(3aS,4R,5R,6aS)-4-bromo-5-hydroxy-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one | 132747-01-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3aS,4R,5R,6aS)-4-bromo-5-hydroxy-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one
• CAS: 132747-01-4
• 化学式: C₇H₉BrO₃
• 分子量: 221.051
• InChiKey: CERPWPGUJGGBOJ-RASXUPOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3aS,4R,5R,6aS)-4-bromo-5-hydroxy-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one 在 偶氮二异丁腈 、 三正丁基氢锡 、 二甲基亚砜 、 三氟乙酸酐 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 2.33h， 生成 Cyclopent-2-ene-4-one-1-acetic acid
  参考文献：
  名称：

  Synthesis of 3,4-fused cycloalkanopyrroles by 1,3-dipolar cycloaddition

  摘要：

  The synthesis of a number of 3,4-fused cycloalkanopyrroles bearing substituents on the cycloalkane ring was accomplished by 1,3-dipolar cycloaddition. The yield of the cyclization appeared to depend on the base-sensitivity of the Michael acceptor, but the method is applicable across a broad range of cyclic alpha,beta-unsaturated ketone esters. Functional group transformations can be undertaken following pyrrole synthesis to increase the diversity of cycloalkanopyrroles accessible by this method. One pyrrole thus made is a diester of a conformationally-constrained analogue of porphobilinogen, the precursor of the natural tetrapyrroles. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.12.013
• 作为产物：
  描述：

  双环[3.2.0]庚-2-烯-6-酮 在 N-溴代丁二酰亚胺(NBS) 、 水 、 双氧水 、 溶剂黄146 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 生成 (3aS,4R,5R,6aS)-4-bromo-5-hydroxy-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one
  参考文献：
  名称：

  Synthesis of 3,4-fused cycloalkanopyrroles by 1,3-dipolar cycloaddition

  摘要：

  The synthesis of a number of 3,4-fused cycloalkanopyrroles bearing substituents on the cycloalkane ring was accomplished by 1,3-dipolar cycloaddition. The yield of the cyclization appeared to depend on the base-sensitivity of the Michael acceptor, but the method is applicable across a broad range of cyclic alpha,beta-unsaturated ketone esters. Functional group transformations can be undertaken following pyrrole synthesis to increase the diversity of cycloalkanopyrroles accessible by this method. One pyrrole thus made is a diester of a conformationally-constrained analogue of porphobilinogen, the precursor of the natural tetrapyrroles. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.12.013

文献信息

• Baeyer-Villiger Oxidation and Oxidative Cascade Reactions with Aqueous Hydrogen Peroxide Catalyzed by Lipophilic Li[B(C6F5)4] and Ca[B(C6F5)4]2
  作者：Muhammet Uyanik、Daisuke Nakashima、Kazuaki Ishihara

  DOI：10.1002/anie.201204286

  日期：2012.9.3

  Efficient and selective: Two lipophilic catalysts were used for Baeyer–Villiger (BV) oxidations to give lactones in high yields (see scheme). Cascade reactions involving this BV oxidation were used to selectively obtain either unsaturated carboxylic acids or hydroxylactones in high yields from β‐silyl cyclohexanones.

  高效和选择性：两种亲脂性催化剂用于Baeyer-Villiger（BV）氧化，以高收率得到内酯（请参阅方案）。涉及这种BV氧化的级联反应用于从β-甲硅烷基环己酮中高收率选择性地获得不饱和羧酸或羟基内酯。
• Asymmetric Baeyer-Villiger oxidation of cyclobutanones
  作者：Margus Lopp、Anne Paju、Tõnis Kanger、Tõnis Pehk

  DOI：10.1016/0040-4039(96)01666-8

  日期：1996.10

  The asymmetric Baeyer-Villiger oxidation of racemic cyclobutanones 1, 2, and 3 and a prochiral cyclobutanone 4 under Sharpless oxidation conditions resulted in the enantiomeric lactones 5ee 34%, 6ee 53%, 7ee 75% and 8 40% ee respectively.

  外消旋环丁酮1、2和3和前手性环丁酮4在Sharpless氧化条件下的不对称Baeyer-Villiger氧化作用分别导致对映体内酯5 ee 34％，6 ee 53％，7 ee 75％和8 40％ee。
• A simplified synthesis of (+)-brefeldin A
  作者：E.J. Corey、Philip Carpino

  DOI：10.1016/s0040-4039(00)97297-6

  日期：1990.1

  An effective and enantioselective process for the total synthesis of (+)-brefeldin A (1) is described which starts from the dextrorotatory ketone 2.
• Asymmetric oxidation of cyclobutanones: modification of the Sharpless catalyst
  作者：Tõnis Kanger、Kadri Kriis、Anne Paju、Tõnis Pehk、Margus Lopp

  DOI：10.1016/s0957-4166(98)00463-7

  日期：1998.12

  Oxidation of prochiral and racemic cyclobutanones with t-BuOOH and Ti-TADDOL-based complexes afforded lactones in up to 44% ee. The enantioselectivity of the reaction clearly depends on the amount of the reagent and the highest enantioselectivities were obtained with stoichiometric amounts of the complex. Modification of the TADDOL structure and use of the mixed complex derived from TADDOL and a tartaric ester led to more reactive but less selective oxidation systems. (C) 1998 Elsevier Science Ltd. All rights reserved.
• COREY, E. J.;CARPINO, PHILIP, TETRAHEDRON LETT., 31,(1990) N2, C. 7555-7558
  作者：COREY, E. J.、CARPINO, PHILIP

  DOI：——

  日期：——