1,1-dimethylethyl 2-oxo-3-(phenylmethyl)-1-piperidinecarboxylate | 142929-60-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1,1-dimethylethyl 2-oxo-3-(phenylmethyl)-1-piperidinecarboxylate
• 英文别名: tert-butyl 3-benzyl-2-oxopiperidine-1-carboxylate
• CAS: 142929-60-0
• 化学式: C₁₇H₂₃NO₃
• 分子量: 289.375
• InChiKey: RVZVTOIHOFJTMJ-UHFFFAOYSA-N

物化性质

• 沸点：
  433.6±14.0 °C(Predicted)
• 密度：
  1.115±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,1-dimethylethyl 2-oxo-3-(phenylmethyl)-1-piperidinecarboxylate 在 水 、 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 α-<3-<<(1,1-dimethylethoxy)carbonyl>amino>propyl>benzenepropanoic acid
  参考文献：
  名称：

  WO2020086595A5

  摘要：

  公开号：

  WO2020086595A5
• 作为产物：
  描述：

  溴甲苯 、 1-Boc-2-哌啶酮 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 5.5h， 以48%的产率得到1,1-dimethylethyl 2-oxo-3-(phenylmethyl)-1-piperidinecarboxylate
  参考文献：
  名称：

  WO2020086595A5

  摘要：

  公开号：

  WO2020086595A5

文献信息

• Activation of CF Bonds in Preference to CI Bonds: Difluoromethylation of Lithium Enolates with Trifluoromethyl Iodide
  作者：Koichi Mikami、Yuichi Tomita、Yoshimitsu Itoh

  DOI：10.1002/anie.201000435

  日期：——

  it: A conceptually new CF activation/CC formation and its mechanism are described. Surprisingly, a reaction with Li‐enolates and trifluoromethyl iodide gave (alpha)‐difluoromethyl product via CF bond cleavage in preference to the weaker CI bond of trifluoromethyliodide. This reaction proceeds without the use of any late transition‐metal catalyst (see scheme; LHMDS=lithium hexamethyldisilaxide).

  我拥有它：描述了概念上新的CF激活/ CC的形成及其机理。出人意料的是，与烯醇盐和三氟甲基碘的反应优先通过CF键裂解产生α-二氟甲基产物，而不是弱于三氟甲基碘的CI键。该反应在不使用任何后期过渡金属催化剂的情况下进行（参见方案； LHMDS =六甲基二硅酸锂）。
• Umpolung of Fluoroform by CF Bond Activation: Direct Difluoromethylation of Lithium Enolates
  作者：Toshiaki Iida、Ryota Hashimoto、Kohsuke Aikawa、Shigekazu Ito、Koichi Mikami

  DOI：10.1002/anie.201203588

  日期：2012.9.17

  Double agent: The direct α‐difluoromethylation of lithium enolates using an umpolung form of fluoroform as a difluoromethyl carbocation equivalent leads to an all‐carbon quaternary center. Late transition metals are not necessary and the reaction involves activation of inert CF bonds with subsequent CC bond formation.

  双重作用剂：使用氟酚的呈峰状形式作为二氟甲基碳正离子当量，直接对烯醇锂进行α-二氟甲基化，可形成一个全碳四元中心。后过渡金属是没有必要的，该反应涉及的惰性C活化 F键与今后的C  C键的形成。
• Analogs of the .delta. opioid receptor selective cyclic peptide [cyclic][2-D-penicillamine,5-D-penicillamine]-enkephalin: 2',6'-dimethyltyrosine and Gly3-Phe4 amide bond isostere substitutions
  作者：Nizal S. Chandrakumar、Awilda Stapelfeld、Patrick M. Beardsley、Oscar T. Lopez、Bridget Drury、Elizabeth Anthony、Michael A. Savage、L. Neil Williamson、Melvin Reichman

  DOI：10.1021/jm00094a002

  日期：1992.8

  In order to develop systemically-active opioid peptides, the delta-selective, opioid pentapeptide [D-Pen2,D-Pen5]-enkephalin (DPDPE) was modified by esterification and by substitution of 2,6-dimethyltyrosine for tyrosine to yield 4. Compound 4 was on the order of 8- and 800-fold more active than DPDPE in both delta and mu-opioid radioligand binding assays, respectively, in rat neural membrane suspensions. Compound 4 was considerably more potent than DPDPE at inhibiting contractions of electrically-stimulated mouse vas deferens in vitro, and this effect was very sensitive to naltrindole, a delta-selective opioid antagonist. These observations can be taken as indication that 4 exerts its effects through delta-opioid receptors. This interpretation is supported by the finding that the EC50 value of 4 derived in the smooth muscle assay is very similar to that derived in NG108-15 neuroblastoma cells, a preparation devoid of mu-receptors. Unlike DPDPE, 4 exhibited significant, naloxone-sensitive, antinociceptive activity when administered systemically, as measured by inhibition of phenylbenzquinone-induced stretching in mice (ED50 = 2.1 mg/kg). Compound 4 also displayed significant antinociceptive activity following systemic administration as measured by its action in mice to increase latencies for tail withdrawal from radiant heat (ED50 = 50 mg/kg). Compound 4 did not produce morphine-like discriminative stimulus effects in rats trained to discriminate 3.0 mg/kg morphine from vehicle at doses ranging from 30 to 120 mg/kg. This observation can be interpreted as indication that within this dosage range there is an absence of morphine-like subjective effects. Physical dependence, however, could be induced in mice at higher doses of 4 under a progressively-graded, 4-day dose regimen. Congeners of 4 with amide bond surrogates for the Gly-Phe amide bond (oxymethylene, trans-double bond, and bismethylene isosteres) in the cyclic core of DPDPE were prepared in an attempt to increase the antinociceptive activity of 4. While some of the were active in the in vitro assays, they did not display significant antinociceptive activity following systemic administration. The preparation of all the compounds was accomplished by solution-phase methods. The which might underlie the biological and systemic activity of 4 are discussed.
• No Catalyst, Radical Initiator and Photochemical Irradiation Approach to Direct α-Trifluoromethylation of Lithium Enolates
  作者：Koichi Mikami、Yuichi Tomita、Toshiaki Iida、Ryota Hashimoto、Yoshimitsu Itoh

  DOI：10.3987/com-13-s(s)95

  日期：——

  Heterocyclic lactam lithium enolates exploit an access to the electrophilic radical alpha-trifluoromethylation without catalyst/radical initiator/photochemical irradiation.