6-formyl-3-oxa-bicyclo[3.1.0]hexane-2-one

• 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: 6-formyl-3-oxa-bicyclo[3.1.0]hexane-2-one
• 英文别名: (1S*,5S*,6S*)-6-carbaldehyde-3-oxabicyclo[3.1.0]hexan-2-one；(1S,5S,6S)-2-oxo-3-oxabicyclo[3.1.0]hexane-6-carbaldehyde
• 化学式: C₆H₆O₃
• 分子量: 126.112
• InChiKey: STQWCQBIIKPOSB-VAYJURFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-formyl-3-oxa-bicyclo[3.1.0]hexane-2-one 在 咪唑 、 sodium tetrahydroborate 、 二异丁基氢化铝 、 三乙胺 作用下， 以 甲醇 、 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 23.92h， 生成 Hexadecanoic acid (1R,2R,3S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-3-hexadecanoyloxymethyl-cyclopropylmethyl ester
  参考文献：
  名称：

  Synthesis and Supramolecular Properties of Conformationally Restricted and Flexible Phospholipids

  摘要：

  Short synthetic routes are described to produce structurally related phospholipids that are either conformationally restricted or flexible. The conformationally restricted structures have a cyclopropyl ring in the interfacial region of the phospholipid. The key synthetic step is a cyclopropanation reaction between 2(5H)-furanone and a stabilized chloroallylic phosphonate anion. The synthetic routes enable the incorporation of different polar headgroups as well as nonpolar tails at late stages in the sequence. The phosphoethanolamine derivatives 1b and 2b readily form encapsulating vesicles, however, dye leakage from vesicles composed of the restricted phospholipid 1b is significantly slower than from vesicles composed of flexible analogue 2b. Physicochemical analyses using P-31 NMR, differential scanning calorimetry, fluorescence anisotropy, and Langmuir-Blodgett films suggest that the decreased permeability of membranes composed of conformationally restricted 1b is due to its ability to pack more closely in a bilayer assembly.

  DOI：

  10.1021/jo034843v
• 作为产物：
  描述：

  diisopropyl [2-(2-oxo-3-oxa-bicyclo[3.1.0]hex-6-yl)-vinyl]-phosphonate 在 氧气 、 臭氧 、 二甲基硫 作用下， 以 二氯甲烷 为溶剂， 反应 25.0h， 以61%的产率得到6-formyl-3-oxa-bicyclo[3.1.0]hexane-2-one
  参考文献：
  名称：

  Synthesis and Supramolecular Properties of Conformationally Restricted and Flexible Phospholipids

  摘要：

  Short synthetic routes are described to produce structurally related phospholipids that are either conformationally restricted or flexible. The conformationally restricted structures have a cyclopropyl ring in the interfacial region of the phospholipid. The key synthetic step is a cyclopropanation reaction between 2(5H)-furanone and a stabilized chloroallylic phosphonate anion. The synthetic routes enable the incorporation of different polar headgroups as well as nonpolar tails at late stages in the sequence. The phosphoethanolamine derivatives 1b and 2b readily form encapsulating vesicles, however, dye leakage from vesicles composed of the restricted phospholipid 1b is significantly slower than from vesicles composed of flexible analogue 2b. Physicochemical analyses using P-31 NMR, differential scanning calorimetry, fluorescence anisotropy, and Langmuir-Blodgett films suggest that the decreased permeability of membranes composed of conformationally restricted 1b is due to its ability to pack more closely in a bilayer assembly.

  DOI：

  10.1021/jo034843v

文献信息

• Synthesis of Novel Nucleosides with a Fused Cyclopropane Ring Substituted by a Hydroxymethyl Group
  作者：Cyrille Lescop、François Huet

  DOI：10.1016/s0040-4020(00)00174-5

  日期：2000.5

  3-oxabicyclo[3.1.0]hexan-2-ol 21a–b with the cyclopropane ring substituted by a hydroxymethyl group were synthesized from both products 17a and 18a obtained from the bromohydroxylation of epoxide 16a derived from 3-oxabicyclo[3.2.0]hept-6-en-2-one 15. This preparation involved two stereospecific C4–C3 ring contractions leading to cis,cis-trisubstituted cyclopropane compounds 18a and 12. The hydroxylactols

  从由3-氧杂双环衍生的环氧化物16a的溴羟基化反应得到的产物17a和18a合成了3-氧杂双环[3.1.0]己-2-醇21a - b的两个非对映体，其中环丙烷环被羟甲基取代。[3.2.0] hept-6-en-2-one 15。该制备涉及两个立体特异性C 4 -C 3环收缩，导致顺式，顺式-三取代的环丙烷化合物18a和12。羟基肌醇21a – b如此获得的产物被二乙酰化，单一产物22在异头位置被保护的或游离的碱取代，在每种情况下仅提供一种可能的产物。用氨脱保护得到新的双环核苷11a - d。
• Synthesis of conformationally constrained potential inhibitors of mammalian metalloproteinases
  作者：Stephen Hanessian、Andrew Griffin、Pratik V Devasthale

  DOI：10.1016/s0960-894x(97)10171-8

  日期：1997.12

  The synthesis of carbocyclic molecules containing functional groups capable of interacting with appropriate binding sites in certain metalloproteinases is described. Preliminary biological evaluation reveals modest inhibitory activity for a thioether analog in the trisubstituted cyclopropane series. (C) 1997 Elsevier Science Ltd.
• Synthesis and Supramolecular Properties of Conformationally Restricted and Flexible Phospholipids
  作者：Lauri Vares、Atanas V. Koulov、Bradley D. Smith

  DOI：10.1021/jo034843v

  日期：2003.12.1

  Short synthetic routes are described to produce structurally related phospholipids that are either conformationally restricted or flexible. The conformationally restricted structures have a cyclopropyl ring in the interfacial region of the phospholipid. The key synthetic step is a cyclopropanation reaction between 2(5H)-furanone and a stabilized chloroallylic phosphonate anion. The synthetic routes enable the incorporation of different polar headgroups as well as nonpolar tails at late stages in the sequence. The phosphoethanolamine derivatives 1b and 2b readily form encapsulating vesicles, however, dye leakage from vesicles composed of the restricted phospholipid 1b is significantly slower than from vesicles composed of flexible analogue 2b. Physicochemical analyses using P-31 NMR, differential scanning calorimetry, fluorescence anisotropy, and Langmuir-Blodgett films suggest that the decreased permeability of membranes composed of conformationally restricted 1b is due to its ability to pack more closely in a bilayer assembly.