(1R,5R,8R)-8-Hydroxy-2-oxabicyclo[3.3.0]oct-6-en-3-one | 261630-98-2

• 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: (1R,5R,8R)-8-Hydroxy-2-oxabicyclo[3.3.0]oct-6-en-3-one
• 英文别名: (3aR,6R,6aR)-3,3a,6,6a-Tetrahydro-6-hydroxy-2H-cyclopenta[b]furan-2-one；(3aR,6R,6aR)-6-hydroxy-3,3a,6,6a-tetrahydrocyclopenta[b]furan-2-one
• CAS: 261630-98-2
• 化学式: C₇H₈O₃
• 分子量: 140.139
• InChiKey: RLCFLOOMBMSCFI-HBPOCXIASA-N

物化性质

• 沸点：
  355.4±42.0 °C(Predicted)
• 密度：
  1.390±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  (1R,5R,8R)-8-Hydroxy-2-oxabicyclo[3.3.0]oct-6-en-3-one 在 diisobutylaluminum hydride 、 zinc dibromide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成
  参考文献：
  名称：

  Modular, Well-Behaved Reversible Polymers from DNA-Based Monomers

  摘要：

  DOI：

  10.1002/1521-3773(20021104)41:21<4026::aid-anie4026>3.0.co;2-e
• 作为产物：
  描述：

  1(R),5(S)-7(R),8(R)-dihydroxy-2-oxabicyclo[3.3.0]oct-3-one 在 氢溴酸 、 乙酸酐 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 甲醇 、 乙酰氯 作用下， 以 四氢呋喃 为溶剂， 以84%的产率得到(1R,5R,8R)-8-Hydroxy-2-oxabicyclo[3.3.0]oct-6-en-3-one
  参考文献：
  名称：

  Modular, Well-Behaved Reversible Polymers from DNA-Based Monomers

  摘要：

  DOI：

  10.1002/1521-3773(20021104)41:21<4026::aid-anie4026>3.0.co;2-e

文献信息

• Aminocyclopentanols as sugar mimics. Synthesis from unsaturated bicyclic lactones by Overman rearrangement
  作者：Marie Bøjstrup、Mette Fanefjord、Inge Lundt

  DOI：10.1039/b710232a

  日期：——

  Bicyclic cyclopentane lactones, prepared from bromodeoxyaldonolactones, were transformed into aminocyclopentanols with an Overman rearrangement as the key step. Two of the compounds prepared, 7 and 19, were found to be good inhibitors of jack bean α-mannosidase and β-D-N-acetylglucosaminidase, respectively.

  由溴脱氧醛酮内酯制备的双环环戊烷内酯通过Overman重排关键步骤转化为氨基环戊醇。合成的两种化合物7和19分别被发现对金豆α-甘露糖苷酶和β-D-N-乙酰氨基葡萄糖苷酶具有良好的抑制作用。
• Synthesis of aminocyclopentanols: α-d-galacto configured sugar mimics
  作者：Marie Bøjstrup、Inge Lundt

  DOI：10.1039/b501824b

  日期：——

  Four aminocyclopentanols, as mimics of putative intermediates in the hydrolysis of α-D-galactosides, have been synthesized through a number of stereoselective transformations using the cis-fused cyclopentane-1,4-lactone (1R, 5S, 7R, 8R)-7,8-dihydroxy-2-oxabicyclo[3.3.0]oct-3-one 1 as a chiral building block. The compounds were tested towards various glycosidases but showed no anomer selectivity in the inhibition of α- and β-galactosidases.

