(3aα,6α,7aβ)-hexahydro-3,3,6-trimethyl-1(3H)-isobenzofuranone

• 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: (3aα,6α,7aβ)-hexahydro-3,3,6-trimethyl-1(3H)-isobenzofuranone
• 英文别名: (3aR,6R,7aR)-3,3,6-trimethylhexahydroisobenzofuran-1(3H)-one；(3aR,6R,7aR)-3,3,6-trimethyl-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1-one
• 化学式: C₁₁H₁₈O₂
• 分子量: 182.263
• InChiKey: YULJYTPERHRBQM-IWSPIJDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 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：

  (1R,2S,5R)-5-甲基-2-异丙基环己基甲酸 在 acetyl hypobromite 、 四溴化碳 、 silver(I) acetate 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 14.5h， 生成 (3aα,6α,7aβ)-hexahydro-3,3,6-trimethyl-1(3H)-isobenzofuranone
  参考文献：
  名称：

  Synthesis of Lactones via C–H Functionalization of Nonactivated C(sp³)–H Bonds

  摘要：

  An electron-deficient amide is utilized as a directing group to functionalize nonactivated C(sp(3))-H bonds through radical 1,5-hydrogen abstraction. The gamma-bromoamides formed are subsequently converted to gamma-lactones under mild conditions. The method described is not limited to tertiary and secondary positions but also allows functionalization of primary nonactivated sp(3)-hybridized positions in a one-pot sequence. In addition, the broad functional group tolerance renders this method suitable for the late-stage introduction of gamma-lactones into complex carbon frameworks.

  DOI：

  10.1021/acs.orglett.6b03371

文献信息

• Oxidative Cyclization of Unsaturated Ketene Dithioacetals with Ceric Ammonium Nitrate to Form Bicyclic Lactones
  作者：Barry B Snider、Bo Shi、Cheri A Quickley

  DOI：10.1016/s0040-4020(00)00857-7

  日期：2000.12

  Ceric ammonium nitrate oxidizes unsaturated ketene dithioacetals in wet MeCN to give cation radicals that cyclize to tri-substituted double bonds and styrenes by cation-like cyclizations leading to cyclic cation radicals that are transformed by further oxidation, hydrolysis and cyclization to bicyclic lactones in moderate to good yield. (C) 2000 Elsevier Science Ltd. All rights reserved.