(3R,1E,5Z)-3-(t-butyldiphenylsilyloxy)-1-iodoocta-1,5-diene | 164524-21-4

• 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: (3R,1E,5Z)-3-(t-butyldiphenylsilyloxy)-1-iodoocta-1,5-diene
• 英文别名: tert-butyl-[(1E,3R,5Z)-1-iodoocta-1,5-dien-3-yl]oxy-diphenylsilane
• CAS: 164524-21-4
• 化学式: C₂₄H₃₁IOSi
• 分子量: 490.5
• InChiKey: VUHLZJAMRUHPMN-NURHRQHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.24
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  (3R,1E,5Z)-3-(t-butyldiphenylsilyloxy)-1-iodoocta-1,5-diene 在 chromium chloride 、 四丙基高钌酸铵 、 nickel dichloride 作用下， 以 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成
  参考文献：
  名称：

  Total Synthesis of Halicholactone and Neohalicholactone¹

  摘要：

  The total synthesis of the marine natural products neohalicholactone (1) and halicholactone (2), in enantiomerically pure form, are reported. Key steps in the synthesis of each compound include a cis-selective Wittig reaction, stereoselective cyclopropanation, nine-membered lactone formation using the Yamaguchi method and late-stage stereoselective Cr(II)/Ni(II) mediated coupling of vinyl iodides 39 and 50 with aldehyde 14. In the case of the neohalicholactone synthesis the two major components which were coupled in this convergent synthesis were each derived from the enantiomers of commercially available malic acid. The synthesis served to confirm the original assignment of absolute configuration which was made by Yamada and Clardy. We also demonstrated, through the preparation of diastereoisomers, that another reported compound closely related to neohalicholactone is likely to be the C-15 epimer 67.

  DOI：

  10.1021/jo962312j
• 作为产物：
  描述：

  (R,Z)-2-[(4-methoxybenzyl)oxy]hept-4-en-1-ol 在 咪唑 、 Schwartz's reagent 、 正丁基锂 、 草酰氯 、 碘 、 二甲基亚砜 、 三乙胺 、 三苯基膦 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 lithium diisopropyl amide 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 35.75h， 生成 (3R,1E,5Z)-3-(t-butyldiphenylsilyloxy)-1-iodoocta-1,5-diene
  参考文献：
  名称：

  Total Synthesis of Halicholactone and Neohalicholactone¹

  摘要：

  The total synthesis of the marine natural products neohalicholactone (1) and halicholactone (2), in enantiomerically pure form, are reported. Key steps in the synthesis of each compound include a cis-selective Wittig reaction, stereoselective cyclopropanation, nine-membered lactone formation using the Yamaguchi method and late-stage stereoselective Cr(II)/Ni(II) mediated coupling of vinyl iodides 39 and 50 with aldehyde 14. In the case of the neohalicholactone synthesis the two major components which were coupled in this convergent synthesis were each derived from the enantiomers of commercially available malic acid. The synthesis served to confirm the original assignment of absolute configuration which was made by Yamada and Clardy. We also demonstrated, through the preparation of diastereoisomers, that another reported compound closely related to neohalicholactone is likely to be the C-15 epimer 67.

  DOI：

  10.1021/jo962312j

文献信息

• Stereocontrolled Total Synthesis of the Potent Anti-inflammatory and Pro-resolving Lipid Mediator Resolvin D3 and Its Aspirin-Triggered 17<i>R</i>-Epimer
  作者：Jeremy W. Winkler、Jasim Uddin、Charles N. Serhan、Nicos A. Petasis

  DOI：10.1021/ol400484u

  日期：2013.4.5

  The first total synthesis of stereochemically pure resolvin D3 and aspirin-triggered resolvin D3 is reported. These enzymatic metabolites of docosahexaenoic acid (DHA) have potent anti-inflammatory and pro-resolving actions. The convergent synthetic strategy is based on enantiomerically pure starting materials, and it is highly stereocontrolled.

  报道了立体化学纯的resolvin D3和阿司匹林触发的resolvin D3的首次全合成。这些二十二碳六烯酸 (DHA) 的酶代谢物具有有效的抗炎和促消退作用。收敛合成策略基于对映异构纯的起始材料，并且是高度立体控制的。
• The total asymmetric synthesis of Halicholactone and Neohalicholactone
  作者：Douglas J. Critcher、Stephen Connolly、Martin Wills

  DOI：10.1016/0040-4039(95)00588-4

  日期：1995.5

  Completion of the first total synthesis of the marine natural products Halicholactone and Neohalicholactone is reported. The key step is a moderately stereoselective coupling between a vinylic anion and an aldehyde. An unexpectedly slow desilylation due to the presence of a proximal hydroxy group is also reported.

  据报道已经完成了海洋天然产物卤代内酯和新卤代内酯的第一个全合成反应。关键步骤是乙烯基阴离子和醛之间的中等立体选择性偶联。还报道了由于近端羟基的存在而出乎意料的缓慢的甲硅烷基化。