ethyl (2,3-dihydroxypropyl)carbamate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl (2,3-dihydroxypropyl)carbamate
• 英文别名: ethyl N-(2,3-dihydroxypropyl)carbamate
• 化学式: C₆H₁₃NO₄
• 分子量: 163.174
• InChiKey: POEIFGSNSQVNJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  78.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  叔丁基二甲基氯硅烷 、 ethyl (2,3-dihydroxypropyl)carbamate 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以84%的产率得到ethyl (3-((tert-butyldimethylsilyl)oxy)-2-hydroxypropyl)carbamate
  参考文献：
  名称：

  铜催化氨基醇氨基甲酸酯一锅法合成N-芳基恶唑烷酮

  摘要：

  已经开发出在氨基甲酸酯氨基甲酸酯的有效顺序分子内环化，然后在温和条件下与芳基碘化物进行铜催化的交叉偶联。该反应以高收率进行，并且可以耐受含有官能团（例如腈，酮，醚和卤素）的芳基碘化物。杂芳基碘化物和取代的氨基醇氨基甲酸酯也被很好地耐受。

  DOI：

  10.1021/ol502322c
• 作为产物：
  描述：

  在 potassium fluoride 、 双氧水 、 potassium hydrogencarbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 12.0h， 生成 ethyl (2,3-dihydroxypropyl)carbamate
  参考文献：
  名称：

  二烯基硅烷的不对称氨基羟基化。氨基环糖醇的有效途径

  摘要：

  甲硅烷基2,5-环己二烯的无尖锐的不对称氨基羟基化反应发生，具有完全的区域和非对映异构控制。还观察到高达68％ee的对映选择性。描述了该方法在氨基-环醇的相关实例的合成中的应用。

  DOI：

  10.1016/s0040-4039(97)00079-8

文献信息

• Copper-Catalyzed One-Pot Synthesis of <i>N</i>-Aryl Oxazolidinones from Amino Alcohol Carbamates
  作者：William Mahy、Pawel K. Plucinski、Christopher G. Frost

  DOI：10.1021/ol502322c

  日期：2014.10.3

  sequential intramolecular cyclization of amino alcohol carbamates followed by Cu-catalyzed cross-coupling with aryl iodides under mild conditions has been developed. The reaction occurred in good yields and tolerated aryl iodides containing functionalities such as nitriles, ketones, ethers, and halogens. Heteroaryl iodides and substituted amino alcohol carbamates were also well tolerated.

  已经开发出在氨基甲酸酯氨基甲酸酯的有效顺序分子内环化，然后在温和条件下与芳基碘化物进行铜催化的交叉偶联。该反应以高收率进行，并且可以耐受含有官能团（例如腈，酮，醚和卤素）的芳基碘化物。杂芳基碘化物和取代的氨基醇氨基甲酸酯也被很好地耐受。
• Photolabile arylsilyl group: application to the oxidation of C–Si bonds
  作者：Susen Werle、Frédéric Robert、Henri Bouas-Laurent、Yannick Landais

  DOI：10.1016/j.tetlet.2007.10.057

  日期：2007.12

  (2,6-Dimethoxyphenyl)-dimethylsilyl group constitutes a new orthogonal masked hydroxyl group. Protodesilylation of this arylsilane occurs under photochemical conditions in the presence of alcohols such as hexafluoroisopropanol (HFIP) or isopropanol. These mild and neutral conditions thus allowed the oxidation of organosilicon compounds such as β-hydroxysilanes that are known to be prone to Peterson

  （2，6-二甲氧基苯基）-二甲基甲硅烷基构成新的正交掩蔽的羟基。在光化学条件下，在醇如六氟异丙醇（HFIP）或异丙醇的存在下，这种芳基硅烷的原甲硅烷基化反应会发生。因此，这些温和和中性的条件允许氧化有机硅化合物，例如已知易于彼得森消除的β-羟基硅烷。
• Desymmetrization of Cyclohexadienylsilanes. Regio-, Diastereo-, and Enantioselective Access to Sugar Mimics
  作者：Rémy Angelaud、Odile Babot、Trevor Charvat、Yannick Landais

  DOI：10.1021/jo991225z

  日期：1999.12.1

  Desymmetrization of cyclohexadienylsilanes available from Birch reduction of the corresponding arylsilanes is efficiently carried out using Sharpless asymmetric dihydroxylation and aminohydroxylation. Complete diastereocontrol and reasonable enantiocontrol have been attained during the preparation of the desired diols. An excellent regiocontrol has also been observed during aminohydroxylation of dienylsilanol 6b. The resulting diol 8 and hydroxycarbamate 27 have then been elaborated further, offering a straightforward access to various types of cyclitols, aminocyclitols, carbasugars, as well as the antibiotic palitantine 4. The complete functionalization of the original arylsilanes 5 is thus typically achieved in fewer than eight steps with high stereoselectivities and excellent overall yield.
• FATTY ACID CYSTEAMINE CONJUGATES AND THEIR USE AS ACTIVATORS OF AUTOPHAGY
  申请人：Catabasis Pharmaceuticals, Inc.

  公开号：US20170258741A1

  公开（公告）日：2017-09-14

  The invention relates to (i) 6-membered heteroaryl substituted fatty acid cystamine conjugates, compositions thereof, methods of treating diseases involving dysregulation of autophagy, such as cystic fibrosis, idiopathic pulmonary fibrosis (IPF), a neurodegenerative disease, inflammatory disease, liver disease, muscle disease, infection and immune disease with this compound, or (ii) a method of treating idiopathic pulmonary fibrosis, mitochondrial diseases, Leigh Syndrome, Diabetes Mellitus and Deafness (DAD), Leber's hereditary optic neuropathy, Neuropathy-ataxia-retinis pigmentosa and ptosis (NARP), myoneurogenic gastrointestinal encephalopathy (MNG1E), myoclonic epilepsy with ragged red fibers (MERRF), or mitochondrial myopathy-encephalomy-opathy-lactic acidosis stroke like symptoms (MELAS), comprising administering to a patient the fatty acid cysteamine conjugate, (4Z, 7Z. 10Z, 13Z, 16Z, 19Z)—N-(2-mercaptoethyl) docosa-4,7,10,13,16,19-hexaenamide or (5Z, 8Z, 11Z, 14Z, 17Z)—N-(2-mercaptoethyl) icosa-5,8,11,14,17-pentaenamide.
• Copper Catalyzed Assembly of<i>N</i>-Aryloxazolidinones: Synthesis of Linezolid, Tedizolid, and Rivaroxaban
  作者：William Mahy、Jamie A. Leitch、Christopher G. Frost

  DOI：10.1002/ejoc.201600033

  日期：2016.3

  The total synthesis of oxazolidinone-based pharmaceuticals, linezolid, tedizolid and rivaroxaban is reported. They are synthesized using a recently reported copper-catalyzed one-pot cyclization and arylation as the key step to construct the N-aryloxazolidinone core. Active pharmaceutical ingredients (API) were synthesized from a common synthetic pool of a simple protected amino alcohol in 22 %, 61 %

  报道了基于恶唑烷酮的药物利奈唑胺、泰地唑胺和利伐沙班的全合成。它们是使用最近报道的铜催化一锅环化和芳基化合成的，作为构建 N-芳基恶唑烷酮核心的关键步骤。活性药物成分 (API) 由简单的受保护氨基醇的常见合成池合成，总合成产率分别为 22%、61% 和 40%。