(3aS,6aR)-hexahydro-1H-cyclopenta[c]furan-1-one | 121960-86-9

• 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,6aR)-hexahydro-1H-cyclopenta[c]furan-1-one
• 英文别名: hexahydro-1H-cyclopenta[c]furan-1-one；cis-Hexahydro-cyclopenta[c]furan-1-one；(3aR,6aS)-1,3a,4,5,6,6a-hexahydrocyclopenta[c]furan-3-one
• CAS: 121960-86-9
• 化学式: C₇H₁₀O₂
• 分子量: 126.155
• InChiKey: WAWXKXJCQYNDFY-PHDIDXHHSA-N

物化性质

• 沸点：
  254.8±8.0 °C(Predicted)
• 密度：
  1.141±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  9
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-环戊烯甲醛 在 ruthenium trichloride 、 氢氧化钾 、 sodium periodate 、 (S)-2-(piperidinomethyl)pyrrolidine dihydroiodide 、 oxonium 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 (3aS,6aR)-hexahydro-1H-cyclopenta[c]furan-1-one
  参考文献：
  名称：

  Chiral pyrrolidinium salts as organocatalysts in the stereoselective 1,4-conjugate addition of N-methylpyrrole to cyclopent-1-ene carbaldehyde

  摘要：

  A variety of enantiopure proline derived pyrrolidinium (HX)(n) salts have been found to catalyse the 1,4-conjugate addition of AT-methylpyrrole to cyclopent-1-ene carbaldehyde with, in some cases, high diastereo- and enantioselectivity. Parameters such as water activity, choice of acidic cocatalyst (HX)(n) and also the amount of cocatalyst used turned out to be crucial for the diastereo- and enantioselectivity of the reaction. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.11.020

文献信息

• AN ASYMMETRIC SYNTHESIS OF BICYCLIC LACTONES AND ITS APPLICATION TO THE ASYMMETRIC SYNTHESIS OF (1<i>R</i>,3<i>S</i>)-<i>CIS</i>-CHRYSANTHEMIC ACID
  作者：Teruaki Mukaiyama、Hiroyuki Yamashita、Masatoshi Asami

  DOI：10.1246/cl.1983.385

  日期：1983.3.5

  derived from (R)-(−)-2-amino-2-phenylethanol and meso-cyclic-1,2-cis-dicarboxylic acids, by successive treatment with sodium bis(2-methoxyethoxy)aluminum hydride and sodium borohydride, followed by acid hydrolysis. This reaction is successfully applied to the asymmetric synthesis of (1R,3S)-cis-chrysanthemic acid.

  旋光双环内酯是由衍生自 (R)-(-)-2-amino-2-phenylethanol 和 meso-cyclic-1,2-cis-di 二羧酸的 ircides 合成的，通过用双（2-甲氧基乙氧基）钠连续处理)氢化铝和硼氢化钠，然后酸水解。该反应成功应用于(1R,3S)-顺式菊酸的不对称合成。
• (Salen)ruthenium-Catalyzed Desymmetrization of<i>Meso</i>-Diols: Catalytic Aerobic Asymmetric Oxidation under Photo-Irradiation
  作者：Hideki Shimizu、Kenya Nakata、Tsutomu Katsuki

  DOI：10.1246/cl.2002.1080

  日期：2002.11

  Catalytic aerobic oxidation of meso-diols using (nitrosyl)Ru(salen) 7 as the catalyst under photo-irradiation proceeded with moderate enantioselectivity (up to 67% ee) to give the corresponding lactols.

  使用(亚硝酰基)Ru(salen) 7作为催化剂，在光照射下进行中二醇的催化好氧氧化反应，以中等对映选择性（最高达67% ee）生成相应的乳醇。
• Total Synthesis of (+)-Brefeldin C, (+)-nor-Me Brefeldin A and (+)-4-<i>epi</i>-nor-Me Brefeldin A
  作者：Sylvie Archambaud、Frédéric Legrand、Karine Aphecetche-Julienne、Sylvain Collet、André Guingant、M. Evain

  DOI：10.1002/ejoc.200901233

  日期：2010.3

  A total synthesis of (+)-brefeldin C (BFC) and two brefeldin A (BFA) analogues - (+)-nor-Me BFA and (+)-4-epi-nor-Me BFA - has been developed. Key features of the syntheses include desymmetrization of meso anhydrides, a Carreira reaction to control the absolute configuration at C4 of BFC, a Suzuki-Miyaura cross-coupling reaction to create the C11-C12 bond and a Yamaguchi reaction to form the 13-membered

  (+)-brefeldin C (BFC) 和两种 brefeldin A (BFA) 类似物 - (+)-nor-Me BFA 和 (+)-4-epi-nor-Me BFA - 的全合成已经开发出来。合成的关键特征包括内消旋酐的去对称化、控制 BFC C4 绝对构型的 Carreira 反应、产生 C11-C12 键的 Suzuki-Miyaura 交叉偶联反应和形成 13 元内酯的 Yamaguchi 反应戒指。
• Regiodivergent Baeyer–Villiger oxidation of fused ketone substrates by recombinant whole-cells expressing two monooxygenases from Brevibacterium
  作者：Marko D. Mihovilovic、Peter Kapitán

  DOI：10.1016/j.tetlet.2004.02.036

  日期：2004.3

  Microbial Baeyer–Villiger oxidations of fused bicyclic ketones with a cyclobutanone structural motif were investigated using recombinant Escherichia coli cells expressing two monooxygenases from Brevibacterium. In a kinetic resolution process fused ketones were transformed to regioisomeric lactones: ‘normal’ lactones were generated by migration of the more substituted carbon atom and ‘abnormal’ lactones

  利用表达来自短杆菌属的两种单加氧酶的重组大肠杆菌细胞，研究了具有环丁酮结构基序的稠合双环酮的微生物拜耶-维利格氧化。在动力学拆分过程中，将融合的酮转化为区域异构内酯：“正常”内酯是由取代度较高的碳原子迁移产生的，“异常”内酯是由取代度较低的碳原子迁移引起的。两种Baeyer-Villigerases对区域发散性的生物转化显示出明显不同的立体选择性。
• Microbial Transformations 16. One-step synthesis of a pivotal prostaglandin chiral synthon via a highly enantioselective microbiological Baeyer-Villiger type reaction
  作者：Véronique Alphand、Alain Archelas、Roland Furstoss

  DOI：10.1016/s0040-4039(01)80476-7

  日期：1989.1

  The bioconversion of bicyclo[3.2.0]hept-2-en-6-one is described. Each one of its enantiomers affords a different lactone via a highly regio and enantiospecific Baeyer-Villiger type process.

  描述了双环[3.2.0] hept-2-en-6-one的生物转化。它的每个对映异构体通过高度区域性和对映特异性的Baeyer-Villiger型工艺提供不同的内酯。