(R)-(+)-2,2,4-Trimethyl-4-<2-(benzyloxy)ethyl>-1,3-dioxolane | 170238-75-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-(+)-2,2,4-Trimethyl-4-<2-(benzyloxy)ethyl>-1,3-dioxolane
• 英文别名: (R)-2,2,4-trimethyl-4-[2'-(phenylmethoxy)ethyl]-1,3-dioxolane；(4R)-2,2,4-trimethyl-4-(2-phenylmethoxyethyl)-1,3-dioxolane
• CAS: 170238-75-2
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: KYEKENXMMCRYPU-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-(+)-2,2,4-Trimethyl-4-<2-(benzyloxy)ethyl>-1,3-dioxolane 在 硫酸 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以92%的产率得到(R)-2-methyl-4-(phenylmethoxy)butane-1,2-diol
  参考文献：
  名称：

  真菌颜料。六。柠檬酸合成(1S,3S)-和(1R,3R)-Austrocortilutein和(1S,3S)-Austrocortirubin

  摘要：

  天然存在的四氢蒽醌 (1S,3S)-austrocortilutein (1) 首次通过功能化丁二烯衍生物 (8) 和手性 1,3-二羟基-1,2,3,4- 之间的 Diels-Alder 环加成以对映体纯形式合成tetrahydro-5,8-naphthoquinone (9)，后者衍生自 (R)-柠苹果酸 (3)。naturalproducts (1S,3S)-austrocortirubin(2) 和(1R,3R)-austrocortilutein(5) 也是第一次使用相同的策略制备。

  DOI：

  10.1071/ch99091
• 作为产物：
  描述：

  (R)-dimethyl 2-hydroxy-2-methylsuccinate 在 lithium aluminium tetrahydride 、 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 反应 66.0h， 生成 (R)-(+)-2,2,4-Trimethyl-4-<2-(benzyloxy)ethyl>-1,3-dioxolane
  参考文献：
  名称：

  真菌颜料。六。柠檬酸合成(1S,3S)-和(1R,3R)-Austrocortilutein和(1S,3S)-Austrocortirubin

  摘要：

  天然存在的四氢蒽醌 (1S,3S)-austrocortilutein (1) 首次通过功能化丁二烯衍生物 (8) 和手性 1,3-二羟基-1,2,3,4- 之间的 Diels-Alder 环加成以对映体纯形式合成tetrahydro-5,8-naphthoquinone (9)，后者衍生自 (R)-柠苹果酸 (3)。naturalproducts (1S,3S)-austrocortirubin(2) 和(1R,3R)-austrocortilutein(5) 也是第一次使用相同的策略制备。

  DOI：

  10.1071/ch99091

文献信息

• Enantioselective Hydrolysis of Functionalized 2,2-Disubstituted Oxiranes with Bacterial Epoxide Hydrolases
  作者：Andreas Steinreiber、Ingrid Osprian、Sandra F. Mayer、Romano V. A. Orru、Kurt Faber

  DOI：10.1002/1099-0690(200011)2000:22<3703::aid-ejoc3703>3.0.co;2-3

  日期：2000.11

  ether-oxygen to the stereogenic quaternary carbon center of the oxirane ring had a profound influence on the enantioselectivity, and several oxiranes were resolved with good to excellent selectivities. The enantiomerically enriched epoxides and vicinal diols thus obtained contain a useful “synthetic handle” in their side chain, which allows their use as building blocks in asymmetric synthesis.

  使用 11 种细菌菌株的环氧化物水解酶活性研究了带有各种氧官能团的 2,2-二取代环氧乙烷的生物水解。结果表明，活性和选择性强烈依赖于底物结构和生物催化剂。尽管具有游离羟基的底物没有被转化，但它们的类似物，被保护为醚，被广泛接受。这使得通过根据尺寸和极性正确选择醚组，可以方便地调制对映射性。发现醚-氧与环氧乙烷环的立体四元碳中心的距离对对映选择性有深远的影响，并且几种环氧乙烷以良好到极好的选择性分离。
• Enantioselective Synthesis of 2-Methyl-2-hydroxy-.gamma.-butyrolactone and Its Application in the Asymmetric Synthesis of Frontalin and Mevalonolactone
  作者：Franklin A. Davis、G. Venkat Reddy、Bang-Chi Chen、Anil Kumar、M. Serajul Haque

  DOI：10.1021/jo00124a030

  日期：1995.9

  The asymmetric hydroxylation of the enolates of fully substituted acyclic ester 8 and lactone 10 with (camphorylsulfonyl)oxaziridines 1a-c was studied. The stereoselectivities of the tertiary alpha-hydroxy carbonyl products were highly dependent on the enolate structure, the oxidizing reagents, and the reaction conditions. While high diastereoselectivity (up to 94%) was obtained for enolates of fully substituted menthol ester 8 with substoichiometric amounts of oxaziridine 1a, the yields were unsatisfactory. On the other hand, the enantioselective alpha-hydroxylation of the sodium enolate of 2-methyl-gamma-butyrolactone (10) with [(8,8-dimethoxycamphoryl)sulfonyl]oxaziridine (1c) afforded alpha-hydroxy lactone 11a in 70% yield and 84% ee. The enantiomeric excess was improved to > 93% ee by crystallization of the corresponding benzoyl ester 11c. The utility of both enantiomers of 11c were demonstrated in the formal asymmetric syntheses of the pheromone, (1S,5R)-(-)-frontalin (13) and in the asymmetric synthesis of (R)-(-)-mevalonolactone (20).