(E)-1-iodo-11-<(tert-butyldimethylsilyl)oxy>-1-undecene | 129056-86-6

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (E)-1-iodo-11-<(tert-butyldimethylsilyl)oxy>-1-undecene
• 英文别名: (E)-11-(tert-butyldimethylsilyloxy)-1-iodoundec-1-ene；(E)-tert-butyl(11-iodoundec-10-enyloxy)dimethylsilane；tert-butyl-[(E)-11-iodoundec-10-enoxy]-dimethylsilane
• CAS: 129056-86-6
• 化学式: C₁₇H₃₅IOSi
• 分子量: 410.454
• InChiKey: KSAXPJWFBSMERO-FYWRMAATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.08
• 重原子数：
  20
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-1-iodo-11-<(tert-butyldimethylsilyl)oxy>-1-undecene 在 四氢吡咯 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 正丁基锂 、 四丁基氟化铵 、 三氧化硫吡啶 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 20.25h， 生成 (S)-(+)-akolactone B
  参考文献：
  名称：

  Synthesis of both enantiomers of akolactone B and (+)-ancepsenolide

  摘要：

  The syntheses of (+)- and (-)-akolactone B and (+)-ancepsenolide were accomplished using a Pd-catalyzed carbonylation. As to the absolute configuration of akolactone B, making a comparison of the specific rotation of both enantiomers of synthetic akolactone B and the natural compound suggests that the absolute configuration at the 4-position of akolactone B is (R). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.08.008
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 咪唑 、 Schwartz's reagent 、 碳酸氢钠 、 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 、 丙酮 为溶剂， 反应 21.5h， 生成 (E)-1-iodo-11-<(tert-butyldimethylsilyl)oxy>-1-undecene
  参考文献：
  名称：

  Synthesis of both enantiomers of akolactone B and (+)-ancepsenolide

  摘要：

  The syntheses of (+)- and (-)-akolactone B and (+)-ancepsenolide were accomplished using a Pd-catalyzed carbonylation. As to the absolute configuration of akolactone B, making a comparison of the specific rotation of both enantiomers of synthetic akolactone B and the natural compound suggests that the absolute configuration at the 4-position of akolactone B is (R). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.08.008

文献信息

• Synthesis of E-vinyl iodides via Pd-catalyzed hydrostannation of terminal alkynes
  作者：Alla Darwish、J. Michael Chong

  DOI：10.1016/j.tet.2011.10.104

  日期：2012.1

  E-Vinyl iodides may be prepared via a one-pot reaction involving Pd-catalyzed hydrostannation of terminal alkynes followed by iodinolysis of the intermediate vinylstannane. The synthesis is tolerant of functional groups, such as alcohols and esters.

  E-乙烯基碘化物可通过一锅反应制备，该反应包括钯催化末端炔烃的氢化锡锡烷化反应，然后对中间乙烯基锡烷进行碘解。该合成耐受官能团，例如醇和酯。
• Synthesis of .beta.-resorcylic macrolides via organopalladium chemistry. Application to the total synthesis of (S)-zearalenone
  作者：A. Kalivretenos、J. K. Stille、L. S. Hegedus

  DOI：10.1021/jo00008a053

  日期：1991.4

  The beta-resorcylic macrolides are a class of naturally occurring 12- and 14-membered macrolides. Zearalenone (1), a 14-membered macrolide of this type, displays useful biological activity, which has led to great synthetic interest. In this paper the intramolecular coupling reaction of an organostannane with an electrophile is used to construct beta-resorcylic macrolides. The intramolecular coupling of an aryl iodide with a vinylstannane provided the highest yield of lactones. This methodology was then used to prepare (S)-zearalenone (1).
• DOOLITTLE, R. E.;BRABHAM, A.;TUMLINSON, J. H., J. CHEM. ECOL., 16,(1990) N, C. 1131-1153
  作者：DOOLITTLE, R. E.、BRABHAM, A.、TUMLINSON, J. H.

  DOI：——

  日期：——
• KALIVRETENOS, A.;STILLE, J. K.;HEGEDUS, L. S., J. ORG. CHEM., 56,(1991) N, C. 2883-2894
  作者：KALIVRETENOS, A.、STILLE, J. K.、HEGEDUS, L. S.

  DOI：——

  日期：——