3-[(4S,5R)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]propanal | 1007602-50-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-[(4S,5R)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]propanal
• CAS: 1007602-50-7
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: GXWHZVATIFHNCH-BDAKNGLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  3-[(4S,5R)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]propanal 、 N-甲氧基-N-甲基-2-(三苯基磷)乙酰胺N-甲氧基-N-甲基-2-(三苯基磷)乙酰胺 以 二氯甲烷 为溶剂， 反应 14.0h， 以13 mg的产率得到(Z)-N-methoxy-N-methyl-5-((4S,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)pent-2-enamide
  参考文献：
  名称：

  Total Synthesis of Aigialomycin D using a One-Pot Ketene Generation−Trapping−Aromatization Sequence

  摘要：

  The total synthesis of aigialomycin D, without the need for phenol protection, was carried out using the C-acylation of a keto-dioxinone dianion, a cascade sequence consisting of ketene generation, alcohol trapping and aromatization, and ring-closing metathesis.

  DOI：

  10.1021/ol901979x
• 作为产物：
  描述：

  ethyl 3-((4S,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)propanoate 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 3-[(4S,5R)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]propanal
  参考文献：
  名称：

  Total Synthesis of Aigialomycin D using a One-Pot Ketene Generation−Trapping−Aromatization Sequence

  摘要：

  The total synthesis of aigialomycin D, without the need for phenol protection, was carried out using the C-acylation of a keto-dioxinone dianion, a cascade sequence consisting of ketene generation, alcohol trapping and aromatization, and ring-closing metathesis.

  DOI：

  10.1021/ol901979x

文献信息

• Novel Macrocycles and Uses Thereof
  申请人：Danishefsky Samuel J

  公开号：US20080108694A1

  公开（公告）日：2008-05-08

  The present invention relates to compounds having the structure (and pharmaceutically acceptable derivatives thereof) wherein R o -R 4 , Z, X, A-B, D-E, G-J, and K-L are as defined herein, the synthesis thereof and the use of these compounds as therapeutic agents.
• Total Synthesis of Aigialomycin D using a One-Pot Ketene Generation−Trapping−Aromatization Sequence
  作者：Frederick Calo、Jeffery Richardson、Anthony G. M. Barrett

  DOI：10.1021/ol901979x

  日期：2009.11.5

  The total synthesis of aigialomycin D, without the need for phenol protection, was carried out using the C-acylation of a keto-dioxinone dianion, a cascade sequence consisting of ketene generation, alcohol trapping and aromatization, and ring-closing metathesis.