(2S,3R,4R)-tribenzyloxy-octa-5(Z),7-diene-1-al | 116498-65-8

• 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: (2S,3R,4R)-tribenzyloxy-octa-5(Z),7-diene-1-al
• 英文别名: (2R,3S,4R,5Z)-2,3,4-tris(phenylmethoxy)octa-5,7-dienal
• CAS: 116498-65-8
• 化学式: C₂₉H₃₀O₄
• 分子量: 442.555
• InChiKey: LIXSPXSMHJXSFI-YFSKQJPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  33
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3R,4R)-tribenzyloxy-octa-5(Z),7-diene-1-al 生成 (3S,4R,5R)-tribenzyloxy-nona-1,6(Z),8-triene
  参考文献：
  名称：

  HERCZEGH, PAL;ZSELY, MARTINA;SZILAGYI, LASZLO;BATTA, GYULA;BAJZA, ISTVAN;+, TETRAHEDRON, 45,(1989) N, C. 2793-2802

  摘要：

  DOI：
• 作为产物：
  描述：

  (2R,3S,4R)-tribenzyloxy-octa-5(Z),7-diene-1-al diethyl dithioacetal 生成 (2S,3R,4R)-tribenzyloxy-octa-5(Z),7-diene-1-al
  参考文献：
  名称：

  HERCZEGH, PAL;ZSELY, MARTINA;SZILAGYI, LASZLO;BATTA, GYULA;BAJZA, ISTVAN;+, TETRAHEDRON, 45,(1989) N, C. 2793-2802

  摘要：

  DOI：

文献信息

• Intramolecular reactions of compounds derived from sugars. Part II.1 Stereo-controlled intramolecular diels-alder cyclizations of 16(E,Z),8-nonatrienes and 1-AZA-6(E,Z),8-nonatrienes
  作者：Pál Herczegh、Martina Zsély、László Szilágyi、Gyula Batta、István Bajza、Rezső Bognár

  DOI：10.1016/s0040-4020(01)80109-5

  日期：1989.1

  Intramolecular Diels-Alder reactions of E,Z mixtures of nonatrienes 6 and 9 led to the exclusive formation of the bicyclic compounds 10 and 11 respectively.

  壬基6和9的E，Z混合物的分子内Diels-Alder反应分别导致双环化合物10和11的排他性形成。
• Complete stereoselectivity in the intramolecular diels-alder reactionof a triene derivative from d-xylose
  作者：Pál Herczegh、Martina Zsély、László Szilágyi、Rezső Bognár

  DOI：10.1016/s0040-4039(00)80127-6

  日期：1988.1
• Stability of regioisomeric sugar allyltins. Cleavage of the carbon oxygen bond under radical conditions
  作者：Sławomir Jarosz、Katarzyna Szewczyk

  DOI：10.1016/s0040-4039(01)00239-8

  日期：2001.4

  Secondary sugar allyltin derivatives [Sug-CH(SnBu3)-CH=CH2] decompose at high temperature (140 degreesC) with elimination of the tin moiety and opening of the sugar ring. The cis-dienoaldehydes thus formed react with Ph3P=CH-CO2Me to afford the corresponding trienes, which spontaneously undergo stereoselective intramolecular [4+2] cycloaddition to optically pure, highly oxygenated bicyclo[4.3.0]nonene derivatives. Primary sugar allyltins [Sug-CH=CHCH2-SnBu3] are thermally stable and do not decompose up to 170 degreesC. (C) 2001 Elsevier Science Ltd. All rights reserved.
• HERCZEGH, PAL;ZSELY, MARTINA;SZILAGYI, LASZLO;BATTA, GYULA;BAJZA, ISTVAN;+, TETRAHEDRON, 45,(1989) N, C. 2793-2802
  作者：HERCZEGH, PAL、ZSELY, MARTINA、SZILAGYI, LASZLO、BATTA, GYULA、BAJZA, ISTVAN、+

  DOI：——

  日期：——
• Synthesis of highly oxygenated enantiomerically pure cis-bicyclo[4.3.0]nonanes from secondary sugar allyltin derivatives
  作者：Sławomir Jarosz、Katarzyna Szewczyk、Anna Zawisza

  DOI：10.1016/s0957-4166(03)00310-0

  日期：2003.6

  Secondary sugar allyltin derivatives of the D-series: Sug-CH(SnBu3)-CH=CH2 (obtained in an S(N)2' reaction of the corresponding primary allylic mesylates with 'Bu3SnCu') with the S-configuration at the stereogenic center bearing the -SnBu3 group decompose at 140degreesC to dienoaldehydes: CH2=CH-CH=CH-[(CHOR)(3)]-CHO with the cis geometry across the internal double bond. Such aldehydes react with the stabilized Wittig reagents to afford trienes, cyclization of which provides highly oxygenated enantiomerically pure cis-bicyclo[4.3.0]nonenes. This methodology is complementary to that recently proposed by us leading to such bicyclic systems, but with the trans junction between the five- and six-membered rings. (C) 2003 Elsevier Science Ltd. All rights reserved.