(4S,5S)-5-(iodomethyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylic acid | 872831-85-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S,5S)-5-(iodomethyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylic acid
• CAS: 872831-85-1
• 化学式: C₇H₁₁IO₄
• 分子量: 286.066
• InChiKey: HQPJKOMUZLPOFM-UHNVWZDZSA-N

物化性质

• 熔点：
  97 °C
• 沸点：
  347.5±37.0 °C(Predicted)
• 密度：
  1.772±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 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：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S,5S)-5-(iodomethyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylic acid 在 偶氮二异丁腈 、 三正丁基氢锡 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 、 xylene 为溶剂， 反应 28.0h， 生成 6-(2,2,5-trimethyl[1,3]dioxolane-4-carbonyl)-6,7,8,9-tetrahydro-5H-1,3-dioxa-6-aza-cyclohepta[f]indene-9-carbonitrile
  参考文献：
  名称：

  Asymmetric Total Synthesis of the 1-epi-Aglycon of the Cripowellins A and B

  摘要：

  [GRAPHICS]The unusual [5.3.2]-bicyclic structure of the insecticidal Amaryllidaceae alkaloids cripowellin A (1) and B (2) has been synthesized for the first time via a sequence of Sharpless dihydroxylation, ring-closing metathesis, and intramolecular Heck reaction. The asymmetric synthesis of the 1-epiaglycon 82 proceeds with virtually complete diastereo- and enantioselectivity (de, ee >= 98%) in 13 steps and an overall yield of 5.6%. In addition, three alternative approaches toward the aglycon 3 are also described focusing on (1) the alkylation of the 2-benzazepinedithianes 35 and 36 with the electrophile 11, (2) a radical cyclization of the precursor (R/S,S,S)-39, and (3) an intramolecular arylation reaction of the aryl ketone 47.

  DOI：

  10.1021/jo0518093
• 作为产物：
  描述：

  methyl (4S,5S)-5-(iodomethyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以95%的产率得到(4S,5S)-5-(iodomethyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylic acid
  参考文献：
  名称：

  Asymmetric Total Synthesis of the 1-epi-Aglycon of the Cripowellins A and B

  摘要：

  [GRAPHICS]The unusual [5.3.2]-bicyclic structure of the insecticidal Amaryllidaceae alkaloids cripowellin A (1) and B (2) has been synthesized for the first time via a sequence of Sharpless dihydroxylation, ring-closing metathesis, and intramolecular Heck reaction. The asymmetric synthesis of the 1-epiaglycon 82 proceeds with virtually complete diastereo- and enantioselectivity (de, ee >= 98%) in 13 steps and an overall yield of 5.6%. In addition, three alternative approaches toward the aglycon 3 are also described focusing on (1) the alkylation of the 2-benzazepinedithianes 35 and 36 with the electrophile 11, (2) a radical cyclization of the precursor (R/S,S,S)-39, and (3) an intramolecular arylation reaction of the aryl ketone 47.

  DOI：

  10.1021/jo0518093