(S)-2-((Z)-3-iodo-2-methyl-allyl)-oxirane | 912344-17-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧戊环
• 英文名称: (S)-2-((Z)-3-iodo-2-methyl-allyl)-oxirane
• 英文别名: (2S)-2-[(Z)-3-iodo-2-methylprop-2-enyl]oxirane
• CAS: 912344-17-3
• 化学式: C₆H₉IO
• 分子量: 224.041
• InChiKey: WYZBSPBPQLYXTQ-LMXCLXGDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-2-((Z)-3-iodo-2-methyl-allyl)-oxirane 在 四(三苯基膦)钯 chromium dichloride 、 N-溴代丁二酰亚胺(NBS) 、 copper(l) iodide 、 4 A molecular sieve 、 双氧水 、 sodium hexamethyldisilazane 、 4-甲基苯磺酸吡啶 、 对甲苯磺酸 、 三苯基膦 、 cesium fluoride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 bipinnatin J
  参考文献：
  名称：

  A biomimetic total synthesis of (+)-intricarene

  摘要：

  An asymmetric synthesis of the furanocembrane (-)-bipinnatin J (3a) found in gorgonian corals is described. Treatment of 3a with VO(acaC)(2)-'BuOOH, followed by acetylation, gave acetoxypyranone 15. When 15 was heated in the presence of DBU, it underwent a transannular oxidopyrylium-alkene [5+2] cycloaddition producing the polycyclic diterpene (+)-intricarene 1, isolated from the coral Pseudopterogorgia kallos. The total synthesis of intricarene 1 mimics its most likely biosynthesis via oxidation of bipinnatin J (3a) in vivo. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.06.150
• 作为产物：
  描述：

  (S)-pent-4-yne-1,2-diol 在 吡啶 、 二氯二茂锆 、 potassium carbonate 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 72.0h， 生成 (S)-2-((Z)-3-iodo-2-methyl-allyl)-oxirane
  参考文献：
  名称：

  A biomimetic total synthesis of (+)-intricarene

  摘要：

  An asymmetric synthesis of the furanocembrane (-)-bipinnatin J (3a) found in gorgonian corals is described. Treatment of 3a with VO(acaC)(2)-'BuOOH, followed by acetylation, gave acetoxypyranone 15. When 15 was heated in the presence of DBU, it underwent a transannular oxidopyrylium-alkene [5+2] cycloaddition producing the polycyclic diterpene (+)-intricarene 1, isolated from the coral Pseudopterogorgia kallos. The total synthesis of intricarene 1 mimics its most likely biosynthesis via oxidation of bipinnatin J (3a) in vivo. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.06.150

文献信息

• Total synthesis of (+)-intricarene using a biogenetically patterned pathway from (−)-bipinnatin J, involving a novel transannular [5+2] (1,3-dipolar) cycloaddition
  作者：Bencan Tang、Christopher D. Bray、Gerald Pattenden

  DOI：10.1039/b910572g

  日期：——

  it gave (+)-intricarene 1, which is found in P. kallos, via a novel transannular [5+2] (or 1,3-dipolar) cycloaddition involving the butenolide-oxidopyrylium ion intermediate 31. We believe that this total synthesis of (+)-intricarene 1 mimics its most likely origin in nature viaoxidation of (−)-bipinnatin J (4a), presumably involving photochemically generated singlet oxygen or possibly a P450 monooxygenase

  描述了一种不对称合成的呋喃丁烯内酯基的大环二萜（-）-联吡啶类化合物J（4a），该化合物是从八方正八叶假单胞菌高联杆菌中分离出来的。合成的基础是从（+）-缩水甘油精制手性内酯取代的乙烯基碘化物26b，然后与苯乙烯基糠醛27进行分子间斯蒂勒偶联反应，生成28a，然后进行分子内Nozaki–Hiyama–Kishi烯丙基化反应，28b → 4a。VO（acac）2 – t BuO 2处理（-）-联吡啶J（4a）小时，随后互变异构hydroxypyranone产物的乙酰化7 / 8，下一个得到acetoxypyrone 30。将乙酰氧基吡喃酮30加热至乙腈在DBU存在下，得到（+）-intricarene 1，其存在于P中。kallos，通过一种新颖的跨环式[5 + 2]（或1,3-偶极）环加成反应，涉及丁烯内酯-氧化吡啶鎓离子中间体31。我们相信，（+）-tric香烯1的这种全合成模拟了其最可
• Total synthesis of (+)-Z-deoxypukalide, a furanobutenolide-based cembranoid isolated from the pacific octocoral Leptogorgia spp.
  作者：Bencan Tang、Christopher D. Bray、Gerald Pattenden、Joseph Rogers

  DOI：10.1016/j.tet.2010.01.059

  日期：2010.3

  A total synthesis of (+)-Z-deoxypukalide 3 using a combination of Stille and Nozaki-Hiyama-Kishi(NHK) coupling reactions as key steps, is described. During this study a new practical synthesis of the substituted butenolide intermediate 10, based on a combination of RCM and CM reactions from the cyclobutene ester 21 in the presence of 2-methylpropenol was also developed. Attempts to apply the intramolecular NHK reaction to the substrates 8a and 8b containing an ester group adjacent to the reacting aldehyde functionality gave disappointing low yields (<6%) of the corresponding coupled products 9. The synthetic (+)-Z-deoxypukalide 3 was correlated with naturally derived material, and also with pukalide 1, the first member of the furanobutenolide-based cembranoids to be isolated from corals. (C) 2010 Elsevier Ltd. All rights reserved.