  以顺式融合的环戊烷-1,4-内酯（1R, 5S, 7R, 8R）-7,8-二羟基-2-氧杂双环[3.3.0]辛-3-酮 1 为手性结构单元，通过一系列立体选择性转化合成了四种氨基环戊醇，它们是δ-D-半乳糖苷水解过程中假定中间体的模拟物。这些化合物针对各种糖苷酶进行了测试，但在抑制δ-和²-半乳糖苷酶方面没有显示出同分异构体的选择性。
• Synthesis of carbasugars from aldonolactones. Part II. Preparation of polyhydroxy/aminocyclopentanes functionalised at all five ring carbons
  作者：Steen K. Johansen、Inge Lundt

  DOI：10.1039/a907008g

  日期：——

  Starting from (1R,5R,8R)-8-acetoxy-2-oxabicyclo[3.3.0]oct-6-en-3-one 4 the syntheses of 5-deoxy-4a(R)-hydroxy-4a-carba-α-D-ribo-hexofuranose 17, 5-deoxy-4a(R)-hydroxy-4a-carba-α-D-lyxo-hexofuranose 21, 5-deoxy-4a(R)-hydroxy-4a-carba-α-D-xylo-hexofuranose 23 and 4a(R)-hydroxy-2-amino-2,5-dideoxy-4a(R)-hydroxy-4a-carba-α-D-arabino-hexofuranose 1 have been achieved. The methodology included OsO4-catalysed dihydroxylation as well as regioselective epoxide opening followed by calcium borohydride reduction of the lactone moiety.

  从(1R,5R,8R)-8-乙酰氧基-2-氧杂双环[3.3.5-deoxy-4a(R)-hydroxy-4a-carba-α-D-xylo-hexofuranose 23 和 4a(R)-hydroxy-2-amino-2,5-dideoxy-4a(R)-hydroxy-4a-carba-α-D-arabino-hexofuranose 1。该方法包括 OsO4 催化的二羟基化和区域选择性环氧化物开环，然后用硼氢化钙还原内酯分子。
• A Study on the Allylic Substitution of (1R,5R,8R)- and (1R,5R,8S)-8-Hydroxy-2-oxabicyclo[3.3.0]oct-6-en-3-one Derivatives − Preparation of (1S,2R,3R)-9-[2-Hydroxy-3-(2-hydroxyethyl)cyclopent-4-en-1-yl]-9H-adenine
  作者：Steen K. Johansen、Inge Lundt

  DOI：10.1002/1099-0690(200103)2001:6<1129::aid-ejoc1129>3.0.co;2-t

  日期：2001.3

  both C-6 and C-8 substituted products, thus limiting the synthetic use of the reaction with these nucleophiles. Additionally, Mitsunobu substitution of (1R,5R,8R)-8-hydroxy-2-oxabicyclo[3.3.0]oct-6-en-3-one (3) with 6-chloropurine, followed by reduction of the lactone moiety and treatment with liquid ammonia, gave the carbocyclic nucleoside (1S,2R,3R)-9-[2-hydroxy-3-(2-hydroxyethyl)cyclopent-4-en-1-yl]-9H-adenine

  钯催化的酰化（1 R，5 R，8 R）-和（1 R，5 R，8 S）-8-羟基-2-氧杂双环[3.3.0] oct-6-en-3-的取代已经使用许多C-和N-亲核试剂对它们进行了研究。在所有情况下，发现外切衍生物（8 R）比相应的内切衍生物（8 S）更具活性。）。当使用丙二酸二甲酯钠作为亲核试剂时，发现该反应产生良好的产率和单一产物。然而，当使用反应性较低的C-和N-亲核试剂时，反应给出了C-6和C-8取代产物的不可分离的混合物，因此限制了与这些亲核试剂的合成反应。另外，用6-氯嘌呤将（1 R，5 R，8 R）-8-羟基-2-氧杂双环[3.3.0] oct-6-en-3-one（3）的Mitsunobu取代，然后还原内酯部分并用液氨处理，得到碳环核苷（1 S，2 R，3 R）-9- [2-羟基-3-（2-羟乙基）环戊-4-en-1-基] -9 H-腺嘌呤（19），其可以被视为碳环核苷BCA的类似物。
• Modular, Well-Behaved Reversible Polymers from DNA-Based Monomers
  作者：Elizabeth A. Fogleman、Wayne C. Yount、Jun Xu、Stephen L. Craig

  DOI：10.1002/1521-3773(20021104)41:21<4026::aid-anie4026>3.0.co;2-e

  日期：2002.11.4

表征谱图