(4R,5S)-5-decyl-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde | 949463-64-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,5S)-5-decyl-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde
• CAS: 949463-64-3
• 化学式: C₁₆H₃₀O₃
• 分子量: 270.412
• InChiKey: XQTLFJPPOIBDBB-GJZGRUSLSA-N

物化性质

• 沸点：
  344.7±27.0 °C(predicted)
• 密度：
  0.947±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  19
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 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：

  (4R,5S)-5-decyl-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde 在 二异丁基氢化铝 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 14.0h， 生成 (4S,5S,Z)-4,5-(isopropylidenedioxy)pentadec-2-en-1-ol
  参考文献：
  名称：

  Diastereoselective synthesis of (+)-nephrosterinic acid and (+)-protolichesterinic acid

  摘要：

  A diastereoselective synthesis of (+)-nephrosterinic acid and (+)-protolichesterinic acid, common members of the paraconic acids is described. The synthesis is based on a diastereoselective orthoester Johnson-Claisen rearrangement of a (Z)-allyl alcohol with a vicinal dioxolane moiety as key steps. The synthesis is completed in 10 steps and with overall yields of 15.9% for (+)-nephrosterinic acid and 16.4% for (+)-protolichesterinic acid. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.12.012
• 作为产物：
  描述：

  ((4R,5S)-5-Decyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol 在 草酰氯 、 potassium carbonate 、 二甲基亚砜 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (4R,5S)-5-decyl-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde
  参考文献：
  名称：

  手性环氧醇的合成：（+）-异戊二烯的合成

  摘要：

  （2R，3S）-1,2-环氧醇1，（2S，3S）-2,3-环氧醇2和（2S，3S）-1,2-环氧醇3由易于获得的（-）制备-2-脱氧-D-核糖。使用环氧醇3b作为手性合成子，（+）- disparlure，合成了吉普赛蛾的信息素，Porthetria dispar（L.）。

  DOI：

  10.1016/s0040-4039(00)92629-7

文献信息

• Total Syntheses of Schulzeines B and C
  作者：Mukund K. Gurjar、Chinmoy Pramanik、Debabrata Bhattasali、C. V. Ramana、Debendra K. Mohapatra

  DOI：10.1021/jo070560h

  日期：2007.8.1

  Schulzeines B (2) and C (3) were synthesized by a convergent strategy using epimeric tricyclic lactam building blocks, 4 and 5, and the C28 fatty acid side chain 6. Syntheses of tricyclic lactams (4/5) were achieved by Bischler-Napieralski reaction. Sharpless asymmetric dihy-droxylation and BINAL-H-mediated asymmetric reduction of an enone was employed to prepare the key fatty acid side chain 6. The spectral as well as analytical data of 2 and 3 were in good agreement with the reported data for the natural products, thus confirming their assigned structures.
• Diastereoselective synthesis of (+)-nephrosterinic acid and (+)-protolichesterinic acid
  作者：Rodney A. Fernandes、Mahesh B. Halle、Asim K. Chowdhury、Arun B. Ingle

  DOI：10.1016/j.tetasy.2011.12.012

  日期：2012.1

  A diastereoselective synthesis of (+)-nephrosterinic acid and (+)-protolichesterinic acid, common members of the paraconic acids is described. The synthesis is based on a diastereoselective orthoester Johnson-Claisen rearrangement of a (Z)-allyl alcohol with a vicinal dioxolane moiety as key steps. The synthesis is completed in 10 steps and with overall yields of 15.9% for (+)-nephrosterinic acid and 16.4% for (+)-protolichesterinic acid. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis of chiral epoxy alcohols: synthesis of (+)-disparlure
  作者：Suk-Ku Kang、Yun-Sik Kim、Jong-Suk Lim、Kun-Soo Kim、Sung-Gyu Kim

  DOI：10.1016/s0040-4039(00)92629-7

  日期：1991.1

  (2R,3S)-1,2-Epoxy alcohols 1, (2S,3S)-2,3-epoxy alcohols 2, and (2S,3S)-1,2-epoxy alcohols 3 were prepared from readily available (−)-2-deoxy-D-ribose. Using epoxy alcohol 3b as a chiral synthon, (+)-disparlure, the pheromone of the gypsy moth, Porthetria dispar(L.), was synthesized.

  （2R，3S）-1,2-环氧醇1，（2S，3S）-2,3-环氧醇2和（2S，3S）-1,2-环氧醇3由易于获得的（-）制备-2-脱氧-D-核糖。使用环氧醇3b作为手性合成子，（+）- disparlure，合成了吉普赛蛾的信息素，Porthetria dispar（L.）。