2,2-diethyl-1,3-dioxolan-4-one | 162518-30-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2-diethyl-1,3-dioxolan-4-one
• 英文别名: 2,2-Diethyl-1,3-dioxolan-4-one
• CAS: 162518-30-1
• 化学式: C₇H₁₂O₃
• 分子量: 144.17
• InChiKey: YHEQXUOMOFREPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2-diethyl-1,3-dioxolan-4-one 、 (2R,4aR,6S,8S,8aR)-6,8-Bis-benzyloxy-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-7-one 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以66%的产率得到
  参考文献：
  名称：

  Synthesis of a peracetylated stereoisomer of De Rosa's calditol: Some questions about the correctness of the original structure assigned to this natural product

  摘要：

  Comparison of the C-13 nmr spectrum of the nonacetate of a synthetic stereoisomer of calditol with that of the nonacetate of the natural product, combined with a comparison of the C-13 nmr spectrum of the peracetate of a hexitol derived from calditol with all known peracetates of open chain hexitols, invalidates the originally proposed structure.

  DOI：

  10.1016/0040-4039(94)02388-r
• 作为产物：
  描述：

  羟基乙酸 、 3-戊酮 以76%的产率得到2,2-diethyl-1,3-dioxolan-4-one
  参考文献：
  名称：

  Two-step stereoselective conversion of 5-monosubstituted 1,3-dioxolan-4-ones into selectively protected 2,3-erythro-1,2,3-triols. A route to polyhydroxylated molecules

  摘要：

  5-Monosubstituted 1,3-dioxolan-4-one 1 are stereoselectively converted into selectively protected 2,3-erythro-1,2,9-triols 3 via Tebbe methylenation, followed by hydroboration-oxidation.

  DOI：

  10.1016/s0040-4039(00)77164-4

文献信息

• Asymmetric Total Synthesis of (+)-Cannabisativine
  作者：Jeffrey T. Kuethe、Daniel L. Comins

  DOI：10.1021/jo049724+

  日期：2004.8.1

  configuration. Luche reduction of ketone 16 afforded diol 17 in high yield (96%) and excellent diastereoselectivity. The Mukaiyama−Michael reaction of pyridones 27a/b with O-silyl ketene acetal 32 gave phenyl selenyl ketones 33a/b with complete stereoselectivity. Elimination of cis-β-hydroxyselenides 34 and 35 effected the regiocontrolled preparation of tetrahydropyridine derivative 29. Several approaches

  天然（+）-大麻二烯1的不对称总合成以19个步骤完成，总收率为7％。从手性1-酰基吡啶鎓盐10开始，分12步制备具有高度立体控制的关键合成中间体29。在吡啶鎓盐10中加入烯醇锌11可得到二氢吡啶酮12，其含有两个具有正确绝对构型的连续的立体中心。Luche还原酮16可获得高收率（96％）和出色的非对映选择性的二醇17。吡啶酮27a / b与O的Mukaiyama-Michael反应-甲硅烷基烯酮缩醛32得到完全立体选择性的苯基硒烯基酮33a / b。消除顺式-β-羟基硒化物34和35影响了四氢吡啶衍生物29的区域控制制备。研究了13位环大环封闭的几种方法，最终导致具有高度立体控制的目标化合物的不对称合成的完成。
• Diastereoselective Addition of Prochiral Metallo Enolates to Chiral 1-Acylpyridinium Salts
  作者：Daniel L. Comins、Jeffrey T. Kuethe、Hao Hong、Frederick J. Lakner、Thomas E. Concolino、Arnold L. Rheingold

  DOI：10.1021/ja990024+

  日期：1999.3.1
• Two-step stereoselective conversion of 5-monosubstituted 1,3-dioxolan-4-ones into selectively protected 2,3-erythro-1,2,3-triols. A route to polyhydroxylated molecules
  作者：Edouard Untersteller、Yan Chao Xin、Pierre Sinaÿ

  DOI：10.1016/s0040-4039(00)77164-4

  日期：1994.4

  5-Monosubstituted 1,3-dioxolan-4-one 1 are stereoselectively converted into selectively protected 2,3-erythro-1,2,9-triols 3 via Tebbe methylenation, followed by hydroboration-oxidation.
• Synthesis of a peracetylated stereoisomer of De Rosa's calditol: Some questions about the correctness of the original structure assigned to this natural product
  作者：Antony J. Fairbanks、Pierre Sinaỹ

  DOI：10.1016/0040-4039(94)02388-r

  日期：1995.2

  Comparison of the C-13 nmr spectrum of the nonacetate of a synthetic stereoisomer of calditol with that of the nonacetate of the natural product, combined with a comparison of the C-13 nmr spectrum of the peracetate of a hexitol derived from calditol with all known peracetates of open chain hexitols, invalidates the originally proposed structure.