methyl 5-oxo-1-(2-oxo-2-phenylethyl)cyclohexa-3-enecarboxylate | 1408318-26-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 5-oxo-1-(2-oxo-2-phenylethyl)cyclohexa-3-enecarboxylate
• 英文别名: Methyl 5-oxo-1-phenacylcyclohex-3-ene-1-carboxylate；methyl 5-oxo-1-phenacylcyclohex-3-ene-1-carboxylate
• CAS: 1408318-26-2
• 化学式: C₁₆H₁₆O₄
• 分子量: 272.301
• InChiKey: NENDOWBKDMKLDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 5-oxo-1-(2-oxo-2-phenylethyl)cyclohexa-3-enecarboxylate 在 4-二甲氨基吡啶 、 水 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 5-(((cyclohexylideneamino)oxy)carbonyl)-5-(2-oxo-2-phenylethyl)cyclohex-2-enone
  参考文献：
  名称：

  Design and Synthesis of a Photoaromatization-Based Two-Stage Photobase Generator for Pitch Division Lithography

  摘要：

  The synthesis of a two-stage photobase generator (PBG) based on photoinduced aromatization is described. This material was designed for use in resolution-enhanced photolithography. Computer modeling predicts that a delay in the onset of base generation can lead to improved image quality. This delay can be realized by a PBG that must undergo two sequential photoreactions for each molecule of base generated Toward that end, latent PBGs were designed that are oxime esters of aliphatic acids, which undergo Norrish type II reactions to yield oxime esters of aromatic acids that are efficient PBGs.

  DOI：

  10.1021/jo3021488
• 作为产物：
  描述：

  methyl 3-methoxycyclohexa-2,5-dienecarboxylate 在 水 、 对甲苯磺酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 正己烷 为溶剂， 反应 4.25h， 生成 methyl 5-oxo-1-(2-oxo-2-phenylethyl)cyclohexa-3-enecarboxylate
  参考文献：
  名称：

  Design and Synthesis of a Photoaromatization-Based Two-Stage Photobase Generator for Pitch Division Lithography

  摘要：

  The synthesis of a two-stage photobase generator (PBG) based on photoinduced aromatization is described. This material was designed for use in resolution-enhanced photolithography. Computer modeling predicts that a delay in the onset of base generation can lead to improved image quality. This delay can be realized by a PBG that must undergo two sequential photoreactions for each molecule of base generated Toward that end, latent PBGs were designed that are oxime esters of aliphatic acids, which undergo Norrish type II reactions to yield oxime esters of aromatic acids that are efficient PBGs.

  DOI：

  10.1021/jo3021488

文献信息

• Study of a Two-Stage Photobase Generator for Photolithography in Microelectronics
  作者：Nicholas J. Turro、Yongjun Li、Steffen Jockusch、Yuji Hagiwara、Masahiro Okazaki、Ryan A. Mesch、David I. Schuster、C. Grant Willson

  DOI：10.1021/jo302149u

  日期：2013.3.1

  production of microelectronic chips. In the present system, the excitation of 1 results in a Norrish type II intramolecular hydrogen abstraction to generate a 1,4-biradiacal that undergoes cleavage to form 2 and acetophenone (Φ ∼ 0.04). In the second step, excitation of 2 causes cleavage of the oxime ester (Φ = 0.56) followed by base generation after reaction with water.

  描述了对两级光碱产生剂（PBG）的光化学的研究。潜在的PBG（1）吸收光子（第一步）会产生PBG（2）。在水的存在下照射2会产生碱（第二步）。此双光子序列（1个+ ħ ν→ 2 + ħ ν→碱）是光致抗蚀剂的设计间距分割技术，即加倍投影光刻法用于生产微电子芯片的分辨率的方法的一个重要组成部分。在本系统中，1的激发会导致Norrish II型分子内氢提取，从而生成1，4-双radi醛，然后裂解形成2和苯乙酮（Φ〜0.04 ）。在第二步中，激发2会裂解肟酯（Φ= 0.56），然后在与水反应后生成碱。
• Design and Synthesis of a Photoaromatization-Based Two-Stage Photobase Generator for Pitch Division Lithography
  作者：Yuji Hagiwara、Ryan A. Mesch、Takanori Kawakami、Masahiro Okazaki、Steffen Jockusch、Yongjun Li、Nicholas J. Turro、C. Grant Willson

  DOI：10.1021/jo3021488

  日期：2013.3.1

  The synthesis of a two-stage photobase generator (PBG) based on photoinduced aromatization is described. This material was designed for use in resolution-enhanced photolithography. Computer modeling predicts that a delay in the onset of base generation can lead to improved image quality. This delay can be realized by a PBG that must undergo two sequential photoreactions for each molecule of base generated Toward that end, latent PBGs were designed that are oxime esters of aliphatic acids, which undergo Norrish type II reactions to yield oxime esters of aromatic acids that are efficient PBGs.