Cyclohexylmethylen-triphenyl-phosphoran | 21960-28-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Cyclohexylmethylen-triphenyl-phosphoran
• 英文别名: Hexahydrobenzyliden-triphenylphosphoran；Cyclohexylmethylidene(triphenyl)-lambda5-phosphane；cyclohexylmethylidene(triphenyl)-λ5-phosphane
• CAS: 21960-28-1
• 化学式: C₂₅H₂₇P
• 分子量: 358.463
• InChiKey: JGFBIAMWZVORBG-UHFFFAOYSA-N

物化性质

• 沸点：
  514.7±33.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 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：

  Cyclohexylmethylen-triphenyl-phosphoran 以 苯 为溶剂， 生成 <α-Cyclohexyl-β,β-bis-(ethylthio)-vinyl>-triphenylphosphoniumiodid
  参考文献：
  名称：

  Bestmann,H.J. et al., Angewandte Chemie, 1966, vol. 78, p. 1100

  摘要：

  DOI：
• 作为产物：
  描述：

  Triphenyl-hexahydrobenzyl-phosphonium 在 sodium amide 、 六甲基二硅氮烷 作用下， 以 苯 为溶剂， 生成 Cyclohexylmethylen-triphenyl-phosphoran
  参考文献：
  名称：

  新合成三氟甲基丙酮等

  摘要：

  我们报告了一种制备三氟甲基酮的新方法，作为使用有机金属的替代方法。磷酰基yl与三氟乙酸三甲基甲硅烷基酯的缩合提供甲硅烷氧基烯醇醚，其水解导致形成三氟甲基酮。相同的甲硅烷氧基烯醇醚的溴化也是γ-溴三氟甲基酮的方便制备。

  DOI：

  10.1016/s0022-1139(00)82782-7

文献信息

• Substituted dienes prepared from betulinic acid – Synthesis, cytotoxicity, mechanism of action, and pharmacological parameters
  作者：Jan Pokorný、Denisa Olejníková、Ivo Frydrych、Barbora Lišková、Soňa Gurská、Sandra Benická、Jan Šarek、Jana Kotulová、Marián Hajdúch、Petr Džubák、Milan Urban

  DOI：10.1016/j.ejmech.2021.113706

  日期：2021.11

  synthesized from betulinic acid by its oxidation to 30-oxobetulinic acid followed by the Wittig reaction. Cytotoxicity of all compounds was tested in vitro in eight cancer cell lines and two noncancer fibroblasts. Almost all dienes were more cytotoxic than betulinic acid. Compounds 4.22, 4.30, 4.33, 4.39 had IC50 below 5 μmol/L; 4.22 and 4.39 were selected for studies of the mechanism of action. Cell cycle

  通过将桦木酸氧化为 30-氧代桦木酸，然后进行 Wittig 反应，合成了一组新的取代二烯。在八种癌细胞系和两种非癌成纤维细胞中体外测试了所有化合物的细胞毒性。几乎所有的二烯都比桦木酸更具细胞毒性。化合物4.22、4.30、4.33、4.39的IC 50低于5 μmol / L ；选择4.22和4.39进行作用机制研究。细胞周期分析显示在 5 × IC 50时凋亡细胞数量增加浓度，其中可以预期导致细胞死亡的不可逆变化的激活。既4.22和4.39导致细胞在用DNA / RNA合成的部分抑制的G0 / G1期的累积为1×IC 50，并在5几乎完全抑制×IC 50。有趣的是，化合物4.39 在 5 × IC 50导致细胞在 S 期积累。较高浓度的受试药物可能比较低浓度抑制更多的脱靶。破坏细胞代谢的机制可以诱导细胞在 S 期的积累。化合物4.22和4.39 均在癌细胞中引发选择性凋亡通过内在途径，
• Short and efficient preparation of trifluoromethyl vinyl sulphides
  作者：Jean-Pierre Bégué、Danièle Bonnet-Delpon、Abderrahim M'Bida

  DOI：10.1016/s0040-4039(00)61556-3

  日期：1993.11

  S-Alkyl trifluorothioacetate 2 reacts with stabilized and non-stabilized phosphoranes 1 to afford a new and general route to a wide range of trifluoromethyl vinyl sulphides 3. Until now, no general methods allowed the preparation of these interesting compounds.

  S-烷基trifluorothioacetate 2层发生反应以稳定的和未稳定化膦1，得到一种新的和一般途径的广泛的三氟甲基乙烯基硫化物3。迄今为止，还没有通用的方法可以制备这些有趣的化合物。
• A Novel<i>bis</i>-Lactonisation of Naphtho- and Phenanthro-1,2-Dioxines with Malonate­ Nucleophiles
  作者：Dennis K. Taylor、Ben Greatrex、Martyn Jevric、Marc C. Kimber、Sara J. Krivickas、Edward R. Tiekink

  DOI：10.1055/s-2003-38073

  日期：——

  mild to rearrange the 1,2-dioxines to yield the transient cis-γ-hydroxy enone species with no further Kornblum-DeLaMare rearrangement. The cis-γ-hydroxy enones readily undergo conjugate addition by malonate nucleophiles in a highly diastereoselective fashion. An intramolecular domino cyclisation then ensues yielding the observed bis-lactones. The relative configuration of the bis-lactone series was established

  丙二酸亲核试剂以共轭方式添加到取代的萘并 phenanthro-1,2-dioxines 中，以高产率和高 de 提供官能化双内酯。丙二酸亲核试剂的碱性足够温和，可以重新排列 1,2-二恶英，从而产生瞬态的 cis-γ-羟基烯酮物质，而无需进一步的 Kornblum-DeLaMare 重排。顺式-γ-羟基烯酮很容易通过丙二酸亲核试剂以高度非对映选择性的方式进行共轭加成。然后发生分子内多米诺环化，产生观察到的双内酯。双内酯系列的相对构型通过1-和2-D 1 H, 1 3 C NMR技术确定，并通过单晶X射线分析进一步证实。
• Geiparvarin analogs. 2. Synthesis and cytostatic activity of 5-(4-arylbutadienyl)-3(2H)-furanones and of N-substituted 3-(4-oxo-2-furanyl)-2-buten-2-yl carbamates
  作者：Daniele Simoni、Stefano Manfredini、Mojgan Aghazadeh Tabrizi、Rita Bazzanini、Pier G. Baraldi、Jan Balzarini、Erik De Clercq

  DOI：10.1021/jm00115a004

  日期：1991.11

  In an attempt to determine some of the structural features of geiparvarin (1) that account for its cytostatic activity in vitro, a series of geiparvarin analogues (10a-i, 1, 12, and 14-16) which contain novel modifications in the region of the olefinic double bond and of the coumarin moiety have been designed and synthesized. Among the derivatives containing a carbamate moiety, only the analogues containing a carbamate group linked to an alkyl moiety 10b-i were endowed with potent cytostatic activity, whereas the corresponding benzene derivative 10a was devoid of any antiproliferative activity. 6-Methoxygeiparvarin 101 proved equally effective as geiparvin (1), while compounds containing an additional double bond at the side chain (12 and 14-16) were invariably 5-100-fold less effective than geiparvarin. Diene derivative 15, bearing a coumarin moiety, was essentially inactive against murine (L1210, FM3A) tumor cells but exhibited good activity against human (Molt/4F, MT-4) tumor cells.
• Bestmann,H.J. et al., Chemische Berichte, 1979, vol. 112, p. 28 - 41
  作者：Bestmann,H.J. et al.

  DOI：——

  日期：——