(S)-2,2-dimethyl-4-methoxycarbonyl-1,3-oxazolidine | 174840-02-9

• 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: (S)-2,2-dimethyl-4-methoxycarbonyl-1,3-oxazolidine
• 英文别名: (S)-methyl 2,2-dimethyloxazolidine-4-carboxylate；methyl (4S)-2,2-dimethyl-1,3-oxazolidine-4-carboxylate
• CAS: 174840-02-9
• 化学式: C₇H₁₃NO₃
• 分子量: 159.185
• InChiKey: XFUHHBPJJIJGDN-YFKPBYRVSA-N

物化性质

• 沸点：
  195.7±35.0 °C(Predicted)
• 密度：
  1.048±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  11
• 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：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2,2-dimethyl-4-methoxycarbonyl-1,3-oxazolidine 在 二异丁基氢化铝 、 potassium carbonate 、 N,N-二异丙基乙胺 、 sodium iodide 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 6.0h， 生成 N-allyl-N-isopropyl-L-serine methyl ester
  参考文献：
  名称：

  IOOC Route to Substituted Chiral Pyrrolidines. Potential Glycosidase Inhibitors

  摘要：

  Branched-chain five-membered ring aza-sugar analogues, synthesized from amino acids by an intramolecular oxime-olefin cycloaddition reaction, the IOOC route, were found to be selective glycosidase inhibitors. The derivative 2,4(S)-di(hydroxymethyl)-3(S)-aminopyrrolidine, obtained from D-serine, was about 1 order of potency more active than its enantiomer obtained from L-serine.

  DOI：

  10.1021/jo9815094
• 作为产物：
  描述：

  (S)-3-苄基-4-甲基-2,2-二甲基氧氮杂环-3,40二羧酸酯 在 Rh/Al₂O₃ 氢气 作用下， 以 乙醚 为溶剂， 反应 18.0h， 以84%的产率得到(S)-2,2-dimethyl-4-methoxycarbonyl-1,3-oxazolidine
  参考文献：
  名称：

  IOOC Route to Substituted Chiral Pyrrolidines. Potential Glycosidase Inhibitors

  摘要：

  Branched-chain five-membered ring aza-sugar analogues, synthesized from amino acids by an intramolecular oxime-olefin cycloaddition reaction, the IOOC route, were found to be selective glycosidase inhibitors. The derivative 2,4(S)-di(hydroxymethyl)-3(S)-aminopyrrolidine, obtained from D-serine, was about 1 order of potency more active than its enantiomer obtained from L-serine.

  DOI：

  10.1021/jo9815094

文献信息

• Chiral ligands containing heteroatoms. 14. 1,3-oxazolidinyl methanols as chiral catalysts in the enantioselective addition of diethylzinc to aldehydes
  作者：Massimo Falorni、Cristina Collu、Sandra Conti、Giampaolo Giacomelli

  DOI：10.1016/0957-4166(95)00448-3

  日期：1996.1

  3-oxazolidin-4-yl)-methanol and (4S,5R)-diphenyl-(2,2-dimethyl-5-methyl-1,3-oxazolidin-4-yl)-methanol were prepared in good yields. The use of these compounds as very efficient chiral catalysts for the enantioselective addition of diethylzinc to aldehydes is described. This paper reports the first example of the use of oxazolidine methanols in asymmetric synthesis.

  从左旋丝氨酸和左旋苏氨酸开始，（S）-二苯基-（2,2-二甲基-1,3-恶唑烷丁-4-基）-甲醇和（4 S，5 R）-二苯基-（2,2以高收率制备了-二甲基-5-甲基-1，3-恶唑烷丁-4-基）-甲醇。描述了这些化合物作为非常有效的手性催化剂用于将二乙基锌对映体选择性地加成到醛中的用途。本文报道了在不对称合成中使用恶唑烷甲醇的第一个实例。
• 10.1016/j.bmcl.2024.129792
  作者：Yasuda, Tomokazu、Ueura, Daiki、Nakagomi, Madoka、Hanashima, Shinya、Peter Slotte、Murata, Michio

  DOI：10.1016/j.bmcl.2024.129792

  日期：——

  Ceramide 1-phosphate (C1P) is a lipid mediator that specifically binds and activates cytosolic phospholipase Aα (cPLAα). To elucidate the structure–activity relationship of the affinity of C1P for cPLAα in lipid environments, we prepared a series of C1P analogs containing structural modifications in the hydrophilic parts and subjected them to surface plasmon resonance (SPR). The results suggested the

  神经酰胺 1-磷酸 (C1P) 是一种脂质介质，可特异性结合并激活胞质磷脂酶 Aα (cPLAα)。为了阐明脂质环境中 C1P 对 cPLAα 亲和力的构效关系，我们制备了一系列亲水部分含有结构修饰的 C1P 类似物，并对它们进行表面等离子共振 (SPR)。结果表明，C1P 结构中的酰胺基、3-OH 基和磷酸基上存在 cPLAα 的特异性结合位点。特别是，二氢-C1P 对 cPLAα 表现出增强的亲和力，表明 3-羟基的氢键能力对于与 cPLAα 的相互作用很重要。这项研究有助于了解 C1P 的特定结构部分对原子水平上与 cPLAα 相互作用的影响，并可能有助于设计调节 cPLAα 激活的药物。
• BROMODOMAIN-INHIBITING COMPOUNDS AND PHARMACEUTICAL COMPOSITION COMPRISING SAME FOR PREVENTING OR TREATING A CANCER
  申请人：KAINOS MEDICINE, INC.

  公开号：US20170174702A1

  公开（公告）日：2017-06-22

  Provided is a novel compound having bromodomain and extra terminal domain (BET) protein inhibiting activities, and a pharmaceutical composition comprising the same which can be useful for prevention or treatment of precancerous transformation or cancer.
• US9884874B2
  申请人：——

  公开号：US9884874B2

  公开（公告）日：2018-02-06
• IOOC Route to Substituted Chiral Pyrrolidines. Potential Glycosidase Inhibitors
  作者：Eliezer Falb、Yosi Bechor、Abraham Nudelman、Alfred Hassner、Amnon Albeck、Hugo E. Gottlieb

  DOI：10.1021/jo9815094

  日期：1999.1.1

  Branched-chain five-membered ring aza-sugar analogues, synthesized from amino acids by an intramolecular oxime-olefin cycloaddition reaction, the IOOC route, were found to be selective glycosidase inhibitors. The derivative 2,4(S)-di(hydroxymethyl)-3(S)-aminopyrrolidine, obtained from D-serine, was about 1 order of potency more active than its enantiomer obtained from L-serine.