triphenylphosphorane | 13504-72-8

• 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: triphenylphosphorane
• 英文别名: ethoxycarbonylcyanomethylenetriphenylphosphorane；Triphenylphosphin-(ethoxycarbonyl-cyan-methylen)；Ethyl cyano(triphenylphosphoranylidene)acetate；ethyl 2-cyano-2-(triphenyl-λ5-phosphanylidene)acetate
• CAS: 13504-72-8
• 化学式: C₂₃H₂₀NO₂P
• 分子量: 373.391
• InChiKey: ZTDOSQRNLVWAJF-UHFFFAOYSA-N

物化性质

• 熔点：
  204-205 °C
• 沸点：
  518.1±33.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  triphenylphosphorane 、 靛红 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 ethyl 2-(2-oxoindolin-3-ylidene)cyanoacetate
  参考文献：
  名称：

  Bioreduction of the C C double bond with Pseudomonas monteilii ZMU-T17: one approach to 3-monosubstituted oxindoles

  摘要：

  An efficient whole cell-mediated bioreduction of 3-methylene-2-oxindoles has been developed, affording a range of 3-monosubstituted oxindoles in moderate to good yields (41-82%) with Pseudomonas monteilii ZMU-T17 as biocatalyst. Additionally, a possible reaction pathway for this bioreduction of C=C double bond was proposed. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2016.04.037
• 作为产物：
  描述：

  (三苯基膦)乙腈 在 三乙胺 作用下， 以 苯 为溶剂， 生成 triphenylphosphorane
  参考文献：
  名称：

  Yalda, R; Rao, V. Subrahmanyeswara; Rao, Jampani Madhusundana, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1982, vol. 21, # 11, p. 1046 - 1048

  摘要：

  DOI：

文献信息

• Alkenylation of Imides and Activated Amides
  作者：Wilhelm FLITSCH、Stefan R. SCHINDLER

  DOI：10.1055/s-1975-23889

  日期：——

  The reaction of imides and activated amides with phosphoranes provides a simple route to enamides, bis[alkenyl]amines, and enamines. Experiments to determine the scope and limitations of these reactions are summarised in this review. Some of the results are taken from investigations with other aims. As well as the dependance on structure, configurational and tautomeric aspects of the reaction are described. The Wittig alkenylation of the imides is compared with other methods of alkenylation. 1. Introduction 2. Wittig Alkenylation of Imides 2.1. General Comments 2.2. Non-Stabilised Phosphoranes 2.3. Ethoxycarbonylmethylenetriphenylphosphorane and Cyanomethylenetriphenylphosphorane 2.3.1. Open Chain Imides 2.3.2. Five-Membered Ring Imides: Phthalimides, Succinimides, and Maleimides 2.3.3. Six-Membered and Larger Ring Imides 2.3.4. Bicyclic N-Bridgehead Imides 2.3.5. N-Acylimides 2.4. Benzoylmethylenetriphenylphosphorane 3. Alkenylation of Imides with the Wittig-Horner Reagent 4. Alkenylation of Activated Amides 4.1. N-Sulfonyllactams 4.2. N-Acylpyrroles 5. Conclusions

  酰亚胺和活化酰胺与磷烯的反应为酞胺、双[烯烃基]胺和烯胺提供了一条简单的合成路线。本文总结了确定这些反应的适用范围和局限性的实验结果。一些结果来自于其他目的的研究。除了对结构的依赖，本文还描述了反应的构象和互变异构方面。将酰亚胺的Wittig烯基化与其他烯基化方法进行了比较。 1. 引言 2. 酰亚胺的Wittig烯基化 2.1. 一般评论 2.2. 非稳定磷烯 2.3. 乙氧羰基亚甲基三苯基磷烯和氰亚甲基三苯基磷烯 2.3.1. 开链酰亚胺 2.3.2. 五元环酰亚胺：邻苯二甲酰亚胺、琥珀酰亚胺和马来酰亚胺 2.3.3. 六元及更大环酰亚胺 2.3.4. 自环桥头N-桥联酰亚胺 2.3.5. N-酰基酰亚胺 2.4. 苯甲酰基亚甲基三苯基磷烯 3. 使用Wittig-Horner试剂对酰亚胺进行烯基化 4. 活化酰胺的烯基化 4.1. N-磺酰亚乳胺 4.2. N-酰基吡咯 5. 结论
• Listvan, V. N.; Stasyuk, A. P.; Kurgan, L. N., Journal of general chemistry of the USSR, 1987, vol. 57, p. 1366 - 1371
  作者：Listvan, V. N.、Stasyuk, A. P.、Kurgan, L. N.

  DOI：——

  日期：——
• YADLA, RAO, V. SUBRAHMANYESWARA;RAO, JAMPANI, MADHUSUDANA, INDIAN J. CHEM., 1982, 21, N 11, 1046-1048
  作者：YADLA, RAO, V. SUBRAHMANYESWARA、RAO, JAMPANI, MADHUSUDANA

  DOI：——

  日期：——
• LISTVAN V. N.; STASYUK A. P.; KURGAN L. N., ZH. OBSHCH. XIMII, 57,(1987) N 7, 1534-1540
  作者：LISTVAN V. N.、 STASYUK A. P.、 KURGAN L. N.

  DOI：——

  日期：——
• Bioreduction of the C C double bond with Pseudomonas monteilii ZMU-T17: one approach to 3-monosubstituted oxindoles
  作者：Jia Zhao、Shuicheng Guan、Xiaojian Zhou、Wenyong Han、Baodong Cui、Yongzheng Chen

  DOI：10.1016/j.tet.2016.04.037

  日期：2016.6

  An efficient whole cell-mediated bioreduction of 3-methylene-2-oxindoles has been developed, affording a range of 3-monosubstituted oxindoles in moderate to good yields (41-82%) with Pseudomonas monteilii ZMU-T17 as biocatalyst. Additionally, a possible reaction pathway for this bioreduction of C=C double bond was proposed. (C) 2016 Elsevier Ltd. All rights reserved.