5-hydroxy-4,5-dihydroisobenzofuran | 99758-16-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 5-hydroxy-4,5-dihydroisobenzofuran
• 英文别名: 4,5-dihydroisobenzofuran-5-ol；4,5-Dihydro-2-benzofuran-5-ol
• CAS: 99758-16-4
• 化学式: C₈H₈O₂
• 分子量: 136.15
• InChiKey: LWSMICHILFIXPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  33.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-hydroxy-4,5-dihydroisobenzofuran 在 sodium hydride 、 对甲苯磺酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 lithium chloride 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.25h， 生成 邻苯二甲醛
  参考文献：
  名称：

  有效合成4-取代的邻苯二甲醛类似物：迈向新的结构单元

  摘要：

  4-甲氧基邻-phthalaldehyde和4-羟基邻-phthalaldehyde是各种胺的荧光分析和复杂的分子结构的阐述潜在有用的分子。然而，文献通常以非常低的产率（低于5％）描述了它们的合成，这主要是由于最后的氧化步骤效率低下。在本文中，我们报告了由于不稳定关键中间体4，5-二氢异苯并呋喃-5-醇的保护步骤而可靠地合成了4个取代的邻苯二甲醛类似物，总产率为51％。还研究了氧化和脱保护步骤，以提供这两种二醛化合物的有效利用，这可能会增加它们的未来应用。

  DOI：

  10.3762/bjoc.15.67
• 作为产物：
  描述：

  2-((prop-2-yn-1-yloxy)methyl)furan 在 potassium tert-butylate 作用下， 以 水 、 叔丁醇 为溶剂， 以75 %的产率得到5-hydroxy-4,5-dihydroisobenzofuran
  参考文献：
  名称：

  通过路易斯酸催化的艾伦酮分子内迈克尔加成制备七元碳环

  摘要：

  报道了一种通过采用路易斯酸催化联烯酮分子内迈克尔加成来构建七元碳环的简单策略。它提供了合成重要的含有七元碳环的呋喃稠合双环或三环骨架的原子经济途径，这些骨架广泛存在于具有各种生物活性的天然产物中。许多带有不同官能团的七元碳环多环骨架以良好到优异的产率制备。此外，Caribenol A 和 Frondosin B 关键骨架的构建也证明了该策略的应用潜力。

  DOI：

  10.1021/acs.orglett.3c01732

文献信息

• Alternative synthetic approaches to (±)-euryfuran via the furan ring transfer reaction
  作者：Yoskiyasu Baba、Toshihiro Sakamoto、Seizo Soejima、Ken Kanematsu

  DOI：10.1016/s0040-4020(01)85635-0

  日期：1994.1

  effective synthetic approaches to (±)-euryfuran 1 are described. One synthetic route makes use of sequential furan ring transfer reaction type I and type III as key steps followed by Eschenmoser-type [3,3]sigmatropic rearrangement, and another route proceeded through furan ring transfer reaction type I and annulation with ethyl vinyl ketone subsequently.

  描述了两种有效的合成方法（±）-euryfuran 1。一种合成路线是使用顺序的I型和III型呋喃环转移反应作为关键步骤，然后进行Eschenmoser型[3,3]σ重排，另一种途径是通过I型呋喃环转移反应并随后与乙基乙烯基酮环化进行。 。
• Novel ring transfer reaction of furans via intramolecular Diels-Alder reaction of allene intermediate: a new double annulation reaction
  作者：Kenji Hayakawa、Yasuchika Yamaguchi、Ken Kanematsu

  DOI：10.1016/s0040-4039(00)98138-3

  日期：1985.1

  A novel ring tansfer reaction of furans to fused furans by tandem intramolecular Diels-Alder reaction and base-catalyzed ring-opening of the adducts has been developed.

  通过串联分子内Diels-Alder反应和加合物的碱催化开环，已经开发了呋喃向稠合呋喃的新型环转移反应。
• An Unusual Synthesis of Phthalaldehyde
  作者：Ernest Wenkert、Haripada Khatuya

  DOI：10.1080/00397919908086247

  日期：1999.7

  Abstract A variety of oxidizing agents convert 5-hydroxy-4,5-dihydroisobenzo-furan into phthalaldehyde. Other oxidizing agents produce both phthalaldehyde and its 4-hydroxy derivative.

  摘要 多种氧化剂可将 5-羟​​基-4,5-二氢异苯并呋喃转化为苯二醛。其他氧化剂会产生苯二醛及其 4-羟基衍生物。
• Intramolecular Diels−Alder Reaction of Furans with Allenyl Ethers Followed by Sulfur and Silicon Atom-Containing Group Rearrangement
  作者：Hsien-Jen Wu、Chia-Hui Yen、Chi-Te Chuang

  DOI：10.1021/jo980240l

  日期：1998.7.1

  The intramolecular Diels-Alder reactions of a furandiene with an allenyl ether dienophile followed by the alkylthio, alkylsulfinyl, alkylsulfonyl, and trimethylsilyl group rearrangements are reported. Refluxing the propargyl ether 3 with t-BuOK in t-BuOH at 85 degrees C gave the 1,4-rearrangement product 4 exclusively. The alkylthio group 1,4-rearrangement may proceed intramolecularly via the tight; ion pairs. Refluxing the 5-(alkylsulfinyl)-2-furfuryl propargyl ethers 9a-e and the 5-(alkylsulfonyl)-2-furfuryl propargyl ethers 19a-e under the same reaction conditions gave the alkylsulfinyl group and the alkylsulfonyl group 1,2-rearrangement products 10a-e and 20a-e, respectively. No detectable amount of the corresponding 1,4-rearrangement products 11a-e and 21a-e was obtained. In the cases of 9b and 19b, which possess two furfurylic hydrogen atoms, no detectable amount of the furan ring-transfer reaction products was obtained. Refluxing the 5-(trimethylsilyl)-2-furfuryl propargyl ethers 25a-d with t-BuOK in t-BuOH at 85 degrees C for 10 h gave the trimethylsilyl group 1,2-rearrangement products 26a-d and Brook rearrangement products 27a-d. The reaction mechanisms for these novel intramolecular Diels-Alder reactions are discussed. In the case of 37, which possesses two furfurylic hydrogen atoms, compound 38 was obtained via an intramolecular Diels-Alder reaction followed by the furan ring-transfer reaction and Brook rearrangement.
• Daisy Chain Assembly Formed from a Cucurbit[6]uril Derivative
  作者：Liping Cao、Lyle Isaacs

  DOI：10.1021/ol3011425

  日期：2012.6.15

  The building block synthesis of a derivative of CB[6] that bears a reactive propargyloxy group and its functionalization by click chemistry to yield 1 which contains a covalently attached isobutylammonium group is presented. Compound 1 undergoes self-assembly to yield a cyclic [c2] daisy chain assembly (1(2)) in water. The behavior of 1(2) in response to various stimuli (e.g., guests and CB[n] receptors) is described.