3-hydroxy-3-methyl-4,5,6,7-tetrahydroisobenzofuran-1(3H)-one | 115296-66-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异苯并呋喃
• 英文名称: 3-hydroxy-3-methyl-4,5,6,7-tetrahydroisobenzofuran-1(3H)-one
• 英文别名: Xyqgfifueiohsc-uhfffaoysa-；3-hydroxy-3-methyl-4,5,6,7-tetrahydro-2-benzofuran-1-one
• CAS: 115296-66-7
• 化学式: C₉H₁₂O₃
• 分子量: 168.192
• InChiKey: XYQGFIFUEIOHSC-UHFFFAOYSA-N

物化性质

• 沸点：
  375.0±30.0 °C(predicted)
• 密度：
  1.25±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  3-hydroxy-3-methyl-4,5,6,7-tetrahydroisobenzofuran-1(3H)-one 生成 7-fluoro-2-methyl-6-(1-methylidene-3-oxo-4,5,6,7-tetrahydroisoindol-2-yl)-4-prop-2-ynyl-1,4-benzoxazin-3-one
  参考文献：
  名称：

  SAJTO, KEHNDZI;SATO, DZYUNDZI;ISIKAVA, XISAO

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl 2-((trimethylsilyl)ethynyl)cyclohex-1-ene-1-carboxylate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 以88%的产率得到3-hydroxy-3-methyl-4,5,6,7-tetrahydroisobenzofuran-1(3H)-one
  参考文献：
  名称：

  烯炔酰胺到稠合吡啶酮：范围和限制

  摘要：

  在此，我们对从相应的烯炔酰胺合成环戊基和杂环稠合吡啶酮的范围和机制进行了研究。在仲胺的存在下，环化顺利进行，以 12-90% 的产率形成 5,6-双环吡啶酮。六元和更大环系统的烯炔酰胺环化失败。闭环反应对于仲胺而言本质上是催化性的，并且通过胺的顺序1,6-加成、亚胺中间体的6-外-三环闭环以及随后的仲胺的消除进行。计算表明，对于六元和更大的系统，烯炔和酰胺之间的共轭减少，从而为此类烯炔酰胺无法形成稠合吡啶酮提供了解释。

  DOI：

  10.1021/acs.joc.1c00688

文献信息

• Stereoselective One-Pot Method for the Introduction of an Amino Group to a Cyclohexane Ring. Preparation of the Octahydroisobenzofuro[7a,1-<i>d</i>]oxazole Ring System
  作者：Kenji Saito、Hideo Takagi、Makoto Yamamoto、Kazutoshi Yamada

  DOI：10.1055/s-1992-26353

  日期：——

  Stereoselective one-pot synthesis of octahydroisobenzofuro[7a,1-d]-oxazole-2,5-diones 7-14 via base-catalyzed addition-cyclization reaction of hydroxy lactones 4a-4d with various isocyanates 5a-5f is described. The ring system contains diastereoselectively regulated three contiguous asymmetric carbons.

  通过碱催化加成-环化反应，描述了羟基内酯4a-4d与各种异氰酸酯5a-5f的立体选择性一锅法合成八氢异苯并呋喃[7a,1-d]-恶唑-2,5-二酮7-14。该环系统包含立体选择性调控的三个连续不对称碳原子。
• A highly diastereoselective tandem Michael-Michael addition reaction in a rotameric ring system: steric acceleration due to conformation locking
  作者：Kenji Saito、Makoto Yamamoto、Kazutoshi Yamada、Hideo Takagi

  DOI：10.1016/s0040-4020(01)80175-7

  日期：1993.1

  A highly diastereoselective one-pot tandem Michael-Michael addition reaction developed in a rotamerically locked conformation is described. Reaction of isocyanates 8 - 13 with hydroxylactone 14 gave tandem Michael-Michael adducts 22 - 26 in good to excellent yields. The intermediate tricyclic oxazolidinones consisted of rotamer pairs 16 - 19, and the rotation barriers of some of these compounds were determined. The tandem addition reaction was highly accelerated by introducing conformation anchoring group X. A new versatile synthesis of octahydroacridines 27 - 29 using the tandem adducts is also described.
• Synthesis and stereochemical behavior of 1-aryloctahydroisobenzofuro[7a,1-d]oxazole ring system: new examples of isolable rotamers.
  作者：Kenji Saito、Makoto Yamamoto、Kazutoshi Yamada

  DOI：10.1016/s0040-4020(01)81284-9

  日期：1993.5

  Preparation and stereochemical behavior of new examples of isolable rotamers are described. Reaction of hydroxylactone 2 with isocyanates 3 - 11 gave the corresponding 12 - 20 in good yields. Among them, ortho di-substituted ones gave isolable rotamers. The behavior of ortho mono-substituted derivatives is also discussed.
• SAJTO, KEHNDZI;AKIXARA, KEHNDZI;XARA, UDZIO;ISIKAVA, XISAO;INABA, XIDEHO;+
  作者：SAJTO, KEHNDZI、AKIXARA, KEHNDZI、XARA, UDZIO、ISIKAVA, XISAO、INABA, XIDEHO、+

  DOI：——

  日期：——
• JPS6339859A
  申请人：——

  公开号：JPS6339859A

  公开（公告）日：1988-02-20

表征谱图