(4R,5R)-4-ethyl-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolane | 82570-60-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,5R)-4-ethyl-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolane
• 英文别名: ((4R,5R)-5-ethyl-2,2-dimethyl-1,3-dioxolan-4-yl)methanol；[(4R,5R)-5-ethyl-2,2-dimethyl-1,3-dioxolan-4-yl]methanol
• CAS: 82570-60-3
• 化学式: C₈H₁₆O₃
• 分子量: 160.213
• InChiKey: QHUHMAOJQQHMFO-RNFRBKRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R,5R)-4-ethyl-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolane 在 咪唑 、 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 碘 、 sodium hydride 、 potassium carbonate 、 臭氧 、 silver nitrate 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 丙酮 、 苯 为溶剂， 反应 50.08h， 生成 (R)-1-(((1-bromopent-1-yn-3-yl)oxy)methyl)-4-methoxybenzene
  参考文献：
  名称：

  First total synthesis and structure confirmation of diacetylenic polyol (+)-oploxyne B

  摘要：

  The first total synthesis of the natural product (+)-oploxyne B is achieved. The synthesis has led to the confirmation of absolute stereochemistry of the natural product. The natural product displayed cytotoxic activity with IC50 values varying from 16 to 53 mu M in four cancer cell lines tested. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.08.020
• 作为产物：
  描述：

  (-)-2,3-O-亚异丙基-D-苏力糖醇 在 正丁基锂 作用下， 以 乙醚 为溶剂， 反应 4.25h， 生成 (4R,5R)-4-ethyl-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolane
  参考文献：
  名称：

  A novel carbon-carbon bond-forming reaction of triflates with copper(I)-catalyzed Grignard reagents. A new concise and enantiospecific synthesis of (+)-exo-brevicomin, (5R,6S)-(-)-6-acetoxy-5-hexadecanolide, and L-factor

  摘要：

  DOI：

  10.1021/jo00301a038

文献信息

• Formal Synthesis of (+)‐Laurencin by Gold(I)‐Catalyzed Intramolecular Dehydrative Alkoxylation
  作者：Megan L. Lanier、Hyeri Park、Paramita Mukherjee、Jacob C. Timmerman、Anthony A. Ribeiro、Ross A. Widenhoefer、Jiyong Hong

  DOI：10.1002/chem.201700499

  日期：2017.5.29

  8‐Membered cyclic ethers are found in a wide range of natural products; however, they are challenging synthetic targets due to enthalpic and entropic barriers. The gold(I)‐catalyzed intramolecular dehydrative alkoxylation of ω‐hydroxy allylic alcohols was explored to stereoselectively construct α,α′‐cis‐oxocenes and further applied in a formal synthesis of (+)‐laurencin. The gold(I)‐catalyzed intramolecular

  8-元环醚存在于多种天然产物中。然而，由于焓和熵的屏障，它们对合成目标具有挑战性。探索了金（I）催化的ω-羟基烯丙醇的分子内脱水烷氧基化反应以立体选择性地构建α，α'-顺式茂新烯烃，并进一步用于（+）-月桂素的形式合成中。金（I）催化的分子内脱水烷氧基化反应可能是合成包含高功能化8元环醚的分子构件和天然产物的另一种方法。
• KOTSUKI, HIYOSHIZO;KADOTA, ISAO;OCHI, MASAMITSU, J. ORG. CHEM., 55,(1990) N4, C. 4417-4422
  作者：KOTSUKI, HIYOSHIZO、KADOTA, ISAO、OCHI, MASAMITSU

  DOI：——

  日期：——
• [EN] ORGANIC COMPOUNDS<br/>[FR] COMPOSÉS ORGANIQUES
  申请人：BARRY CLIFTON

  公开号：WO2011087995A2

  公开（公告）日：2011-07-21

  This invention provides compounds which are useful in the treatment of mycobacterial infections, pharmaceutical compositions containing the compounds, processes for their preparation, and uses of the compounds in various medicinal applications, such as the treatment or prevention of mycobacterial infections, such as those caused by Mycobacterium tuberculosis, Mycobacterium bovis, Mycobacterium leprae, Mycobacterium africanum, Mycobacterium avium, Mycobacterium microti, or any mycobacterium that causes multi-drug resistant (MDR) TB or extensively resistant (XDR) TB, or any other mycobacterial species known to cause disease in humans; or the treatment or prevention of parasitic diseases, such as those caused by a parasite of the genus Trypanosoma, e.g. Trypanosoma cruzi or Trypanosoma brucei or a parasite of the genus Leishmania which causes visceral leishmaniasis or kala-azar, e.g., Leishmania donovani.
• A novel carbon-carbon bond-forming reaction of triflates with copper(I)-catalyzed Grignard reagents. A new concise and enantiospecific synthesis of (+)-exo-brevicomin, (5R,6S)-(-)-6-acetoxy-5-hexadecanolide, and L-factor
  作者：Hiyoshizo Kotsuki、Isao Kadota、Masamitsu Ochi

  DOI：10.1021/jo00301a038

  日期：1990.7
• First total synthesis and structure confirmation of diacetylenic polyol (+)-oploxyne B
  作者：P. Srihari、A. Sathish Reddy、J.S. Yadav、D. Yedlapudi、Shasi V. Kalivendi

  DOI：10.1016/j.tetlet.2013.08.020

  日期：2013.10

  The first total synthesis of the natural product (+)-oploxyne B is achieved. The synthesis has led to the confirmation of absolute stereochemistry of the natural product. The natural product displayed cytotoxic activity with IC50 values varying from 16 to 53 mu M in four cancer cell lines tested. (C) 2013 Elsevier Ltd. All rights reserved.