthiophenyl)phosphine]
• 英文别名: 1,2-Bis(bis(4-(methylthio)phenyl)phosphino)ethane；2-bis(4-methylsulfanylphenyl)phosphanylethyl-bis(4-methylsulfanylphenyl)phosphane
• CAS: 110391-35-0
• 化学式: C₃₀H₃₂P₂S₄
• 分子量: 582.796
• InChiKey: PADSMVGEYSDVMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2-ethanediyl-bis[bis(4-methylthiophenyl)phosphine] 在 sodium 、 氯化铵 作用下， 以 氨 为溶剂， 反应 0.5h， 以71%的产率得到bis(di-(4-thiophenyl)phosphino)ethane
  参考文献：
  名称：

  Synthesis of triarylphosphines having para –SH and –SMe groups

  摘要：

  The phosphines P(C6H4-4-SR)(3) (R = H, Me, 2-C5H9O) and (C6H4-4-SR)(2)PCH2CH2P(C6H4-4-SR)(2) (R = H, Me) have been synthesized. The phosphines with -SMe groups can be prepared by reaction of 4-BrC6H4SMe with either BuLi or magnesium (to generate the corresponding Grignard compound) followed by reaction with PCl3 or Cl2PCH2CH2PCl2, respectively. The methyl group can be eliminated by reaction with sodium in liquid NH3. Other methods of protection/deprotection of the thiol group failed to afford the desired compounds. Reaction of 4-BrC6H4SH with dihydropyrane afforded the protected thiol 4-BrC6H4S-2-C5H9O from which the corresponding phosphine was successfully synthesized. However, attempts to remove the tetrahydropyranyl group by reaction with AgNO3-HCl, gave an insoluble polymer as product. Reaction of P(C6H4SR)(3) (R = H, Me) with Ni(CO)(4) affords the corresponding mono phosphine complex quantitatively. The complex with the unprotected thiol group can be absorbed on a gold surface and the corresponding v(CO) bands were detected by grazing angle Fourier transform infrared reflection absorption spectroscopy (grazing angle FTIR-RAS). Reaction of Rh(acac)(CO)(2) with P(C6H4SR)(3) (R = Me) affords the complex Rh(acac) (CO)(P(C6H4SR)(3)) (R = Me), but if R = H a polymer insoluble in any solvent was obtained. The same occurs in the case of PtCl2(CO)(DMSO). Apparently, once P(C6H4SH)(3) is coordinated to a metal not in the zero oxidation state, oxidation of the thiol group to disulphide becomes very easy even in a dinitrogen atmosphere. (C) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2004.08.031
• 作为产物：
  描述：

  1,2-双(二氯磷基)-乙烷 生成 1,2-ethanediyl-bis[bis(4-methylthiophenyl)phosphine]
  参考文献：
  名称：

  HILL, DAVID T.;JOHNSON, RANDALL K.;MIRABELLI, CHRISTOPHER K.

  摘要：

  DOI：

文献信息

• Antitumor activity of bis(diphenylphosphino)alkanes, their gold(I) coordination complexes, and related compounds
  作者：Christopher K. Mirabelli、David T. Hill、Leo F. Faucette、Francis L. McCabe、Gerald R. Girard、Deborah B. Bryan、Blaine M. Sutton、Joan O. Leary Barus、Stanley T. Crooke、Randall K. Johnson

  DOI：10.1021/jm00395a004

  日期：1987.12

  inactive. Among dppe analogues, replacement of phenyl groups with ethyl or benzyl groups resulted in inactivity for both ligands and the corresponding gold complexes whereas substitution with cyclohexyl or heterocyclic ring systems yielded ligands and/or gold complexes with antitumor activity. Among substituted-phenyl dppe and dppe(AuCl)2 analogues, 3-fluoro, 4-fluoro, perdeuterio, 4-methylthio, and 2-methylthio

  描述了与双（二苯基膦基）乙烷（dppe）有关的双膦及其金配合物，在多种可移植肿瘤模型中具有活性。在第1-5天以最大耐受剂量（MTD）40μmol/ kg腹膜内给药时，dppe可重复产生ip P388白血病小鼠的寿命（ILS）100％。氯金（I）与dppe中的每种膦配位得到的复合物具有相似的活性，但剂量水平比dppe低得多。金（I）配合物的MTD为7μmol/ kg。在dppe的其他金属络合物中，Au（III）络合物具有活性（大于50％ILS），而Ag（I），Ni（II），Pt（II），Pd（II）和Rh（I）络合物具有活性。不活跃。在dppe类似物中，用乙基或苄基取代苯基会导致配体和相应的金络合物均失活，而用环己基或杂环系统取代会产生具有抗肿瘤活性的配体和/或金络合物。在取代的苯基dppe和dppe（AuCl）2类似物中，3-氟，4-氟，氘代，4-甲硫基和2-甲硫基类似物是有活性的。4-甲
• US4766226A
  申请人：——

  公开号：US4766226A

  公开（公告）日：1988-08-23
• US4857549A
  申请人：——

  公开号：US4857549A

  公开（公告）日：1989-08-15
• Synthesis of triarylphosphines having para –SH and –SMe groups
  作者：Fabio Ragaini、Luca Lunardi、Diego Tomasoni、Vittoria Guglielmi

  DOI：10.1016/j.jorganchem.2004.08.031

  日期：2004.11

  The phosphines P(C6H4-4-SR)(3) (R = H, Me, 2-C5H9O) and (C6H4-4-SR)(2)PCH2CH2P(C6H4-4-SR)(2) (R = H, Me) have been synthesized. The phosphines with -SMe groups can be prepared by reaction of 4-BrC6H4SMe with either BuLi or magnesium (to generate the corresponding Grignard compound) followed by reaction with PCl3 or Cl2PCH2CH2PCl2, respectively. The methyl group can be eliminated by reaction with sodium in liquid NH3. Other methods of protection/deprotection of the thiol group failed to afford the desired compounds. Reaction of 4-BrC6H4SH with dihydropyrane afforded the protected thiol 4-BrC6H4S-2-C5H9O from which the corresponding phosphine was successfully synthesized. However, attempts to remove the tetrahydropyranyl group by reaction with AgNO3-HCl, gave an insoluble polymer as product. Reaction of P(C6H4SR)(3) (R = H, Me) with Ni(CO)(4) affords the corresponding mono phosphine complex quantitatively. The complex with the unprotected thiol group can be absorbed on a gold surface and the corresponding v(CO) bands were detected by grazing angle Fourier transform infrared reflection absorption spectroscopy (grazing angle FTIR-RAS). Reaction of Rh(acac)(CO)(2) with P(C6H4SR)(3) (R = Me) affords the complex Rh(acac) (CO)(P(C6H4SR)(3)) (R = Me), but if R = H a polymer insoluble in any solvent was obtained. The same occurs in the case of PtCl2(CO)(DMSO). Apparently, once P(C6H4SH)(3) is coordinated to a metal not in the zero oxidation state, oxidation of the thiol group to disulphide becomes very easy even in a dinitrogen atmosphere. (C) 2004 Elsevier B.V. All rights reserved.
• HILL, DAVID T.;JOHNSON, RANDALL K.;MIRABELLI, CHRISTOPHER K.
  作者：HILL, DAVID T.、JOHNSON, RANDALL K.、MIRABELLI, CHRISTOPHER K.

  DOI：——

  日期：——