<(E)-but-2-enylidene>triphenylphosphorane | 56374-57-3

• 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: <(E)-but-2-enylidene>triphenylphosphorane
• 英文别名: (E)-2-butenylidenetriphenylphosphorane；(2-Butenyliden)triphenylphosphoran；crotyltriphenylphosphorane；trans-Allyliden-triphenyl-phosphoran；Phosphorane, 2-butenylidenetriphenyl-, (E)-；[(E)-but-2-enylidene]-triphenyl-λ5-phosphane
• CAS: 56374-57-3
• 化学式: C₂₂H₂₁P
• 分子量: 316.382
• InChiKey: HMYFFMVNLGNNSY-NSCUHMNNSA-N

物化性质

• 沸点：
  466.8±28.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 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：

  <(E)-but-2-enylidene>triphenylphosphorane 、 (2S)-6-乙氧基-1,6-二氧代-2-己烷基苯甲酸酯 生成 [(5S,6Z,8E)-1-ethoxy-1,10-dioxodeca-6,8-dien-5-yl] benzoate
  参考文献：
  名称：

  β-cetophosphonates: Precurseurs d'analogues du LTB4.

  摘要：

  DOI：

  10.1016/s0040-4039(00)97561-0
• 作为产物：
  描述：

  (E)-(but-2-en-1-yl)triphenylphosphonium bromide 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.67h， 生成 <(E)-but-2-enylidene>triphenylphosphorane
  参考文献：
  名称：

  Total Synthesis of Natural and ent-Fredericamycin A

  摘要：

  A total synthesis of both enantiomers of the potent antitumor-antibiotic fredericamycin A (1) is detailed based on a room temperature inverse electron demand Diels-Alder reaction of a N-sulfonyl-1-aza-1,3-butadiene for assemblage of a pyridone F ring precursor, a single-step Michael addition-intramolecular acylation for annulation of the DE ring system onto this pyridone F ring precursor, implementation of a regiospecific chromium carbene benzannulation reaction for AB ring construction, and a simple aldol closure for introduction of the spiro CD ring system. Resolution of the penultimate precursor 41 followed by deprotection provided natural and ent-fredericamycin A. The indistinguishable cytotoxic potency of the two enantiomers (L1210 IC50, 0.03 and 0.04 mu g/mL, respectively) is disclosed along with that of the key partial structures 2 (IC50 = 2 mu g/mL) and 21 IC50 = 7 mu g/mL) constituting the fully functionalized ABCDE and DEF ring systems of the natural product.

  DOI：

  10.1021/ja00153a004

文献信息

• Sterospecific Syntheses and Spectroscopic Properties of Isomeric 2,4,6,8-Undecatetraenes. New Hydrocarbons from the Marine Brown AlgaGiffordia mitchellae. Part IV.
  作者：Wilhelm Boland、Nora Schroer、Christiane Sieler、Martin Feigel

  DOI：10.1002/hlca.19870700415

  日期：1987.7.8

  Giffordene (=(2Z,4Z,6E,8Z)-2,4,6,8-undecatetraene; 9f) and five steroisomers are new C11H16 hydrocarbons from the marine brown alga Giffordia mitchellae. Their synthesis is based on non-stereoselective Wittig reactions of (E)-2-alkenals with appropriate acetylenic phosphoranes and subsequent chromatographic separation of the resulting (E/Z)-pairs. The uniform enynes (>98% purity) are then stereospecifically

  Giffordene（=（2 Z，4 Z，6 E，8 Z）-2,4,6,8-十一碳烯; 9f）和5种立体异构体是来自海洋褐藻Giffordia mitchellae的新C 11 H 16烃。它们的合成基于（E）-2-烯烃与适当的炔基膦烷的非立体选择性Wittig反应，以及随后色谱分离所得的（E / Z）对。然后将均匀的炔烃（> 98％的纯度）在水溶液中用Zn（Cu / Ag）立体定向还原为（Z）烯烃。MeOH在室温13 C-和1给出了新四烯的1 H-NMR数据。从生物合成上，giffordene（9f）通过不稳定的（3 Z，5 Z，8 Z）-1,3,5,8，-十一碳六烯衍生自十二碳3,6,9-三烯酸，然后经热允许的对苯二酚1， 7-σ氢转移至（2 Z，4 Z，6 E，8 Z）-异构体9f。
• Ando, Tetsu; Ogura, Yasushi; Koyama, Motoaki, Agricultural and Biological Chemistry, 1988, vol. 52, # 10, p. 2459 - 2468
  作者：Ando, Tetsu、Ogura, Yasushi、Koyama, Motoaki、Kurane, Michiko、Uchiyama, Masaaki、Seol, Kwang Yaul

  DOI：——

  日期：——
• Ene reactions of conjugated dienes. 2. Dependence of rate on degree of hydrogen removed and s-cis or s-trans diene character
  作者：Barry M. Jacobson、Georgia M. Arvanitis、Carol A. Eliasen、Rimma Mitelman

  DOI：10.1021/jo00202a011

  日期：1985.1
• Synthesis of (2 R ,4 R )- and (2 S ,4 S )-4-hydroxypipecolic acid derivatives and (2 S ,4 S )-(−)-SS20846A
  作者：Mark Sabat、Carl R Johnson

  DOI：10.1016/s0040-4039(00)02124-9

  日期：2001.2

  Syntheses of protected derivatives of both enantiomers of trans-4-hydroxypipecolic acid (2) and the natural product (-)-SS20846A (3) were accomplished from vinylglycinols. Key transformations involved construction of the piperidine ring via ring-closing metathesis (Grubbs' catalyst) and installation of the 4-hydroxy substituent by Prevost reaction. X-Ray diffraction analyses conclusively established the regio- and stereochemistry of key intermediates. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Synthesis of (±)-solanapyrone A
  作者：Akitami Ichihara、Masayoshi Miki、Hiroyuki Tazaki、Sadao Sakamura

  DOI：10.1016/s0040-4039(00)95319-x

  日期：1987.1