((1S,5R,8R)-1,5-Dimethyl-7-oxo-6-oxa-bicyclo[3.2.1]oct-8-yl)-acetic acid | 179465-48-6

• 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: ((1S,5R,8R)-1,5-Dimethyl-7-oxo-6-oxa-bicyclo[3.2.1]oct-8-yl)-acetic acid
• 英文别名: 2-[(1S,5R,8R)-1,5-dimethyl-7-oxo-6-oxabicyclo[3.2.1]octan-8-yl]acetic acid
• CAS: 179465-48-6
• 化学式: C₁₁H₁₆O₄
• 分子量: 212.246
• InChiKey: UMGXPONAYMEJBA-PPKCKEKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ((1S,5R,8R)-1,5-Dimethyl-7-oxo-6-oxa-bicyclo[3.2.1]oct-8-yl)-acetic acid 在 palladium on activated charcoal copper(l) iodide 、 LiAlH(O-t-C₃H₉)3 、 氢气 作用下， 以 高氯酸 、 乙醚 、 溶剂黄146 为溶剂， 生成 (+/-)-9,10-Secoabieta-8,11,13-trien-18,10-olide
  参考文献：
  名称：

  Chakraborti, Asit K.; Ghatak, Usha Ranjan, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1987, vol. 26, p. 295 - 296

  摘要：

  DOI：
• 作为产物：
  描述：

  (1S,5R,8R)-8-Benzyl-1,5-dimethyl-6-oxa-bicyclo[3.2.1]octan-7-one 在 sodium periodate 、 顺-双(2,2'-二吡啶基)二氯化钌(II)二水合物 作用下， 以 水 、 乙腈 为溶剂， 生成 ((1S,5R,8R)-1,5-Dimethyl-7-oxo-6-oxa-bicyclo[3.2.1]oct-8-yl)-acetic acid
  参考文献：
  名称：

  Chakraborti, Asit K.; Banik, Bimal K.; Ghatak, Usha Ranjan, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1984, vol. 23, # 4, p. 291 - 292

  摘要：

  DOI：

文献信息

• Alkali metal-liquid ammonia reduction of γ-lactones to diols and cyclic hemiacetals: stereochemical influence by the neighbouring group on the nature
  作者：Asit K. Chkraborty、Bijali Saha、Chhanda Ray、Usha Ranjan Ghatak

  DOI：10.1016/s0040-4020(01)90319-9

  日期：——

  Lithium or sodium-liquid aimmonia reduction of 3-hydroxy-1,3-dimethylcyclohexane-1,3-carbolactones (, () and () with or without a C-2 equatorial substituent gives the respective diols (), () and (), whereas the lactones () and (), having a C-2 axial substituent produce the respective cyclic hemiacetals () and () as the sole products. A possible mechanism has been suggested for rationalisation of these

  锂或钠-液体阿莫尼亚胺还原带有或不带有C-2赤道取代基的3-羟基-1,3-二甲基环己烷-1,3-碳内酯（，（）和（））分别得到二元醇（），（）和（），而具有C-2轴向取代基的内酯（）和（）则分别产生各自的环状半缩醛（）和（），为合理地解释这些结果提出了一种可能的机理。
• Asymmetric Total Synthesis of the Caribbean Fruit Fly Pheromone (+)-Epianastrephin
  作者：Arthur G. Schultz、Steven J. Kirincich

  DOI：10.1021/jo960568j

  日期：1996.1.1

  An asymmetric total synthesis of (+)-epianastrephin (1) from the chiral benzamide 2 (15 steps, 9.5% overall yield) is described. Birch reduction-alkylation of 2 with methyl iodide gave 3 in 91% yield as a single diastereomer. Cyclohexadiene 3 was converted to olefinic carboxylic acid 6b, and a tandem iodolactonization-radical reduction sequence provided lactone 8 with three contiguous stereogenic centers. Chiral HPLC comparison of diol 12b, the immediate precursor to (+)epianastrephin (1), with 12b prepared from racemic epianastrephin demonstrated that 1 had been prepared with > 98% ee.
• Extension of an Improved Procedure for the Ruthenium Tetroxide-Catalyzed Degradation of Aromatic Rings: A Highly Efficient and Stereocontrolled Synthesis of Functionalized Bridged-Ring and Carbocyclic Esters
  作者：Asit K. Chakraborti、Usha Ranjan Ghatak

  DOI：10.1055/s-1983-30498

  日期：——