3-hydroxy-1-isopropyl-4,4-dimethyl-3-phenyl-azetidin-2-one | 64201-03-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: 3-hydroxy-1-isopropyl-4,4-dimethyl-3-phenyl-azetidin-2-one
• 英文别名: 1-Isopropyl-3-phenyl-3-hydroxy-4,4-dimethylazetidin-2-on；1-Isopropyl-3-hydroxy-3-phenyl-4,4-dimethylazetidin-2-one；3-hydroxy-4,4-dimethyl-3-phenyl-1-propan-2-ylazetidin-2-one
• CAS: 64201-03-2
• 化学式: C₁₄H₁₉NO₂
• 分子量: 233.31
• InChiKey: JPSJFSPZJNFLNV-UHFFFAOYSA-N

物化性质

• 熔点：
  140-141 °C
• 沸点：
  383.1±42.0 °C(Predicted)
• 密度：
  1.118±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N,N-diisopropyl-2-oxo-2-phenylacetamide 生成 3-hydroxy-1-isopropyl-4,4-dimethyl-3-phenyl-azetidin-2-one
  参考文献：
  名称：

  羰基酰胺晶体的光学活性

  摘要：

  众所周知，由非手性分子组成的氧代酰胺晶体可以通过高压汞灯的照射光化学转化为光学活性的 β-内酰胺。虽然氧代酰胺晶体属于对映体 D2 类，但目前无法检测到其光学活性。我们使用HAUP（高精度通用旋光仪）方法成功测量了氧代酰胺晶体的回转张量分量：g11 = -3.5 × 10-4 (-79°/mm), g22 = -1.4 × 10-4 (-32°/mm), g33 = -3.0 × 10-4 (-68°/mm) 在 305 K，其中旋光度在括号中表示。直接实验证明，该反应体系中反应物和产物的旋光活性在整个光环化过程中保持不变。

  DOI：

  10.1021/ja9620189

文献信息

• Asymmetric induction during photocyclization of chiral and achiral α-oxoamides within achiral zeolites
  作者：Arunkumar Natarajan、V. Ramamurthy

  DOI：10.1039/b611387g

  日期：——

  gamma-hydrogen transfer. While in benzene the major product is oxazolidinone, within an MY zeolite, the main product is a beta-lactam. In this investigation, we have focused our attention on asymmetric induction in the formation of the beta-lactam product. Two approaches--using a chiral inductor and chiral auxiliary--have been employed. While in solution, in the presence of chiral inductors, achiral

  已经在沸石中研究了能够进行γ-氢转移的31种α-氧代酰胺的光化学反应。激发后，这些分子在溶液中产生两种产物-β-内酰胺和恶唑烷酮-两者都是由γ-氢转移产生的。苯中的主要产物是恶唑烷酮，而MY沸石中的主要产物是β-内酰胺。在这项研究中，我们将注意力集中在β-内酰胺产物形成中的不对称诱导上。已经采用了两种方法-使用手性感应剂和手性辅助剂。在溶液中，在手性诱导剂的存在下，非手性α-氧酰胺可产生对映选择性为零的β-内酰胺。在沸石中，ee高达44％。带有手性助剂的α-氧代酰胺在溶液中对β-内酰胺的非对映选择性低于5％，而在沸石中，相同的α-氧代酰胺使产品的de's高达83％。沸石的如此显着影响归因于碱金属离子与反应物α-氧代酰胺的相互作用以及沸石内部的封闭环境。在这一阶段，我们还不能提供具有预测能力的模型，需要进一步的工作来理解这种有价值的非对称归纳策略。
• Medium Effects on Zwitterionic-Biradicaloid Intermediates from Two Phenyl--α-oxoamides. Irradiations in Fluid and Solid Protic Media, Neat Solid Phases, and the Solid, Smectic and Isotropic Phases of a Completely Saturated Phosphonium Salt at Different Te
  作者：Carlos A. Chesta、Mathew George、Chuping Luo、Richard G. Weiss

  DOI：10.1562/2006-07-28-ra-988

  日期：——

  The photochemical processes of two NN-dialkyl phenyl-alpha-oxo-amides, NN-diisopropyl phenyl-alpha-oxoamide (1) and NN-dibenzyl phenyl-a-oxoamide (2), are investigated at different temperatures in methanol and ethylene glycol (to probe the influences of H-bonding and viscosity), in the solid phase Of D-sorbitol at room temperature (to compare with the results in the liquid alcohols and to assess the influence of a poorly organized "stiff" environment), in the neat solid phase (to probe the influence of well-ordered, "stiff" matrices), and in the solid, smectic A(2) and isotropic phases of methyl-tris-tetradecylphosphonium tetrafluoroborate (1P14BF4) (to assess the ability of the intermediates to respond to subtle changes in the order and polarity of their local environments). From differences between the activation parameters for product pathways from irradiations in methanol and in 1P14BF4, we conclude that the zwitterionic pre-product intermediate from 1I is much more sensitive to the polarity, viscosity and order of its local environment than is the isomeric preproduct biradicaloid intermediate or either of the pre-product intermediates from 2. A very sensitive balance among the medium parameters, as well as internal steric and electronic factors of 1 and 2, controls the reactive pathways of the photochernically generated intermediates.
• Photochemical reactions of .alpha.-oxo amides. Norrish type II reactions via zwitterionic intermediates
  作者：Hiromu Aoyama、Masami Sakamoto、Keiko Kuwabara、Katsuhiko Yoshida、Yoshimori Omote

  DOI：10.1021/ja00345a049

  日期：1983.4
• Chesta, Carlos A.; Whitten, David G., Journal of the American Chemical Society, 1992, vol. 114, # 6, p. 2188 - 2197
  作者：Chesta, Carlos A.、Whitten, David G.

  DOI：——

  日期：——
• AOYAMA, HIROMU;SAKAMOTO, MASAMI;KUWABARA, KEIKO;YOSHIDA, KATSUHIKO;OMOTE,+, J. AMER. CHEM. SOC., 1983, 105, N 7, 1958-1964
  作者：AOYAMA, HIROMU、SAKAMOTO, MASAMI、KUWABARA, KEIKO、YOSHIDA, KATSUHIKO、OMOTE,+

  DOI：——

  日期：——