(1R,3R,5S)-endo-1,3-dimethyl-2,9-dioxabicyclo<3.3.1>nonane | 76740-34-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,3R,5S)-endo-1,3-dimethyl-2,9-dioxabicyclo<3.3.1>nonane
• 英文别名: (-)-(1R,3R,5S)-1,3-dimethyl-2,9-dioxabicyclo<3.3.1>nonane；(1R,3R,5S)-1,3-dimethyl-2,9-dioxabicyclo<3.3.1>nonane；(1R,3R,5S)-1,3-dimethyl-2,9-dioxabicyclo[3.3.1]nonane
• CAS: 76740-34-6
• 化学式: C₉H₁₆O₂
• 分子量: 156.225
• InChiKey: HNESZEUAUXADTQ-HRDYMLBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-(2-甲基-1,3-二氧杂烷-2-基)丁酸乙酯 在 Ra-Ni 盐酸 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 N-氯代丁二酰亚胺 、 lithium aluminium tetrahydride 、 二乙基甲氧基硼烷 、 盐酸羟胺 、 氢气 、 sodium acetate 、 硼酸 、 L-Selectride 、 碳酸氢钠 、 sodium carbonate 、 三乙胺 、 pyridinium chlorochromate 、 sodium iodide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丁酮 为溶剂， 反应 94.5h， 生成 (1R,3R,5S)-endo-1,3-dimethyl-2,9-dioxabicyclo<3.3.1>nonane
  参考文献：
  名称：

  On the scope of asymmetric nitrile oxide cycloadditions with Oppolzer's chiral sultam. Total syntheses of (+)-hepialone, (-)-(1R,3R,5S)-1,3-dimethyl-2,9-dioxabicyclo[3.3.1]nonane, and (-)-(1S)-7,7-dimethyl-6,8-dioxabicyclo[3.2.1]octane

  摘要：

  DOI：

  10.1021/jo00302a023

文献信息

• Synthesis of 4, 6-dialkyl-1,3-dioxins. Versatile intermidiates for the preparation of (E)-alkenones, anti,anti-1, 2, 3-triols and syn-1, 3-diols
  作者：Raymond L. Funk、Gary L. Bolton

  DOI：10.1016/s0040-4039(00)86663-0

  日期：1988.1

  The title compounds 4 are prepared from 4-alkyldioxins 2 via a metalation, alkylation sequence. The dialkyl dioxins 4 are thermally labile (providing enones) and undergo highly stereoselective hydroboration or hydrogenation reactions to provide anti, anti-1, 2, 3-triols and syn, 1, 3-diols, respectively. This methodology has been exploited in the synthesis of (±)-endo-1, 3-dimethyl-2,9-dioxabicyclo[3

  标题化合物4由4-烷基二恶英2经金属化，烷基化顺序制备。二烷基二恶英4是热不稳定的（提供烯酮），并经历高度立体选择性的硼氢化或氢化反应以分别提供抗，抗-1、2、3-三醇和syn，1、3-二醇。该方法已被用于合成（±）-endo-1、3-二甲基-2,9-二氧杂双环[3.3.1]壬烷。
• Optically active esters of 7-substituted 3,5-difunctionalized 6-heptenoic acids
  申请人：SAGAMI CHEMICAL RESEARCH CENTER

  公开号：EP0475627A1

  公开（公告）日：1992-03-18

  An optically active ester of formula (I): wherein:    R is a substituted or unsubstituted aromatic group, a substituted or unsubstituted heteroaromatic group or a substituted vinyl group;    Ar is a condensed aromatic group;    X¹ and Y¹ are not the same and each is a hydrogen atom or a hydroxyl group, or together represent an oxygen atom which forms a carbonyl group together with the carbon atom to which X¹ and Y¹ are attached; and    X² and Y² are not the same and each is a hydrogen atom or a hydroxyl group, or together represent an oxygen atom which forms a carbonyl group together with the carbon atom to which X² and Y² are attached, or an enantiomer thereof.

  化学式为（I）的光学活性酯，其中：R是取代或未取代的芳香基团，取代或未取代的杂环芳香基团或取代的乙烯基团；Ar是紧缩的芳香基团；X¹和Y¹不相同，每个都是氢原子或羟基，或者一起表示一个氧原子，该氧原子与X¹和Y¹连接的碳原子形成一个羰基基团；X²和Y²不相同，每个都是氢原子或羟基，或者一起表示一个氧原子，该氧原子与X²和Y²连接的碳原子形成一个羰基基团，或其对映异构体。
• Synthesis of isomeric 1,3-dimethyl-2,9-dioxabicyclo[3.3.1]nonanes and 1’-hydroxybrevicomin from ethyl 5-oxohexenoate ethyleneacetal through cyclopropanation of an ester group followed by oxidative opening of the three-membered ring
  作者：D. A. Astashko、O. G. Kulinkovich、V. I. Tyvorskii

  DOI：10.1134/s1070428006050125

  日期：2006.5

  Syntheses were performed of (+/-)-endo-1,3-dimethyl-2,9-dioxabicyclo[3.3.1]nonane and (+/-)-1'-hydroxyexo-brevicomin constituting racemic forms of the secretion components of pine weever (Hylobius abietis) and bark beetle of upland pines (Dendroctonus ponderosae) through cyclopropanation of the ester group of an available ethyl 5-oxohexanoate ethyleneacetal with the subsequent oxidative opening of the three-membered ring in the compound obtained.
• Stereospecific synthesis of exo- and endo-1,3-dimethyl-2,9-dioxabicyclo-[3.3.1]-nonane
  作者：Philip C.Bulman Page、Christopher M. Rayner、Ian O. Sutherland

  DOI：10.1016/s0040-4039(00)84843-1

  日期：1986.1
• Synthesis of endo-1,3-dimethyl-2,9-dioxa-bicyclo [3.3.1.] nonane
  作者：Peter Mohr、Christoph Tamm

  DOI：10.1016/s0040-4039(00)95737-x

  日期：1987.1